- Small molecule compound and application and composition thereof
-
The invention discloses a small molecule compound and application and a composition thereof, and the application of the small molecule compound is specifically as follows: 4-((2-(4-(tert-butyl)phenoxy)acetyl)glycyl)phenylbenzo[d] [1,3]dioxane-5-carboxylic ester, or pharmaceutically, healthcare or food acceptable salt or ester or derivative thereof, or a mixture thereof for preparing substances for treating tumors, inhibiting tumor cell growth and/or inducing tumor cell apoptosis, and the composition contains: (1) a compound 4-((2-(4-(tert-butyl)phenoxy)acetyl)glycyl)phenylbenzo [d][1, 3]dioxane-5-carboxylic acid esters, or pharmaceutically, healthcare or food acceptable salts or esters or derivatives thereof, or mixtures thereof; (2) an apoptosis-causing drug; and (3) a carrier or excipient acceptable in pharmacy, health care science or food science.
- -
-
-
- Effective removal of calcium and magnesium sulfates from wastewater in the rare earth industry
-
The wastewater discharged from the rare earth (RE) industry generally contains a high level of calcium and magnesium sulfates, which confers permanent hardness and causes difficulties in recycling this wastewater. In this study, the alkyl phenoxy acetic acid derivatives including 4-methyl phenoxy acetic acid (M-POAA), 4-tert-butyl phenoxy acetic acid (B-POAA) and 4-tert-octyl phenoxy acetic acid (O-POAA), were synthesized via the Williamson reaction and characterized by nuclear magnetic resonance (NMR), infrared (IR), and ultra-violet (UV) spectroscopy, as well as elemental analysis and X-ray diffraction (XRD). Synthesis of the POAAs were simple and green, and the raw materials used for their production are widely available and low-cost. The potential for removal of Ca and Mg sulfates from industrial wastewater using POAAs as the organic precipitants was assessed. The total precipitation efficiencies of Ca and Mg from wastewater with the use of POAAs increased with the following order: M-POAA -1, respectively. The O-POAA could be regenerated five times without any significant change in its structure and precipitation performance. Thus, the use of the novel precipitants is a prospective alternative to the conventional processes for softening wastewater.
- Wang, Yanliang,Guo, Xiangguang,Bai, Yan,Sun, Xiaoqi
-
p. 33922 - 33930
(2019/11/11)
-
- 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)
-
- Synthesis, structure and coordination properties of novel bifunctional carboxylic derivatives of 1,3-alternate tetrathiacalix[4]arene
-
New bifunctional derivatives of 1,3-alternate tetrathiacalix[4]arene decorated with carboxylic, ester, hydrazide and/or hydrazone groups have been synthesized with good yields using the tetrathiacalix[4]arene derivatives with incorporated pairs of carboxylic and ester groups as versatile building blocks. The structural peculiarities of the obtained bifunctional compounds have been investigated by means of X-ray analysis, IR and NMR spectroscopy. The recognition ability of the synthesized macrocycles towards some alkali, alkali-earth and transition metal ions has been investigated applying a solvent extraction method. The results showed that the structure of a calix[4]arene platform as well as the nature of functional substitutes located on opposite sides of the macrocycle are critical for the coordination properties of the synthesized compounds.
- Podyachev, Sergey N.,Gimazetdinova, Gulnaz Sh.,Gubaidullin, Aidar T.,Syakaev, Victor V.,Sudakova, Svetlana N.,Gabidullin, Bulat M.,Ivanov, Vladimir T.,Gogolashvili, Edward L.,Konovalov, Alexander I.
-
p. 19531 - 19544
(2016/02/27)
-
- 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)
-
- 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.
-
supporting information
p. 5492 - 5500
(2014/05/20)
-
- Direct C-F bond formation using photoredox catalysis
-
We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the 3MLCT (triplet metal-to-ligand charge transfer) state of Ru(bpy)32+ to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.
