cas 122-88-3, 4-Chlorophenoxyacetic acid | Articles data

Articles about 122-88-3Total 102 be found

Article title
Article abstract
Author
Journal number and time
Download

Facile microwave synthesis, structural diversity and herbicidal activity of six novel alkaline-earth metal complexes (AECs) based on skeletal isomerization chlorophenoxyacetic acids
Six novel AECs of [Sr(o-CPA)2(H2O)4]·(o-CPA) 1, [Ba(o-CPA)2(H2O)]·H2O 2, [Sr(m-CPA)2(H2O)4]·(m-CPA) 3, [Ba(m-CPA)2(H2O)4]2·2(m-CPA)·H2O 4, [Sr(p-CPA)2(H2O)] 5 and [Ba(p-CPA)2(H2O)] 6 (o-CPA = 2-chlorophenoxyacetic acid, m-CPA = 3-chlorophenoxyacetic acid and p-CPA = 4-chlorophenoxyacetic acid) were synthesized by a facile microwave-assistant reaction. The solid-state structures were well established by X-ray crystallography and routine analyses of Fourier transform infrared, elemental analysis, field emission scanning electron microscope (FESEM) and thermogravimetric analysis. The structure data reveal that complexes of 1, 3 and 4 are one-dimensional chains with a zigzag arrangement, while 2, 5 and 6 are (4, 4) rhomboid two-dimensional grid structures. It is noticed that the carboxyl group in these complexes displays multiple coordination modes of μ2-η1:η1 (1, 2, 3, 4, 5 and 6), μ3-η1:η2 (1, 2, 3 and 4), μ2-η1:η2 (2), μ3-η2:η2 (5 and 6). Interestingly, the oxygen atoms of flexible -OCH2- in phenoxy groups take part in coordination behavior with metal centers through the rotation of the C-O and C-C bonds in complexes 2, 5 and 6, while only carboxyl group coordination can be found in complexes 1, 3 and 4. FESEM images indicate that the surface appearances of complexes are totally different from ligands after coordination. All ligands and complexes were evaluated for activity as plant-growth inhibitors against Amaranth (Amaranthus spp.) and barnyard grass. Compared with ligands, complexes 1, 3 and 4 exhibited better response index (RI) values of Shoot elongation against barnyard grass. Moreover, complexes 1, 3 and 4 demonstrated a higher inhibitory activity than 2, 5 and 6. It is significant to develop a new kind of environmentally-friendly herbicide based on these kinds of complexes for their low toxicity and high efficiency.
Xu, Xiuling,Hu, Fan,Ma, Yuwei,Gao, Jinming,Shuai, Qi
p. 4155 - 4166
(2018)
Read Online

Stability of solid dosage forms. II. Hydrolysis of meclofenoxate hydrochloride in commercial tablets
The kinetics of hydrolysis of meclofenoxate hydrochloride (MF-HCl) in commercial tablets were studied in comparison with those of the pure solid. MF-HCl in tablets was found to be decomposed by water vapor in the same way as the pure solid. At a humidity above the critical relative humidity (CRH) of the system, the degradation ratio, x could be correlated to time by the equation: x = kt(n) where k and n are parameters. At humidities below the CRH, on the other hand, the degradation did not conform to this equation because of the fast decomposition at the initial stage. The stability of several commercial MF-HCl tablets was studied, and some excipients such as magnesium carbonate were found to reduce the stability of the drug.
Yoshioka,Shibazaki,Ejima
p. 2513 - 2517
(1983)
Read Online

Facile synthesis of highly biocompatible folic acid-functionalised SiO2 nanoparticles encapsulating rare-earth metal complexes, and their application in targeted drug delivery
Mesoporous silica core-shell nanospheres encapsulating a rare-earth metal complex (RC) were first synthesised through a facile W/O (water in oil) inverse microemulsion method. In order to achieve targeted complex delivery, folic acid (FA) was used as the targeting component due to its high affinity for over-expressed folate receptors (FRs) in cancer cells. The RC2@SiO2-FA nanospheres were characterised via ultraviolet-visible light absorption spectroscopy (UV-vis spectroscopy), dynamic light scattering (DLS), scanning electron microscopy (SEM) and transmission electron microscopy (TEM). A microwave method was used to synthesise five RC cores based on 4-chlorophenoxyacetic acid, and their crystal structures were further confirmed using X-ray diffraction. The five RC cores have the following chemical formulae: [Er2(p-CPA)6(H2O)6] RC1, [Ho2(p-CPA)6(H2O)6] RC2, [Sm(p-CPA)3(H2O)] RC3, [Pr(p-CPA)3(H2O)]·3H2O RC4 and [Ce(p-CPA)3(H2O)2]·2H2O RC5. The carboxyl groups showed two kinds of coordination modes, namely μ2-η1:η1 and μ2-η1:η2, among RC1-RC5. The flexible -OCH2COO- spacer group, which can undergo rotation of its C-O and C-C bonds, offered great potential for structural diversity. In vivo experiments revealed that the nanospheres exhibited no obvious cytotoxicity on HepG2 cells and 293 T cells, even at concentrations of up to 80 μg mL-1. Nevertheless, all of the RC cores showed a certain degree of anti-tumour efficacy; in particular, RC2 showed the strongest cytotoxicity against HepG2 cells. Interestingly, the cytotoxicity of all of the RC2@SiO2-FA nanospheres was higher than that of lone RC2. These types of FA-targeted mesoporous silica nanocarriers can be used for the delivery of anti-tumour RC, and provide a basis for the further study of affordable non-platinum-based complexes.
Xu, Xiuling,Hu, Fan,Shuai, Qi
p. 15424 - 15433
(2017)
Read Online

Stability of solid dosage forms. I. Hydrolysis of meclofenoxate hydrochloride in the solid state
-
Yoshioka,Shibazaki,Ejima
p. 3734 - 3741
(1982)
Read Online

