- Application of magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst in the synthesis of β-lactams containing amino groups
-
Herein we report the catalytic activity of magnetic Fe3O4 nanoparticles to promote the reduction of β-lactams containing nitroaryl groups to β-lactams containing aminoaryl groups in ethanol. The catalytic experimental conditions have
- Moslehi, Aleme,Zarei, Maaroof
-
-
Read Online
- Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors
-
Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.
- Xin, Weixiang,Li, Zezhong,Wang, Qing,Du, Jin,Zhu, Mingyan,Zhou, Huchen
-
-
- 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
-
supporting information
p. 233 - 247
(2020/03/27)
-
- 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)
-
- Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells
-
A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). In particular, compound 7a also exhibited strong antiproliferative activity against several stubborn cancer cells, including AsPC-1 cells (IC50 = 0.105 μM), BxPC-3 cells (IC50 = 0.090 μM), and MCF-7/ADR cells (IC50 = 0.59 μM). Additionally, compound 7a also showed great antitumor efficacy in vivo via aAsPC-1 cancer Xenograft mouse model. The preliminary mechanism study by Western blot analysis revealed that 7a repressed FAK phosphorylation in AsPC cancer cells. Taken together, the results indicate that compound 7a may serve as a promising preclinical candidate for treatment of stubborn cancers.
- Wang, Luhong,Ai, Min,Yu, Jiawen,Jin, Lingling,Wang, Changyuan,Liu, Zhihao,Shu, Xiaohong,Tang, Zeyao,Liu, Kexin,Luo, Hui,Guan, Wenshun,Sun, Xiuli,Ma, Xiaodong
-
p. 154 - 162
(2019/04/13)
-
- 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)
-
- Identification of highly potent BTK and JAK3 dual inhibitors with improved activity for the treatment of B-cell lymphoma
-
The BTK and JAK3 receptor tyrosine kinases are two validated and therapeutically amenable targets in the treatment of B-cell lymphomas. Here we report the identification of several classes of pyrimidine derivatives as potent BTK and JAK3 dual inhibitors.
- Ge, Yang,Wang, Changyuan,Song, Shijie,Huang, Jiaxin,Liu, Zhihao,Li, Yongming,Meng, Qiang,Zhang, Jianbin,Yao, Jihong,Liu, Kexin,Ma, Xiaodong,Sun, Xiuli
-
p. 1847 - 1857
(2017/12/04)
-
- 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
-
-
- Purine compounds, composition and application
-
The invention belongs to the technical field of medicine and relates to purine compounds, composition and an application of the composition. The compounds represented as a general formula (I) as well as all possible isomers, pharmaceutical salts or hydrates or the composition of the compounds are used for treating diseases caused by BTK (Bruton tyrosine kinase) and particularly used for treating diffuse large B cell lymphoma, follicular lymphoma or chronic lymphocytic leukemia.
- -
-
Paragraph 0106; 0107
(2017/07/04)
-
- Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism
-
Previously, we reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.
- Naik, Ravi,Ban, Hyun Seung,Jang, Kyusic,Kim, Inhyub,Xu, Xuezhen,Harmalkar, Dipesh,Shin, Seong-Ah,Kim, Minkyoung,Kim, Bo-Kyung,Park, Jaehyung,Ku, Bonsu,Oh, Sujin,Won, Misun,Lee, Kyeong
-
p. 8631 - 8646
(2017/11/03)
-
- Structural optimization of diphenylpyrimidine derivatives (DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B leukemia cell lines
-
A new series of diphenylpyrimidine derivatives (DPPYs) bearing various aniline side chains at the C-2 position of pyrimidine core were synthesized as potent BTK inhibitors. Most of these inhibitors displayed improved activity against B leukemia cell lines compared with lead compound spebrutinib. Subsequent studies showed that the peculiar inhibitor 7j, with IC50values of 10.5 μM against Ramos cells and 19.1 μM against Raji cells, also displayed slightly higher inhibitory ability than the novel agent ibrutinib. Moreover, compound 7j is not sensitive to normal cells PBMC, indicating low cell cytotoxicity. In addition, flow cytometry analysis indicated that 7j significantly induced the apoptosis of Ramos cells, and arrested the cell cycle at the G0/G1 phase. These explorations provided new clues to discover pyrimidine scaffold as more effective BTK inhibitors.