- Rueda-Becerril, Montserrat,Mahe, Olivier,Drouin, Myriam,Majewski, Marek B.,West, Julian G.,Wolf, Michael O.,Sammis, Glenn M.,Paquin, Jean-Francois
-
supporting information
p. 2637 - 2641
(2014/03/21)
-
- 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.
-
supporting information
p. 3783 - 3805
(2013/06/27)
-
- Discovery of potent transient receptor potential vanilloid 1 antagonists: Design and synthesis of phenoxyacetamide derivatives
-
We aimed to discover a novel type of transient receptor potential vanilloid 1 (TRPV1) antagonist because such antagonists are possible drug candidates for treating various disorders. We modified the structure of hit compound 7 (human TRPV1 IC50 = 411 nM) and converted its pyrrolidino group to a (hydroxyethyl)methylamino group, which substantially improved inhibitory activity (15d; human TRPV1 IC50 = 33 nM). In addition, 15d ameliorated bladder overactivity in rats in vivo.
- Takahashi, Eiki,Hirano, Noriyuki,Nagahara, Takashi,Yoshikawa, Satoru,Momen, Shinobu,Yokokawa, Hiroshi,Hayashi, Ryoji
-
p. 3154 - 3156
(2013/06/26)
-
- Highly selective and efficient extraction of two Pb2+ ions with a p-tert-butylcalix[6]arene hexacarboxylic acid ligand: An allosteric effect in extraction
-
Solvent extraction behavior of p-tert-butylcalix[6]arene hexacarboxylic acid towards Pb2+ and other divalent transition metal ions has been studied to investigate the selectivity, extraction mechanism, stoichiometry of complexation and composition of the complex in the organic phase. Extractability and selectivity of the cyclic ligand were analyzed in comparison with the acyclic analog. The macrocyclic effect was genuinely operative and the size-match effect was the governing factor for cation selectivity. Accordingly, the cyclic ligand selectively extracted the Pb2+ ion in a pH range fairly more acidic than the acyclic ligand. The cations were extracted by ion exchange mechanism, and the electroneutral complexes were resulted by the exchange of two protons for a divalent cation. A molecule of p-tert-butyl calix[6]arene hexacarboxylic acid ligand extracted two Pb2+ ions. One Pb2+ was extracted due to the size-fit effect inside the hydrophilic cavity of calix[6]arene composed by phenoxy and carbonyl oxygen atoms. The macrocyclic ring inversion was obstructed due to guest encapsulation, and the encapsulated Pb2+ ion acted as a template for aggregation of the carboxyl groups. This binding event caused a positive allosteric effect and led to the extraction of the second Pb2+ ion at the aggregated functional group site.
- Adhikari, Birendra Babu,Gurung, Manju,Chetry, Anup Basnet,Kawakita, Hidetaka,Ohto, Keisuke
-
p. 25950 - 25959
(2013/12/04)
-
- Photo-fluorodecarboxylation of 2-aryloxy and 2-aryl carboxylic acids
-
Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron-poor 2-aryloxy and 2-aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single-electron transfer. Copyright
- Leung, Joe C. T.,Chatalova-Sazepin, Claire,West, Julian G.,Rueda-Becerril, Montserrat,Paquin, Jean-Fran?ois,Sammis, Glenn M.
-
p. 10804 - 10807
(2013/01/15)
-
- Discovery of a novel series of benzimidazole derivatives as diacylglycerol acyltransferase inhibitors
-
A novel series of benzimidazole derivatives was prepared and evaluated for their diacylglycerol acyltransferase (DGAT) inhibitory activity using microsome from rat liver. Among the newly synthesized compounds, furfurylamine containing benzimidazole carboxamide 10j showed the most potent DGAT inhibitory effect (IC50= 4.4 μM) and inhibited triglyceride formation in HepG2 cells. Furthermore, compound 10j reduced body weight gain of Institute of Cancer Research mice on a high-fat diet and decreased levels of total triglyceride, total cholesterol, and LDL-cholesterol in the blood accompanied with a significant increase in HDL-cholesterol level.