Analysis of meclofenoxate and its degradation products by high performance liquid chromatography
-
Tatsuhara,Tabuchi
p. 779 - 782
(1980)
Read Online

-
-
Jones,Richardson
p. 3939
(1956)
Read Online

Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl)isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents
Inflammation is the complex biological response of vascular tissues, which is partly determined by prostaglandins (PLA2). The cyclooxygenase (COX) enzyme exists in two isoforms: COX-1 and COX-2 and by the action of this, the PGs are produced. Besides, nonsteroidal anti-inflammatory drugs (NSAIDs) are therapeutic agents useful in the treatment of inflammation. Encouraged by this, the new derivatives of N'(2-phenoxyacetyl)nicotinohydrazide 9(a-e) and N'(2-phenoxyacetyl)isonicotinohydrazide 10(a-e) were designed, synthesized, characterized, and identified as remarkable anti-inflammatory and analgesic agents. These compounds were prepared in a series of steps starting with different phenol derivatives. Among the series, compound (10e) showed the highest IC50 value for COX-1 inhibition, whereas compounds (9e) and (10e) exhibited the highest COX-2SI. Further, molecular Docking Studies have been performed for the potent compound to check the three-dimensional geometrical view of the ligand binding to the targeted enzymes.
Al-Ostoot, Fares Hezam,Khanum, Shaukath Ara,M, Pallavi H,Vivek, Hamse Kameshwar
(2021/09/14)

Targeting HIF-1α by newly synthesized Indolephenoxyacetamide (IPA) analogs to induce anti-angiogenesis-mediated solid tumor suppression
Background: Hypoxic microenvironment is a common feature of solid tumors, which leads to the promotion of cancer. The transcription factor, HIF-1α, expressed under hypoxic conditions stimulates tumor angiogenesis, favoring HIF-1α as a promising anticancer agent. On the other hand, synthetic Indolephenoxyacetamide derivatives are known for their pharmacological potentiality. With this background here, we have synthesized, characterized, and validated the new IPA (8a–n) analogs for anti-tumor activity. Methods: The new series of IPA (8a–n) were synthesized through a multi-step reaction sequence and characterized based on the different spectroscopic analysis FT-IR, 1H, 13C NMR, mass spectra, and elemental analyses. Cell-based screening of IPA (8a–n) was assessed by MTT assay. Anti-angiogenic efficacy of IPA (8k) validated through CAM, Rat corneal, tube formation and migration assay. The underlying molecular mechanism is validated through zymogram and IB studies. The in vivo anti-tumor activity was measured in the DLA solid tumor model. Results: Screening for anti-proliferative studies inferred, IPA (8k) is a lead molecule with an IC50 value of ?5?μM. Anti-angiogenic assays revealed the angiopreventive activity through inhibition of HIF-1α and modulation downstream regulatory genes, VEGF, MMPs, and P53. The results are confirmative in an in vivo solid tumor model. Conclusion: The IPA (8k) is a potent anti-proliferative molecule with anti-angiogenic activity and specifically targets HIF1α, thereby modulates its downstream regulatory genes both in vitro and in vivo. The study provides scope for new target-specific drug development against HIF-1α for the treatment of solid tumors. Graphic abstract: [Figure not available: see fulltext.].
Al-Ostoot, Fares Hezam,Sherapura, Ankith,V, Vigneshwaran,Basappa, Giridhara,H.K, Vivek,B.T, Prabhakar,Khanum, Shaukath Ara
p. 1328 - 1343
(2021/05/03)

Discovery, synthesis and biological characterization of a series of: N -(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1 H -pyrazol-5-yl)acetamide ethers as novel GIRK1/2 potassium channel activators
The present study describes the discovery and characterization of a series of N-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1H-pyrazol-5-yl)acetamide ethers as G protein-gated inwardly-rectifying potassium (GIRK) channel activators. From our previous lead optimization efforts, we have identified a new ether-based scaffold and paired this with a novel sulfone-based head group to identify a potent and selective GIRK1/2 activator. In addition, we evaluated the compounds in tier 1 DMPK assays and have identified compounds that display nanomolar potency as GIRK1/2 activators with improved metabolic stability over the prototypical urea-based compounds. This journal is
Alnouti, Yazen,Aretz, Christopher D.,Chhonker, Yashpal S.,Dhuria, Nikilesh V.,Du, Yu,Gautam, Nagsen,Hopkins, Corey R.,Kumar, Sushil,Lesiak, Lauren,Sharma, Swagat,Weaver, C. David
p. 1366 - 1373
(2021/09/28)

Juvenile hormone mimics with phenyl ether and amide functionality to be insect growth regulators (IGRs): synthesis, characterization, computational and biological study
A series of substituted phenyl ethers derivatives as juvenile hormone (JH) mimics (V1-V8) have been synthesized. Substituted phenoxyacetic acid and amino acid ethyl ester hydrochloride were prepared using NaOH, SOCl2. DCC method has been used for amide linkage. The structure of prepared compounds has been confirmed by Fourier Transform Infra-Red (FT-IR), Electrospray ionization-Mass spectrometry (ESI-MS), Proton and Carbon-13 nuclear magnetic resonance (1H-NMR, 13C-NMR) spectroscopic techniques. Biological efficacy of synthesized analogs has been carried out under laboratory conditions. Galleria mellonella (honey bee pest) has been chosen as testing insect. Juvenile hormone (JH) activity of synthesized compounds has been tested at different concentrations and compared with the standard juvenile hormone analogs (JHAs) pyriproxyfen (M1) and fenoxycarb (M2) against the fifth larval instar of G. mellonella. Compound ethyl 2-[2-(4-methylphenoxy)aminoacetyl]-3-phenyl-propanoate (V6) exhibited better activity among all the synthesized compounds (V1-V8) with LC50 and LC90 values of 0.11 mg/mL and 0.56 mg/mL respectively. Compounds showed insect growth regulating (IGR) activity at lower concentrations. In silico screening of all synthesized compounds with the W-cavity of juvenile hormone-binding protein (JHBP) of insect G. mellonella has been carried out. Chemical reactivity of synthesized series has been studied using DFT/B3LYP/6-311 + G(d,2p) method. Non-toxic behavior of molecules has also been observed from ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) study using discovery studio client 3.0. Communicated by Ramaswamy H. Sarma.
Awasthi, Pamita,Devi, Vandna
(2021/10/12)