- Zhao, Dan,Huang, Shanshan,Qu, Menghua,Wang, Changyuan,Liu, Zhihao,Li, Zhen,Peng, Jinyong,Liu, Kexin,Li, Yanxia,Ma, Xiaodong,Shu, Xiaohong
-
p. 444 - 455
(2016/12/06)
-
- 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 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, 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)
-
- Finding new elicitors that induce resistance in rice to the white-backed planthopper Sogatella furcifera
-
Herein we report a new way to identify chemical elicitors that induce resistance in rice to herbivores. Using this method, by quantifying the induction of chemicals for GUS activity in a specific screening system that we established previously, 5 candidate elicitors were selected from the 29 designed and synthesized phenoxyalkanoic acid derivatives. Bioassays confirmed that these candidate elicitors could induce plant defense and then repel feeding of white-backed planthopper Sogatella furcifera.
- He, Xingrui,Yu, Zhaonan,Jiang, Shaojie,Zhang, Peizhi,Shang, Zhicai,Lou, Yonggen,Wu, Jun
-
supporting information
p. 5601 - 5603
(2015/11/17)
-
- 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)
-
- 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)
-
- 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)
-
- Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl) sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents
-
In this Letter, we report the structure-activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4- nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a-j) synthesized in good yields and chara
- Ranjith, P. Karuvalam,Rajeesh,Haridas, Karickal R.,Susanta, Nayak K.,Guru Row, Tayur N.,Rishikesan,Suchetha Kumari
-
p. 5228 - 5234
(2013/09/12)
-
- Selective, potent blockade of the IRE1 and ATF6 pathways by 4-phenylbutyric acid analogues
-
Background and Purpose 4-Phenylbutyric acid (4-PBA) is a chemical chaperone that eliminates the accumulation of unfolded proteins in the endoplasmic reticulum (ER). However, its chaperoning ability is often weak and unable to attenuate the unfolded protein response (UPR) in vitro or in vivo. To develop more potent chemical chaperones, we synthesized six analogues of 4-PBA and evaluated their pharmacological actions on the UPR. Experimental Approach NRK-52E cells were treated with ER stress inducers (tunicamycin or thapsigargin) in the presence of each of the 4-PBA analogues; the suppressive effects of these analogues on the UPR were assessed using selective indicators for individual UPR pathways. Key Results 2-POAA-OMe, 2-POAA-NO2 and 2-NOAA, but not others, suppressed the induction of ER stress markers GRP78 and CHOP. This suppressive effect was more potent than that of 4-PBA. Of the three major UPR branches, the IRE1 and ATF6 pathways were markedly blocked by these compounds, as indicated by suppression of XBP1 splicing, inhibition of UPRE and ERSE activation, and inhibition of JNK phosphorylation. Unexpectedly, however, these agents did not inhibit phosphorylation of PERK and eIF2α triggered by ER stress. These compounds dose-dependently inhibited the early activation of NF-κB in ER stress-exposed cells. 2-POAA-OMe and 2-POAA-NO2 also inhibited ER stress-induced phosphorylation of Akt. Conclusion and Implications The 4-PBA analogues 2-POAA-OMe, 2-POAA-NO2 and 2-NOAA strongly inhibited activation of the IRE1 and ATF6 pathways and downstream pathogenic targets, including NF-κB and Akt, in ER stress-exposed cells. These compounds may be useful for therapeutic intervention in ER stress-related pathological conditions.