- Lee, Kyeong,Goo, Ja-Il,Jung, Hwa Young,Kim, Minkyoung,Boovanahalli, Shanthaveerappa K.,Park, Hye Ran,Kim, Mun-Ock,Kim, Dong-Hyun,Lee, Hyun Sun,Choi, Yongseok
-
p. 7456 - 7460
(2013/02/22)
-
- 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 61
(2012/10/08)
-
- 1,3-diamido-calix[4]arene conjugates of amino acids: Recognition of -COOH side chain present in amino acids, peptides, and proteins by experimental and computational studies
-
Lower rim 1,3-diamido conjugates of calix[4]arene have been synthesized and characterized, and the structures of some of these have been established by single crystal XRD. The amido-calix conjugates possessing a terminal -COOH moiety have been shown to exhibit recognition toward guest molecules possessing -COOH moiety, viz., Asp, Glu, and reduced and oxidized glutathione (GSH, GSSG), by switch-on fluorescence in aqueous acetonitrile and methanol solutions when compared to the control molecules via forming a 1:1 complex. The complex formed has been shown by mass spectrometry, and the structural features of the complexes were derived on the basis of DFT computations. The association constants observed for the recognition of Asp/Glu by Phe-calix conjugate, viz., 532/676 M-1, are higher than that reported for the recognition of Val, Leu, Phe, His, and Trp (16-63 M-1) by a water-soluble calixarene (Arena, G., et al. Tetrahedron Lett. 1999, 40, 1597). For this recognition, there should be a free -COOH moiety from the guest molecule. AFM, SEM, and DLS data exhibited spherical particles with a hundred-fold reduction in the size of the complexes when compared to the particles of the precursors. These spherical particles have been computationally modeled to possess hexameric species reminiscent of the hexameric micellar structures shown for a Ag+ complex of a calix[6]arene reported in the literature (Houmadi, S., et al. Langmuir 2007, 23, 4849). Both AFM and TEM studies demonstrated the formation of nanospheres in the case of GSH-capped Ag nanoparticles in interaction with the amido-calix conjugate that possesses terminal -COOH moiety. The AFM studies demonstrated in this paper have been very well applied to albumin proteins to differentiate the aggregational behavior and nanostructural features exhibited by the complexes of proteins from those of the uncomplexed ones. To our knowledge, this is the first report wherein a amido-calix[4]arene conjugate and its amino acid/peptide/protein complexes have been differentiated on the basis of spectroscopy and microscopy studies followed by species modeling by computations.
- Acharya, Amitabha,Ramanujam, Balaji,Chinta, Jugun Prakash,Rao, Chebrolu P.
-
scheme or table
p. 127 - 137
(2011/03/22)
-
- Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1α inhibitors
-
A series of boron-containing phenoxyacetanilide derivatives 8a-f, 9a-f, 15, and 16 were synthesized as hypoxia-inducible factor (HIF)-1α inhibitors. Among the compounds synthesized, carboranylphenoxyacetanilide 16 (GN26361) was found to be a potent inhibitor against HIF-1α accumulation under hypoxic conditions and inhibited the hypoxia-induced HIF-1 transcriptional activity in HeLa cells (IC50 = 0.74 μM). Compound 16 suppressed hypoxia-induced HIF-1α accumulation and vascular endothelial growth factor mRNA expression in a concentration-dependent manner without affecting the expression of HIF-1α mRNA.