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.
Huang, Hao,Liu, Jian-Min,Shu, Lei,Wang, Man-Man,Yan, Yi-Le,Zhang, Da-Yong,Zhang, Jian-Qiu
p. 233 - 247
(2020/03/27)

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action
In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
Lei, Kang,Li, Pan,Yang, Xue-Fang,Wang, Shi-Ben,Wang, Xue-Kun,Hua, Xue-Wen,Sun, Bin,Ji, Lu-Sha,Xu, Xiao-Hua
p. 10489 - 10497
(2019/10/02)

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones
We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.
Wang, Zexu,Wu, Xiaofan,Li, Zhining,Huang, Zedu,Chen, Fener
supporting information
p. 3575 - 3580
(2019/04/14)

Decarboxylative hydrazination of unactivated carboxylic acids by cerium photocatalysis
We report the cerium photocatalyzed radical decarboxylative hydrazination of carboxylic acids with di-tert-butylazodicarboxylate (DBAD). The operationally simple protocol provides rapid access to synthetically useful hydrazine derivatives and overcomes current scope limitations in the photoredox-catalyzed decarboxylation of carboxylic acids.
Yatham, Veera Reddy,Bellotti, Peter,K?nig, Burkhard
supporting information
p. 3489 - 3492
(2019/03/26)

N-(3-(2-(4-CHLOROPHENOXY)ACETAMIDO)BICYCLO[1.1.1]PENTAN-1-YL)-2-CYCLOBUTANE-1-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ATF4 INHIBITORS FOR TREATING CANCER AND OTHER DISEASES
The invention is directed to substituted bridged cycloalkane derivatives. Specifically, the invention is directed to compounds according to Formula (I) wherein X, a, b, C, D, L2,L3, Y1, Y2, R2, R4, R5, R6, z2, z4, z5, and z6 are as defined herein, and salts thereof. The invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to compounds for use in methods of inhibiting the ATF4 (activating transcription factor 4) pathway and treatment of disorders associated therewith, such as e.g. cancer, neurodegenerative diseases and many other diseases, using a compound of the invention or a pharmaceutical composition comprising a compound of the invention. Preferred compounds of the invention are N-(3-(2-(4-chlorophenoxy) acetamido)bicyclo[1.1.1]pentan-l-yl)-2-cyclobutane-l-carboxamide derivatives and related compounds.
-
Page/Page column 84

(2019/01/21)

A method for preparing chloro-benzene oxygen carboxylic acid (by machine translation)
The invention provides a method for preparing carboxylic acid chloro-benzene oxygen, comprising the following steps: S1) phenoxy fatty alcohol in the catalyst B A and under the action of the catalyst, and the chlorinating agent to 2 bit and/or 4 bit selective chlorination reaction, to obtain chloro-benzene oxygen fatty alcohol; said catalyst A is Lewis acid; said catalyst B is C5 - 22 of the thioether, thiazole, isothiazole, thiophene or their halogenated derivatives; S2) [...] fatty alcohol and water, under the action of a catalyst, and an oxidizing agent for the selective catalytic oxidation reaction, get chloro-benzene oxygen carboxylic acid. The invention through the re-design of the process route, the catalyst and the chlorinating agent fine screening, effectively reduces the energy consumption, the selectivity of the dichloride to improve at the same time avoiding the losses of the active ingredient, the resulting chloro-benzene oxygen carboxylic acid content can be up to 98.5% or more, the total yield can be up to 99% or more. (by machine translation)
-
(2019/01/08)

The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death
Tumor microenvironment is a complex multistep event which involves several hallmarks that transform the normal cell into cancerous cell. Designing the novel antagonistic molecule to reverse the tumor microenvironment with specific target is essential in modern biological studies. The novel 4-phenyl-2-phenoxyacetamide thiazole analogues 8a-ab were synthesized in multistep process, then screened and assessed for cytotoxic and anti-proliferative effects in vitro against multiple cancer cells of different origin such as MCF-7, A549, EAC and DLA cells which revealed that compound 8f with fluoro and methyl substitute has potential cytotoxic efficacy with an average IC50 value of ? 13 μM. The mechanism of cytotoxicity assessed for anti-tumor studies both in ascites and solid tumor models in-vivo inferred the regressed tumor activity. This is due to changes in the cause of tumor microenvironment with crackdown of neovascularization and evoking apoptosis process as assessed by CAM, corneal vascularization and apoptotic hallmarks in 8f treated cells. The molecular gene studies inferred involvement of HIF-1upregulation and stabilization of p53 which are interlinked in signaling as conferred by immunoblot analysis.
Mohammed, Yasser Hussein Eissa,Malojirao, Vikas H.,Thirusangu, Prabhu,Al-Ghorbani, Mohammed,Prabhakar,Khanum, Shaukath Ara
p. 1826 - 1839
(2017/11/16)

CHEMICAL COMPOUNDS AS ATF4 PATHWAY INHIBITORS
The invention is directed to substituted bridged cycloalkane derivatives. Specifically, the invention is directed to compounds according to Formula (IIIQ): wherein X6', a, b, C8', D8', L82', L83', R81', R82', R83', R84', R85', R86', z82', z84', z85', and z86' are as defined herein; or salts thereof. The compounds of the invention are inhibitors of the ATF4 pathway. Accordingly, invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting the ATF4 pathway and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
-
(2019/01/06)