- Zhang, Hui,Nakajima, Shotaro,Kato, Hironori,Gu, Liubao,Yoshitomi, Tatsuya,Nagai, Kaoru,Shinmori, Hideyuki,Kokubo, Susumu,Kitamura, Masanori
-
p. 822 - 834
(2013/10/22)
-
- 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)
-
- THERAPEUTICALLY ACTIVE COMPOUNDS FOR USE IN THE TREATMENT OF CANCER CHARACTERIZED AS HAVING AN IDH MUTATION
-
Compounds and compositions comprising compounds useful in the treatment of cancer are described herein. The compounds and compositions can be used to modulate an isocitrate dehydrogenase (IDH) mutant (e.g., IDHIm or IDH2m) having alpha hydroxyl neoactivity
- -
-
Page/Page column 112
(2011/06/26)
-
- Synthesis and biological evaluation of some novel 2-mercaptobenzothiazoles carrying 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole moieties
-
Several 2-mercaptobenzothiazole derivatives containing 1,3,4-oxadiazoles, 1,2,4-triazoles and 1,3,4-thiadiazoles at the second position were synthesized. Some of these synthesized compounds were evaluated for their in vivo analgesic, anti-inflammatory, acute toxicity and ulcerogenic actions. Some of the tested compounds showed significant analgesic and anti-inflammatory activities. Two of the compounds showed significant gastrointestinal protection compared to the standard drug diclofenac sodium. The compounds were also tested for their in vitro antimicrobial activity with most displaying selective activity against the Gram-negative bacteria Pseudomonas aeruginosa. In the present investigation the tested compounds did not possess antifungal activity.
- Azam, M. Afzal,Suresh, Bhojraj,Kalsi, Sandip S.,Antony, A. Shinesh
-
scheme or table
p. 114 - 122
(2011/06/09)
-
- Synthesis and antimicrobial activity of new 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles
-
A new series of 3-alkyl-6-aryloxy-1,2,4-triazolo [3,4-b] 1,3,4-thiadiazoles (4a-j) were synthesized by condensation of 3-alkyl-4-amino-5-mercapto-1,2,4- triazoles (2) with aryloxy acetic acids (3) in presence of POCI3. The structures of the newly synthesized compouds were assigned on the basis of IR, 1H NMR and Mass spectral data. All the new compounds were evaluated for their in-vitro antibacterial and antifungal activity.
- Revanasiddappa,Subrahmanyam,Satyanarayana
-
p. 195 - 196
(2013/09/23)
-
- Aza-Michael addition of acrylonitrile with 2-aryloxymethylbenzimidazole derivatives under microwave irradiation
-
A simple, rapid, and highly efficient method has been developed for the aza-Michael addition of acrylonitrile to 2-aryl-oxymethylbenzimidazole derivatives in the presence of anhydrous potassium carbonate under microwave irradiation. A series novel of 1-cyanoethyl-2-aryloxymethylbenzimidazole derivatives have been prepared and characterised by 1H NMR, 13C NMR, IR spectra and elemental analysis.
- Wei, Tai-Bao,Hua, Mao-Tang,Shi, Hai-Xiong,Liu, Yong,Zhang, You-Ming
-
scheme or table
p. 452 - 454
(2010/12/24)
-
- FUNCTIONALIZED PHENOLIC COMPOUNDS AND POLYMERS THEREFROM
-
The present invention relates to compounds of formula I, which are functionalized phenolic compounds, and polymers formed from the same. Ar—[O—(X)p—R′]q??I Polymers formed from the functionalized phenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.
- -
-
Page/Page column 34
(2009/07/17)
-
- Antimalarial activity enhancement in hydroxymethylcarbonyl (HMC) isostere-based dipeptidomimetics targeting malarial aspartic protease plasmepsin
-
Plasmepsin (Plm) is a potential target for new antimalarial drugs, but most reported Plm inhibitors have relatively low antimalarial activities. We synthesized a series of dipeptide-type HIV protease inhibitors, which contain an allophenylnorstatine-dimethylthioproline scaffold to exhibit potent inhibitory activities against Plm II. Their activities against Plasmodium falciparum in the infected erythrocyte assay were largely different from those against the target enzyme. To improve the antimalarial activity of peptidomimetic Plm inhibitors, we attached substituents on a structure of the highly potent Plm inhibitor KNI-10006. Among the derivatives, we identified alkylamino compounds such as 44 (KNI-10283) and 47 (KNI-10538) with more than 15-fold enhanced antimalarial activity, to the sub-micromolar level, maintaining their potent Plm II inhibitory activity and low cytotoxicity. These results suggest that auxiliary substituents on a specific basic group contribute to deliver the inhibitors to the target Plm.