- Shimizu, Kazuki,Maruyama, Minako,Yasui, Yuka,Minegishi, Hidemitsu,Ban, Hyun Seung,Nakamura, Hiroyuki
-
scheme or table
p. 1453 - 1456
(2010/07/06)
-
- Benzothiazole appended lower rim 1,3-di-amido-derivative of calix[4]arene: Synthesis, structure, receptor properties towards Cu2+, iodide recognition and computational modeling
-
A new molecular fluorescent sensor (L) for Cu2+ has been synthesized by derivatizing the lower rim of calix[4]arene with benzothiazole moiety, through amide linkage to result in 1,3-di-derivative. The receptor molecule, L exhibited fluorescence quenching towards Cu2+ among eleven divalent ions, viz., Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg 2+, Ca2+, Mg2+ and Pb2+, studied. The 1:1 stoichiometry of the complex formed between L and Cu2+ has been demonstrated by electronic absorption and ESI-MS. The role of calix[4]arene for the selective sensing of Cu2+ has been established by comparing the data with that obtained for an appropriate control molecule. The minimum concentration at which L can detect Cu2+ has been found to be 403 ppb. The computations carried out at DFT level have provided the coordination and structural features of the Cu2+ complex of L as species of recognition. The Cu2+ complex thus formed recognizes iodide by bringing change in the color, among the 14 anions studied.
- Joseph, Roymon,Chinta, Jugun Prakash,Rao, Chebrolu P.
-
experimental part
p. 2833 - 2839
(2011/03/01)
-
- Fluorescence switch-on sensor for Cu2+ by an amide linked lower rim 1,3-bis(2-picolyl)amine derivative of calix[4]arene in aqueous methanol
-
A highly selective fluorescence switch on sensor, L for detecting Cu2+ has been synthesized by introducing a bis-(2-picolyl)amine moiety at the lower rim of a calix[4]arene platform via amide linkage. Binding properties of L toward ten different biologically relevant Mn+ ions have been studied by fluorescence and absorption spectroscopy in methanol and aqueous methanol. L was found to detect Cu2+ selectively down to a concentration of 196 and 341 ppb, respectively, in methanol and 1:1 aqueous methanol even in the presence of other metal ions. The composition of the complex has been found to be 1:1 based on the Job plot and is further confirmed by ESI MS. The role of calix[4]arene platform as well as the pre-organized binding core in the selective recognition of Cu2+ has been demonstrated by studying appropriate reference molecules. The possible modes of binding of L with Cu2+ have been modeled by computational calculations. L and its Cu2+ complex could very well be differentiated based on the nano-structural features observed in SEM and AFM.
- Joseph, Roymon,Ramanujam, Balaji,Acharya, Amitabha,Rao, Chebrolu P.
-
scheme or table
p. 2735 - 2739
(2009/09/06)
-
- Lower rim 1,3-di{bis(2-picolyl)}amide derivative of calix[4]arene (L) as ratiometric primary sensor toward Ag+ and the complex of Ag + as secondary sensor toward cys: Experimental, computational, and microscopy studies and INHIBIT logic gate properties of L
-
(Figure Presented) Astructurally characterized lower rim 1,3-di{bis(2-picolyl)}amide derivative of calix[4]arene (L) exhibits high selectivity toward Ag+ by forming a 1:1 complex, among nine other biologically important metal ions, viz., Na+, K+, Mg 2+, Ca2+, Mn2+, Fe2+, Co 2+, Ni2+, and Zn2+, as studied by fluorescence, absorption, and 1H NMR spectroscopy. The 1:1 complex formed between L and Ag+ has been further proven on the basis of ESI mass spectrometry and has been shown to have an association constant, Ka, of 11117 ± 190 M-1 based on fluorescence data. L acts as a primary ratiometric sensor toward Ag+ by switch-on fluorescence and exhibits a lowest detectable concentration of 450 ppb. DFT computational studies carried out in mimicking the formation of a 1:1 complex between L and Ag + resulted in a tetrahedral complex wherein the nitrogens of all four pyridyl moieties present on both arms are being coordinated. Whereas these pyridyls are located farther apart in the crystal structure, appropriate dihedral changes are induced in the arms in the presence of silver ion in order to form a coordination complex. Even the nanostructural features obtained in TEM clearly differentiates L from its Ag+ complex. The in situ prepared silver complex of L detects Cys ratiometrically among the naturally occurring amino acids to a lowest concentration of 514 ppb by releasing L from the complex followed by formation of the cysteine complex of Ag+. These were demonstrated on the basis of emission, absorption, 1H NMR, and ESI mass spectra. The INH logic gate has also been generated by choosing Ag + and Cys as input and by monitoring the output signal at 445 nm that originates from the excimer emission of L in the presence of Ag+. Thus L is a potential primary sensor toward Ag+and is a secondary sensor toward Cys. 2009 American Chemical Society.