A phenoxy carboxylic acid herbicide preparation method (by machine translation)
The invention provides a phenoxy carboxylic acid herbicide preparation method, including: S1, will be [...], alkaline substance mixed with the chlorinated carboxylic acid ester, in the one-pot condensation reaction in anhydrous system, phenoxy carboxylic acid ester obtained; the ClR states the chloro- carboxylic acid ester of the formula is1 COOR, R1 Is C1 - 3 alkylene or alkylidene, R is C1 - 10 alkyl or C3 - 10 cycloalkyl; S2, the [...] ester in the 1st and 2nd catalyst under the action of a catalyst, with the chlorinating agent to carry out the selective chlorination of, get [...] ester; the Lewis acid catalyst is selected from 1st, 2nd catalyst is C5 - 22 of the thioether compound, thiazole compound, isothiazole compound or thiophene compound; S3, will the [...] ester to acid hydrolysis reaction, as shown in formula I phenoxy carboxylic acid herbicide, R3 Is H, Cl or CH3 . This invention can improve the quality of the products and the operating environment of production, three waste low. (by machine translation)
-
(2019/01/08)

Preparation method of phenoxycarboxylic acid herbicide
The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out reaction of anhydrous phenol with an active metalto form phenoxide, and carrying out condensation reaction of the phenoxide with chlorocarboxylic ester to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula ofClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 of cycloalkyl; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent in the presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H,Cl or CH3. The preparation method can improve the product quality and the operation environment of the production site, and has low quantity of three wastes.
-
(2019/01/08)

Preparation method of phenoxy carboxylic acid herbicide
The invention provides a preparation method of a phenoxy carboxylic acid herbicide, comprising the following steps: S1, carrying out a condensation reaction between a phenolic compound and hydroxycarboxylic ester under the action of a catalyst so as to obtain phenoxycarboxylic ester, wherein the catalyst is one or more of protonic acid, solid acid and a supported catalyst; S2, carrying out 2- and/or 4- selecting chlorination reaction between phenoxycarboxylic ester and a chloridizing agent in the presence of a first catalyst and a second catalyst, so as to obtain chlorinated phenoxycarboxylicester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is selected from a C5-C22 thioether compound, a C5-C22 thiazole compound, a C5-C22 isothiazole compound or a C5-C22 thiophene compound; and S3, carrying out an acidolysis reaction on chlorinated phenoxycarboxylic ester so as to obtain the phenoxy carboxylic acid herbicide. By the method, product quality and thelive environment of production can be improved, and ''three wastes (waste gas, waste water and industrial residue)'' are minimized.
-
(2019/01/08)

Preparation method of phenoxycarboxylic acid herbicide
The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol withchlorocarboxylic ester under the action of an alkaline substance to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 cycloalkyl; S2, carrying out selective chlorination of phenoxycarboxylic ester with a chlorinating agent under the action of a first catalyst and a second catalyst, to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, the second catalyst is C5-22 thioether compounds, thiazole compounds, isothiazole compounds or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester, to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H, Cl or CH3. The preparation method can improve the product quality and the operation environment of a production site, and has low quantity of three wastes.
-
(2019/01/08)

Novel pyrazolone derivatives and corresponding europium(III) complexes: Synthesis and properties research
A series of pyrazolone derivatives ligands L1?7 were successfully synthesized and validated by 1H NMR and MS, corresponding europium complexes [EuL1?7(NO3)2]NO3·EtOAc were synthesized. Physico-chemistry properties of title complexes were determined by Elemental analysis, Molar conductance, UV absorption spectra, IR spectra and Thermogravimetric analysis. The title complexes exhibit characteristic red fluorescence of Eu3+. The effect of various substituent groups in ligands on the of title Eu3+ complexes is ordered: Cl > -Br > -OCH3 > -F > -CH3 > -H > -NO2, and [EuL6(NO3)2]NO3·EtOAc containing Cl possesses the strongest fluorescence intensity, so does fluorescence quantum yield. The electrochemical properties indicate that energy gap Eg and LUMO energy level are huge affected by substituent groups, and variation trends of LUMO energy level affected by diverse substituent groups are also different. The prepared title europium complexes have potential application prospects in the fields of photoelectric functional materials and life sciences.
Li, Dewei,Xiong, Suhao,Guo, Tiantong,Shu, Dehua,Xiao, Haihua,Li, Guizhi,Guo, Dongcai
p. 28 - 35
(2018/05/24)

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes
Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.
Wu, Yongqiang,Guo, Tiantong,Shu, Dehua,Zhang, Wu,Luan, Fangfei,Shi, Ling,Guo, Dongcai
p. 855 - 862
(2018/07/13)

The anti-invasive role of novel synthesized pyridazine hydrazide appended phenoxy acetic acid against neoplastic development targeting matrix metallo proteases
Neoplastic metastasis is a major process where tumor cells migrate from the primary tumor and colonize at other parts of our body to form secondary tumor. Cancer incidences are rising and novel anti-neoplastic compounds with new mechanism of actions are essential for preventing cancer related deaths. In the current examination, a novel series of pyridazine analogues 6a-l was synthesized and evaluated against metastatic neoplastic cells. Experimental data postulated compound 6j has potential cytotoxic efficacy with prolonged activity against various cancer cells, including A549, HepG2, A498, CaSki and SiHa cells. Moreover, compound 6j arrests the A549 migration and invasions markedly by counteracting matrix metalloproteinase (MMP)-2 and MMP-9 expressions. Also, compound 6j proved its potentiality against Dalton's solid lymphoma progression in-vivo by abridging MVD and MMP expressions. Compound 6j interacts with MMP-2 and MMP-9 by H- bond in-silico, thereby down regulates the MMPs action in tumourigenesis. Altogether, we concluded that compound 6j down regulates MMP-2 and MMP-9 and thereby impairs metastatic cancer cell migration and invasions which can be translated into a potent anti-neoplastic agent.
Eissa Mohammed, Yasser Hussein,Thirusangu, Prabhu,Zabiulla,Vigneshwaran,B.T, Prabhakar,Khanum, Shaukath Ara
p. 375 - 386
(2017/09/02)