- Hidaka, Koushi,Kimura, Tooru,Ruben, Adam J.,Uemura, Tsuyoshi,Kamiya, Mami,Kiso, Aiko,Okamoto, Tetsuya,Tsuchiya, Yumi,Hayashi, Yoshio,Freire, Ernesto,Kiso, Yoshiaki
-
scheme or table
p. 10049 - 10060
(2009/04/07)
-
- Synthesis and anti-inflammatory activity of 2-aryloxy methyl oxazolines
-
A series of potential biologically active 2-aryloxy methyl oxazolines 3a-n have been synthesized from substituted hydroxybenzenes 1a-n with good chemical yield. The compounds 3a-n were screened for their anti-inflammatory, ulcerogenic, cyclooxygenase activities and also for their acute toxicity. The potency of the compounds was compared with that of the standard drugs, aspirin and phenyl butazone. The outcome indicates that compounds 3b (48.2%), 3h (48.5%) and 3l (46.5%) offered significant anti-inflammatory activity with low ulcerogenic activity than the standard drugs.
- Khanum, Shaukath Ara,Khanum, Noor Fatima,Shashikanth
-
body text
p. 4597 - 4601
(2009/04/06)
-
- 2- [ (2-SUBSTITUTED) -IND0LIZIN-3-YL] -2-OXO-ACETAMIDE DERIVATIVES AS ANTIFUNGAL AGENTS
-
The invention provides compounds of formula (I), and pharmaceutically acceptable salts thereof wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. These compounds are useful in the manufacture of medicaments for use in the prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
- -
-
Page/Page column 116
(2008/12/05)
-
- (Aryloxyacetylamino)benzoic acid analogues: A new class of hypoxia-inducible factor-1 inhibitors
-
Structural modification of a compound discovered during screening using an HRE-dependent reporter assay has revealed a novel class of HIF-1 inhibitors, which potently inhibit the HIF-1α protein accumulation and its target gene expression under hypoxic conditions in human hepatocellular carcinoma Hep3B cells.
- Lee, Kyeong,Lee, Jeong Hyung,Boovanahalli, Shanthaveerappa K.,Jin, Yinglan,Lee, Mijeoung,Jin, Xuejun,Kim, Jin Hwan,Hong, Young-Soo,Lee, Jung Joon
-
p. 1675 - 1684
(2008/02/01)
-
- Functionalized drugs and polymers derived therefrom
-
Compounds selected from: where DRUG-OH, DRUG-COOH and DRUG-NH2 are biologically active compounds; each X is independently selected from —CH2COO— (glycolic acid moiety), —CH(CH3)COO— (lactic acid moiety), —CH2CH2OCH2COO— (dioxanone moiety), —CH2CH2CH2CH2CH2COO— (caprolactone moiety), —(CH2)yCOO—, where y is 2-4 or 6-24 and —(CH2CH2O)zCH2COO—, where z is 2-24; each Y is independently selected from —COCH2O— (glycolic ester moiety), —COCH(CH3)O— (lactic ester moiety), —COCH2OCH2CH2O— (dioxanone ester moiety), —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety), —CO(CH2)mO—, where m is 2-4 or 6-24 and —COCH2O(CH2CH2O)n— where n is between 2-24; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; and p is 1-6. Multi-functional compounds and drug dimers, oligomers and polymers are also disclosed.