CHEMCICAL COMPOUNDS
The invention is directed to substituted pyrrolidine derivatives. Specifically, the invention is directed to compounds according to Formula III: wherein A, B, L1, L2, L3, R1, R2, R3, R4, R5, R6, R9, R10, R30, Y1, Y2, z2, z4, z5, and z6 are as defined herein, and salts thereof. The compounds of the invention are inhibitors of the ATF4 pathway and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with activated unfolded protein response pathways, such as Alzheimer's disease, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, diabetes, Parkinson disease, Huntington's disease, Creutzfeldt-Jakob Disease, and related prion diseases, progressive supranuclear palsy, amyotrophic lateral sclerosis, myocardial infarction, cardiovascular disease, inflammation, fibrosis, chronic and acute diseases of the liver, chronic and acute diseases of the lung, chronic and acute diseases of the kidney, chronic traumatic encephalopathy (CTE), neurodegeneration, dementia, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting the ATF4 pathway and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
-
(2018/01/17)

CHEMICAL COMPOUNDS AS ATF4 PATHWAY INHIBITORS
The invention is directed to substituted piperidine derivatives. Specifically, the invention is directed to compounds according to Formula IIII: wherein A, B, X, Y, L1, L2, L3, R1, R2, R3, R4, R5, R6, R9, z2, z4, z5, and z6 are as defined herein, and salts thereof. The compounds of the invention are inhibitors of the ATF4 pathway and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with activated unfolded protein response pathways, such as Alzheimer's disease, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, diabetes, Parkinson disease, Huntington's disease, Creutzfeldt-Jakob Disease, and related prion diseases, progressive supranuclear palsy, amyotrophic lateral sclerosis, myocardial infarction, cardiovascular disease, inflammation, fibrosis, chronic and acute diseases of the liver, chronic and acute diseases of the lung, chronic and acute diseases of the kidney, chronic traumatic encephalopathy (CTE), neurodegeneration, dementia, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting the ATF4 pathway and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
-
(2018/01/19)

Herbicidal and fungistatic properties of fluorine analogs of phenoxyacetic herbicides
Aryloxy fluoroacetic acids 3a-3h – fluorine analogs of phenoxyacetic herbicides 2,4-D, MCPA, 2,4,5-T, and 4-CPA were efficiently synthesized in 29–88% yield, using appropriate phenols and either bromodifluoro- or bromofluoroacetic acid in the presence of sodium hydride as a base and in either dioxane or THF as solvents. Fluorine derivatives of 2,4-D (3a, 3b) show herbicidal activity against three weed species. Parent herbicides 2,4-D, MCPA, 2,4,5-T, 4-CPA, monofluorine derivatives of MCPA (3d) and 2,4,5-T (3f) show fungistatic activity against phytopatogenic fungi species Phytophtora cactorum.
Huras, Bogumi?a,Zakrzewski, Jerzy,Kie?czewska, Anna,Krawczyk, Maria
p. 76 - 81
(2017/09/25)

Synthesis and biological evaluation of aryloxyacetamide derivatives as neuroprotective agents
A series of new aryloxyacetamide derivatives 10a-s and 14a-m are designed and synthesized. Their protective activities against the glutamate-induced cell death were investigated in differentiated rat pheochromocytoma cells (PC12 cells). Most compounds exhibited neuroprotective effects, especially for 10m, 10r, 14b and 14c, which showed potential protection of PC12 cells at three doses (0.1, 1.0, 10 μM). MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 10m, 10r, 14b and 14c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke. Basic structure-activity relationships are also presented.
Zhong, Yan,Xu, Yi,Zhang, Ai-Xia,Li, Xiao-Feng,Xu, Zhao-Ying,Li, Ping,Wu, Bin
p. 2526 - 2530
(2016/07/07)

An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH2Cl2. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity. 2-(2-((1-Bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one, II-13, displayed high, broad-spectrum, and postemergent herbicidal activity at the dosage of 37.5-150 g ai/ha, nearly as potent as mesotrione against some weeds. Furthermore, II-13 showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that II-13 might have potential as a herbicide for weed control in maize and canola fields. II-13 is the first HPPD inhibitor showing good crop safety toward canola.
Wang, Da-Wei,Lin, Hong-Yan,He, Bo,Wu, Feng-Xu,Chen, Tao,Chen, Qiong,Yang, Wen-Chao,Yang, Guang-Fu
p. 8986 - 8993
(2016/12/09)

Degradation of organochlorinated pollutants in water by catalytic hydrodechlorination and photocatalysis
The degradation of chlorinated herbicides (MCPA and 2,4-D) and 4-chlorophenol (4-CP) by photocatalytic oxidation (PCO) and the combination of catalytic hydrodechlorination (HDC) and photocatalysis, at ambient conditions, has been studied. Commercial TiO2 (P25) and Pd/Al2O3 catalysts were used for PCO and HDC, respectively. MCPA and 2,4-D were transformed upon photo-oxidation to intermediate products and almost total mineralization was achieved. However, in the case of 4-CP, a conversion of only 82% of chloride formation and 87% TOC were obtained. In spite of the fact that the HDC reaction resulted in a total dechlorination of organochlorinated pollutants combined with an important decrease of the effluent ecotoxicity, the percentage of mineralization obtained in the combined process (HDC-PCO) was slightly lower than in the PCO treatment. Thus, the HDC-PCO process is not justified versus a single PCO treatment.
Diaz, Elena,Cebrian, Marina,Bahamonde, Ana,Faraldos, Marisol,Mohedano, Angel F.,Casas, Jose A.,Rodriguez, Juan J.
p. 168 - 174
(2016/03/25)

Synthesis and properties of coumarin derivatives and their terbium complexes
A series of coumarin derivatives obtained from salicylaldehyde and phenol were synthesized. Their corresponding terbium complexes were prepared and characterized by elemental analysis, EDTA titrations, molar conductivity, UVvis spectra, IR spectra, and thermal analysis. The luminescent properties and electrochemical properties of the terbium complexes were also investigated. The results showed that all the terbium complexes exhibited characteristic emissions of terbium ions. The introduction of electron-donating groups can improve the luminescent properties, decrease the HOMO and LUMO energy levels of the terbium complex, while electron-withdrawing groups can weaken the luminescent properties, and increase the HOMO and LUMO energy levels of terbium complex.
Meng, Defen,Xu, De,Li, Dong,Dai, Ming,Li, Guizhi,Guo, Dongcai
p. 5269 - 5280
(2016/06/01)

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate
(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.
Mo, Wenyan,Shi, Yanxia,He, Junbo,Li, Baoju,Peng, Hao,He, Hongwu
p. 183 - 187
(2016/02/10)

Discovery of 1,3-diethyl-7-methyl-8-(phenoxymethyl)-xanthine derivatives as novel adenosine A1and A2Areceptor antagonists
Based on a previous report that a series of 8-(phenoxymethyl)-xanthines may be promising leads for the design of A1adenosine receptor antagonists, selected novel and known 1,3-diethyl-7-methyl-8-(phenoxymethyl)-xanthine and 1,3,7-trimethyl-8-(phenoxymethyl)-xanthine analogs were synthesized and evaluated for their A1and A2Aadenosine receptor affinity. Generally, the study compounds exhibited affinity for both the A1and A2Aadenosine receptors. Replacement of the 1,3-dimethyl-substition with a 1,3-diethyl-substition pattern increased A1and A2Abinding affinity. Overall it was found that para-substitution on the phenoxymethyl side-chain of the 1,3-diethyl-xanthines decreased A1affinity except for the 4-Br analog (4f) exhibiting the best A1affinity in the submicromolar range. On the other hand A2Aaffinity for the 1,3-diethyl-xanthines were increased with para-substitution and the 4-OCH3(4b) analog showed the best A2Aaffinity with a Kivalue of 237?nM. The 1,3-diethyl-substituted analogs (4a, and 4f) behaved as A1adenosine receptor antagonists in GTP shift assays performed with rat whole brain membranes expressing A1adenosine receptors. This study concludes that para-substituted 1,3-diethyl-7-methyl-8-(phenoxymethyl)-xanthine analogs represent novel A1and A2Aadenosine receptor antagonists that are appropriate for the design of therapies for neurodegenerative disorders such as Parkinson's and Alzheimer's disease.
Harmse, Rozanne,van der Walt, Mietha M.,Petzer, Jacobus P.,Terre'Blanche, Gisella
supporting information
p. 5951 - 5955
(2016/12/03)

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates
A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.
Wang, Tao,Wang, Wei,Peng, Hao,He, Hongwu
p. 173 - 179
(2015/01/30)

1,3,4-Thiadiazol-2-amine Derivatives as Urotensin-II Receptor (UT) Antagonists
-
Lim, Chae Jo,Jang, Ju Young,Kim, Sung Hwan,Lee, Byung Ho,Oh, Kwang-Seok,Yi, Kyu Yang
p. 2549 - 2552
(2015/10/19)

Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus
In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.
Wu, Deyan,Mei, Hanbing,Tan, Ping,Lu, Weiqiang,Zhu, Jin,Wang, Wei,Huang, Jin,Li, Jian
supporting information
p. 4383 - 4387
(2015/06/22)

Synthesis, Characterization and Properties of Novel Coumarin Derivatives and Their Europium Complexes
Seven novel coumarin derivatives derived from salicylaldehyde and phenol were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their corresponding Eu(III) complexes having general formula EuL1-7(NO3)3·2H2O were successfully prepared and characterized by elemental analysis, EDTA titrimetric, molar conductivity, UV-Vis, FT-IR and thermal performance studies. The luminescence properties, fluorescence quantum yields and the electrochemical properties of the title complexes were investigated. The results showed that the title complexes exhibited characteristic emissions of europium ions and possessed relatively good fluorescence quantum yields. The luminescence intensity of the complex with bromine-substituted group is the strongest among all the title complexes. The introduction of electron-withdrawing groups can increase the luminescence properties and fluorescence quantum yields, decrease the HOMO and LUMO energy levels of the title europium complexes, but electron-withdrawing group conversely. And these title complexes may possibly be useful for studying in luminescent materials field.
Yan, Dong,Li, Dong,Cheng, Guang,Yang, Zehui,Shi, Ling,Guo, Dongcai
p. 849 - 859
(2015/08/24)

Synthesis and luminescence properties of pyrazolone derivatives and their terbium complexes
Seven novel pyrazolone derivatives were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their terbium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, UV/vis spectra, infrared spectra and molar conductivity, as well as thermal analysis. The fluorescence properties and fluorescence quantum yields of the complexes were investigated at room temperature. The results indicated that pyrazolone derivatives had good energy-transfer efficiency for the terbium ion. All the terbium complexes emitted green fluorescence characteristic of terbium ions, possessed strong fluorescence intensity, and showed relatively high fluorescence quantum yields. Cyclic voltammograms of the terbium complexes were studied and the highest occupied molecular orbital (HOMO) and lowest occupied molecular orbital (LUMO) energy levels of these complexes were estimated.
Xiao, Haihua,Jiang, Xi,Li, Dong,Wu, Limin,Zhang, Wu,Guo, Dongcai
p. 677 - 685
(2015/12/04)

Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA
Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods.
Joshi, Shrinivas D.,More, Uttam A.,Koli, Deepshikha,Kulkarni, Manoj S.,Nadagouda, Mallikarjuna N.,Aminabhavi, Tejraj M.
p. 151 - 167
(2015/03/30)