- -
-
Page/Page column 21
(2008/06/13)
-
- A rapid and high-yield synthesis of aryloxyacetic acid in one pot under microwave irradiation and phase transfer catalysis conditions
-
A series of aryloxyacetic acid 3a-h has been synthesized in one pot under microwave irradiation and phase transfer catalysis conditions. By the optimization of the reaction condition, a rapid, high-yield and efficient method for the preparation of aryloxyacetic acid is reported.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
-
p. 1312 - 1314
(2007/10/03)
-
- Synthesis of Aryloxyacetic Acids, Esters, and Hydrazides Assisted by Microwave Irradiation
-
Under microwave irradiation on clay a series of transformations of a number of phenols into their aryloxyacetic acids 3 and then their methyl esters 4 and hydrazides 5 has been achieved efficiently in good yields.
- Hamid, Hamida M. Abdel,Ramadan, El Sayed,Hagar, Mohamed,El Ashry, El Sayed H.
-
p. 377 - 382
(2007/10/03)
-
- Synthesis of potent and selective inhibitors against the proliferation of human coronary artery smooth muscle cells.
-
A series of diarylamide urea derivatives were synthesized and evaluated for their inhibitory activities against human coronary artery smooth muscle cells (SMCs) and human coronary artery endothelial cells (ECs). Compound 2h was much superior to Tranilast, in terms of both the potency of its inhibitory activity toward the proliferation of SMCs and the cell selectivity.
- Ogita, Haruhisa,Isobe, Yoshiaki,Takaku, Haruo,Sekine, Rena,Goto, Yuso,Misawa, Satoru,Hayashi, Hideya
-
p. 117 - 121
(2007/10/03)
-
- Synthesis of analogs of juvenile hormons proceeding from phenol derivatives
-
New potential juvenoids, esters of alkenoic and alkadienoic acids with phenoxy-and phenoxy-phenoxyethanol were synthesized, and also esters of phenoxyacetic acid with alkenols amd alkadienols.
- Yamansarova,Kukovinets,Kukovinets,Zainullin,Galin,Kunakova,Zorin,Tolstikov
-
p. 246 - 255
(2007/10/03)
-
- Kinetics and mechanism of thermal gas-phase elimination of 2-aryloxyacetic acid
-
Rates of thermal gas-phase elimination of eleven 2-aryloxyacetic acid have been measured over a 45°C temperature range for each compound. Hammett correlation of the present kinetic data with the literature σ0 values of the given substituents gave a reaction ρ constant of 0.69 at 600 K; this is more than that for the gas-phase elimination parameter of 2-aryloxypropanoic acid (ρ = 0.26) and consistent with a transition state with some charge separation, suggesting a partial formation of carbocation. The implications of this observation for the thermal gas-phase elimination of α-aryloxycarboxylic acids are considered.
- Al-Awadi, Nouria A.,Kumar, Ajith,Chuchani, Gabriel,Herize, Armando
-
p. 612 - 616
(2007/10/03)
-
- Synthesis of 1,1,1-trichloro-2,2-bis-(carboxymethoxyaryl)ethanes as potential antimicrobial and insecticidal agents
-
Some new 1,1,1-trichloro-2,2-bis-(carboxymethoxyaryl)-ethanes 2a-t have been synthesised by the treating aryloxyacetic acid (two moles) with chloral hydrate (1 mole) in the presence of catalytic amount of conc. sulphuric acid. The aryloxyacetic acid are prepared by the reaction of substituted phenols with chloroacetic acid in the presence of aq. sodium hydroxide. The antimicrobial activity of these compounds have been assayed against various Gram+ve, Gram-ve bacteria and fungi. The constitution of the products have been elucidated by IR, 1H NMR and mass spectral data and elemental analyses.
- Purohit,Shah
-
p. 618 - 622
(2007/10/03)
-
- Syntheses of HIV-protease inhibitors having a peptide moiety which binds to GP120
-
Some HIV-protease inhibitor derivatives having an N- carbomethoxycarbonyl-prolyl-phenylalanine benzyl ester (CPF) moiety as a binding site to gp120 were designed and synthesized. Almost all the compounds bearing CPF on the phenoxyacetyl group showed protease-inhibitory activity. Compounds 25a and 25b, which have the CPF moiety at the ortho- and meta- positions of the phenoxyacetyl group, respectively, had anti-HIV activity, although the others showed only protease-inhibitory activity. These results suggest that 25b binds to gp120 and inhibits HIV protease.