Catalyst-free photoredox addition-cyclisations: Exploitation of natural synergy between aryl acetic acids and maleimide
Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy. UVA photolyses of aryloxy-, arylthio- and arylamino-acetic acids with maleimide yield oxa-, thia- and aza-tricyclo pyrroledione derivatives in the absence of a photoredox catalyst (see scheme). An intriguing mechanism has been proposed and has been supported and supplemented by NMR monitoring experiments, DFT computations and UV/Vis and EPR spectroscopy.
Manley, David W.,Mills, Andrew,O'Rourke, Christopher,Slawin, Alexandra M. Z.,Walton, John C.
p. 5492 - 5500
(2014/05/20)

In silico and pharmacological screenings identify novel serine racemase inhibitors
d-Serine is a coagonist of the N-methyl-d-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.
Mori, Hisashi,Wada, Ryogo,Li, Jie,Ishimoto, Tetsuya,Mizuguchi, Mineyuki,Obita, Takayuki,Gouda, Hiroaki,Hirono, Shuichi,Toyooka, Naoki
p. 3732 - 3735
(2014/09/03)

Synthesis and fluorescence properties of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol derivatives and their terbium complexes
Eight novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol derivatives have been designed and synthesized, and their corresponding Tb3+ complexes were also prepared successfully. The fluorescence properties and fluorescence quantum yields of the target complexes were investigated, the results showed that the ligands were an efficient sensitizer for Tb3+ luminescence, and the target complexes exhibited characteristic fluorescence emissions of Tb3+ ion. The fluorescence intensity of the complex substituted by chlorine was stronger than that of other complexes. The substituents' nature has a great effect upon the electrochemical properties of the target complexes. The results showed that the introduction of the electron-withdrawing groups tended to decrease the oxidation potential and highest occupied molecular orbital energy levels of the target Tb3+ complexes; however, introduction of the electron-donating groups can increase the corresponding complexes' oxidation potential and highest occupied molecular orbital energy levels.
Zhang, Wu,Chai, Yuchao,Li, Kangyun,Chen, Yanwen,Yan, Dong,Guo, Dongcai
p. 1113 - 1122
(2015/02/19)

Synthesis, characterization and properties of 1,2,4-triazolo[3,4-b][1,3,4] thiadiazole derivatives and their europium complexes
Eight novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives and their corresponding Eu(III) complexes were synthesized and characterized. From the spectral studies it has been concluded that the title Eu(III) complexes display six coordination. The investigation of the luminescence properties of the title complexes showed that the ligands favor energy transfers to the emitting energy level of europium ions. The title Eu(III) complexes exhibited characteristic emissions of europium ions, and possessed strong luminescence intensities, good fluorescence quantum yields, and the highest fluorescence quantum yield is up to 0.522. Furthermore, the luminescence intensity of the complex with chlorine-substituted group is the strongest than that of other complexes. The exploration of the electrochemical properties of the title complexes shows that the introduction of electron-donating groups can increase the HOMO energy levels, LUMO energy levels and the oxidation potential of the complexes, however, the result of introduction of electron-withdrawing groups was just opposite.
Yan, Dong,Xiang, Yu,Li, Kangyun,Chen, Yanwen,Yang, Zehui,Guo, Dongcai
p. 487 - 495
(2014/07/21)

Design, synthesis and PASS assisted evaluation of novel 2-substituted benzimidazole derivatives as potent anthelimintics
Two series of compounds (AB and APB) bearing substituted phenoxy groups at 2-position of benzimidazole nucleus through amino or phenyleneamino were synthesized and evaluated through PASS software for predicting the activity spectrum of each compound. All compounds of both the series were predicted to have potent anthelmintic activity. The activity of each compound was evaluated experimentally at the concentrations of 0.1, 0.2 and 0.5% in terms of mortality time and paralysis time of the helminthes and was found to comply with the PASS predicted activity. In general, all compounds of APB series were more potent than those of AB series probably due to the additional hydrophobic interactions of the spacer phenyl ring in the APB series. The activity of all compounds was found to increase with increasing concentration. The compound with p-chlorophenoxy moiety was the most active from the APB series (mortality time 5.7±0.4 min and paralysis time 3.1±0.3 min) and equipotent to albendazole (mortality time 5.4±0.1 min and paralysis time 2.8±0.2 min) at concentration of 0.2%. The o-chlorophenoxy analogs in both the series were found to be the least active of all. Based on these results, a substituent capable of binding with the receptor through van der Waals and/or electronic interactions at 4-position of the phenoxy ring in the compound is suggested to increase binding interaction leading to potent anthelmintic activity.
Singh, Gurmeet,Bansal, Yogita,Bansal, Gulshan,Goel, Rajesh Kumar
p. 418 - 425
(2014/05/20)

Synthesis, Structure, and Properties of the 2-[5-(Aryloxyacetyl)-Amino-1,3,4-Thiadiazol-2-Ylthio] Propionate Derivatives
A series of novel 2-[5-(aryloxyacetyl)-amino-1,3,4-thiadiazol-2-ylthio] propionate derivatives were synthesized in high yield, and their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis, coupled with one selected single-crystal X-ray structure determination. The herbicidal activities of target compounds were assessed. The preliminary bioassay results showed that some compounds exhibited moderate to strong herbicidal symptoms in preemergence and postemergence tests. At 150 g/ha, S. tritici. show tolerance, while E. crus-galli L., E. Dahuricus, A. retroflexus, and C. glaucum L. were killed or severely injured. The activity of some compounds was comparable to the commercial herbicide 2,4-D. A suitable electron-withdrawing substituent at the 2-and/or 4-position of the phenyl ring was essential for high herbicidal activity. Moreover, the antifungal activities of the compounds have also been studied. The compounds were found to possess broad-spectrum antifungal activity.
Hu, Bing,Zhai, Yue-Yuan,Zhang, Ling,Zhang, You-Ming,Wei, Tai-Bao
p. 1337 - 1345
(2015/10/29)