- Asagarasu, Akira,Uchiyama, Taketo,Achiwa, Kazuo
-
p. 697 - 703
(2007/10/03)
-
- Synthesis of dipeptide-type human immunodeficiency virus (HIV) protease inhibitors with a binding unit to GP120
-
Some dipeptide-type human immunodeficiency virus (HIV) protease inhibitors derived from KNI-102, with a N-carbomethoxycarbonylprolyl- phenylalanine benzyl ester (CPF) moiety as a binding site to gp120, were synthesized. Compounds 11a showed 7 - 100 times higher HIV protease- inhibitory activity (11a; IC50 = 0.90 μg/ml, 1.1 μM) than the standard compound 3 or 4 (3; IC50 = 3.7 μg/ml, 7.7 μM, 4; IC50 = 75 μg/ml, 155 μM). Generally, the compounds substituted at the o-position of the phenoxyacetyl group 7a, 11a, 16a and 21a showed several times higher inhibitory activity than 3.
- Asagarasu, Akira,Takayanagi, Nao,Achiwa, Kazuo
-
p. 867 - 870
(2007/10/03)
-
- Juvenile hormone like substances: Part XI - Synthesis and biological activities of some juvenile hormone a alogues containing hydroxamate feature
-
A large number of juvenile hormone analogues (3 to 9) containing hydroxamate function have been synthesized. Preliminary biological screening investigations on one representative, (2,5-dioxo-3-aza-4-oxa-7-methyloctanyl)oxybenzene (3a) reveal a positive juvenile hormonal activity and chemosterilizing effect against potato tuber moth Phthorimaea opercuiella.
- Mahajan,Pai, Yogender,Anand, Shalu
-
p. 333 - 338
(2007/10/03)
-
- Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides
-
A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the CHRC/5 cell line.Among them the acridone derivatives were the most potent.A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain.Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone.On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy-9-oxo-N-phenyl>-4-acridinecarboxamide (84) has been selected for further development.
- Dodic, Nerina,Dumaitre, Bernard,Daugan, Alain,Pianetti, Pascal
-
p. 2418 - 2426
(2007/10/02)
-
- POLYMER SUPPORTED REAGENTS: USE OF ANION EXCHANGE RESIN IN THE SYNTHESIS OF ARYLOXY ACETIC ACIDS
-
Phenoxides supported on Amberlite IRA 400 on reaction with sodium salt of chloroacetic acid gave corresponding aryloxy acetic acid in high yields.Interestingly nitrophenols, 4-hydroxy coumarin and p-hydroxy ethylbenzoate gave excellent yields of the product.
- Deshmukh, J. G.,Jagdale, M. H.,Mane, R. B.,Salunkhe, M. M.
-
p. 479 - 484
(2007/10/02)
-
- Design, Synthesis, and Testing of Potential Antisickling Agents. 4. Structure-Activity Relationships of Benzyloxy and Phenoxy Acids
-
In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation.Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains.We have also found a halogenated aromatic malonic acid derivative to be quite active.Compounds reported in this paper are compared with other antigelling agents studied in our laboratory.Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function.
- Abraham, D. J.,Kennedy, P. E.,Mehanna, A. S.,Patwa, D. C.,Williams, F. L.
-
p. 967 - 978
(2007/10/02)
-
- Applicability of Hammett Equation to Insulated Systems - Kinetics of Alkaline Hydrolysis of meta- and para-Substituted Methyl Phenoxyacatates
-
The kinetics of alkaline hydrolysis of some meta- and para-substituted methyl phenoxyacetates have been determined in 85percent (wt/wt) methanol-water at 10 deg C, 15 deg C, and 20 deg C.The activation parameters have been evaluated from Arrhenius plots and the isokinetic temperature has been analysed.The applicability of Hammett equation to the above reaction has been discussed.The interesting behaviour of halogeno substituents is also discussed.
- Gurumurthy, R.,Balakrishnan, N.
-
p. 154 - 156
(2007/10/02)
-