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.
More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.
p. 199 - 218
(2014/01/06)

Design, synthesis and molecular docking of amide and urea derivatives as Escherichia coli PDHc-E1 inhibitors
By targeting the ThDP binding site of Escherichia coli PDHc-E1, two new 'open-chain' classes of E. coli PDHc-E1 inhibitors, amide and urea derivatives, were designed, synthesized, and evaluated. The amide derivatives of compound 6d, with 4-NO2 in the benzene ring, showed the most potent inhibition of E. coli PDHc-E1. The urea derivatives displayed more potent inhibitory activity than the corresponding amide derivatives with the same substituent. Molecular docking studies confirmed that the urea derivatives have more potency due to the two hydrogen bonds formed by two NH of urea with Glu522. The docking results also indicate it might help us to design more efficient PDHc-E1 inhibitors that could interact with Glu522.
He, Jun-Bo,Ren, Yan-Liang,Sun, Qiu-Shuang,You, Ge-Yun,Zhang, Li,Zou, Peng,Feng, Ling-Ling,Wan, Jian,He, Hong-Wu
p. 3180 - 3186
(2014/06/09)

Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors
Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.
Ozcan, Sevil,Kazi, Aslamuzzaman,Marsilio, Frank,Fang, Bin,Guida, Wayne C.,Koomen, John,Lawrence, Harshani R.,Sebti, Sa?d M.
p. 3783 - 3805
(2013/06/27)

PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS
Focused library synthesis and medicinal chemistry on an oxadiazole- isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring?s para-position and meta-pyridyl group at the B- ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer)
-
Page/Page column 57

(2012/10/08)

Synthesis and biological activity of 2-Aryloxyacetylamino-2-Deoxy-D- Glucoses
D-Glucosamine possesses extensive bioactivities including antibacterial, insecticidal and plant growth-regulating activities. A series of 2-aryloxyacetylamino-2-deoxy-D-glucoses have been synthesized by acylation of D-glucosamine with aryloxyacetyl chlorides and their plant growth-regulating activities were tested. The results show that these compounds bearing chlorine atom at para position of benzene ring have notable inhibiting activities against cotyledon rootage of cucumber which are comparable with that of 2,4-dichlorophenoxyacetic acid.
Han, Liang,Zhu, Qiong-Yan,Jia, Jian-Hong,Li, Yu-Jin,Gao, Jian-Rong
experimental part
p. 1223 - 1226
(2012/09/07)

Electrochemical reductive dechlorination of 2,4-dichlorophenoxyacetic acid using a palladium/nickel foam electrode
The electrochemical reductive dechlorination of 2,4-dichlorophenoxyacetic acid (2,4-D) in an aqueous solution was investigated at ambient temperature using a palladium/nickel foam (Pd/Ni foam) electrode in batch mode experiments. The catalytic electrode prepared using the standard chemical deposition method was further characterized using X-ray diffraction and scanning electron microscopy. It was observed that the reaction followed a pseudo-first-order kinetics model, the magnetic agitator-supported system could achieve 87% removal of 2,4-D within 4 h, which is 16% higher than the efficiency obtained under a nitrogen atmosphere. No organic intermediates other than phenoxyacetic (PA), o-chlorophenoxyacetic acid (o-CPA) and p-chlorophenoxyacetic acid (p-CPA) were observed to be generated during the reaction. The dechlorination efficiency depended on several factors including the current density, the palladium loading and the initial concentrations of the supporting NaCl electrolyte and the 2,4-D. The palladium loading and the NaCl concentration had a greater effect on the dechlorination kinetics of 2,4-D. Furthermore, the efficiencies of dechlorination and PA formation could be improved by optimizing the reaction system by modifying the ventilation conditions.
Zhu, Kairan,Baig, Shams Ali,Xu, Jiang,Sheng, Tiantian,Xu, Xinhua
experimental part
p. 389 - 396
(2012/06/01)

Synthesis and evaluation of antibacterial and antifungal activities of some novel 2,5-disubstituted-1,3,4-oxadiazoles
4-Chlorophenoxy acetic acid 2 was prepared by the condensation of phenol with monochloroacetic acid. Compound 2 was refluxed with ethanol in the presence of HCI gas yielding ethyl (4-chlorophenoxy) acetate 3. Compound 3 was refluxed with hydrazine hydrate in ethanol which produced 2-(4-chlorophenoxy) acetohydrazide 4. Compound 5a was synthesized by refluxing 2-(4-chlorophenoxy) acetohydrazide 4 with carbon disulfide and KOH in the presence of ethanol. Compound 5a on condensation with pbenzoquinone yielded 2-({4-[(4-chlorophenoxy) methyl]-1,3-4-oxadiazole-2-yl} sulfanyl) benzene-1,4-diol 5b. Oxadiazoles 6a-d were prepared by reacting substituted phenoxy acetic acids with 2-(4-chlorophenoxy) acetohydrazide 4 in the presence of POCI3. Further Schiff bases were synthesized by the reaction of substituted aldehydes with 2-(4-chlorophenoxy) acetohydrazide 4 in presence of ethanol. These Schiff bases on reaction with acetic anhyd gave the corresponding 3-acetyl-2,3-dihydro 1,3,4-oxadiazoles 7ad. Synthesized compounds were characterized on the basis of spectral and analytical data. All the compounds were screened for antimicrobial activity.
Joshi,Unale,Parkale,Nadagouda,Gadaginamath,Ashalata
p. 319 - 322
(2013/09/24)

Synthesis and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one
A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.
Wang, Wei,He, Hong-Wu,Zuo, Na,He, Hai-Feng,Peng, Hao,Tan, Xiao-Song
scheme or table
p. 7581 - 7587
(2012/10/08)