- Joseph, Roymon,Ramanujam, Balaji,Acharya, Amitabha,Rao, Chebrolu P.
-
scheme or table
p. 8181 - 8190
(2010/02/28)
-
- Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid derivatives
-
A series of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid (norfloxacin) derivatives were prepared according to the principle of combinating bioactive substructures and tested for their activities against five plant pathogenic bacteria and three fungi in vitro. The preliminary bioassays indicated that almost all synthesized target compounds retained the antibacterial activities of norfloxacin and had some antifungal activities as carboxylic acid amide compounds. The activities of compounds 1 and 22 against Xanthomonas oryzae were better than norfloxacin and all tested compounds had better antibacterial activities as compared to the agricultural streptomycin sulfate (a commercial bactericide) against X. oryzae, Xanthomonas axonopodis and Erwinia aroideae. Additionally, compounds 2 and 20 displayed good antifungal activities against Rhizoctonia solani and their inhibition of growth reached 83% and 94% respectively at the concentration of 200 mg/L.
- Yu, Zhiyi,Shi, Guanying,Sun, Qiu,Jin, Hong,Teng, Yun,Tao, Ke,Zhou, Guoping,Liu, Wei,Wen, Fang,Hou, Taiping
-
scheme or table
p. 4726 - 4733
(2010/01/06)
-
- The influence of isomerism on the self-assembly behavior and complexation property of 1,3-alternate tetraaminopyridyl-thiacalix[4]arene derivatives
-
A series of 1,3-alternate conformation thiacalix[4]arenes containing different isomeric aminopyridyl pendent arms have been synthesized. It was found that their self-assembly behaviors and complexation properties strongly depended on the structures of aminopyridyl pendent arms. The crystal structures demonstrate that tetra(meta-aminopyridyl)-thiacalix[4]arene motif is capable of forming intramolecular hydrogen bondings between the sp2 nitrogen donors in the meta position of the aminopyridyl groups and the facing amide N-H of the adjacent aminopyridyl groups, and self-assembles via C-H?O weak hydrogen bondings and C-H?π interaction to generate a double stranded rectilineal networks. By contrast, in the case of tetra(para-aminopyridyl)-thiacalix[4]arene, the presence of para-aminopyridyl units enables the formation of N-H?N strong hydrogen bondings between the individual molecules leading to the solid-state structure with water-bridged double strands. Their complexation properties had been also studied by measurement of the stability constants for their complexation in a range of metal cations and investigation of their binding models via 1H NMR titration and ESI-MS experiments. It was found that the three ligands exhibited high and selective extractability toward Ag+, and their stoichiometry of ligand to Ag+ was 1:1, while the meta-aminopyridyl derivative showed the best extraction capacity and possessed the most efficient binding sites.
- Li, Xiong,Gong, Shu-Ling,Yang, Wei-Ping,Chen, Yuan-Yin,Meng, Xiang-Gao
-
p. 6230 - 6237
(2008/09/21)
-
- Experimental and computational studies of selective recognition of Hg 2+ by amide linked lower rim 1,3-dibenzimidazole derivative of calix[4]arene: Species characterization in solution and that in the isolated complex, including the delineation of the nanostructures
-
(Chemical Equation Presented) Amide linked lower rim 1,3-dibenzimidazole derivative of calix[4]arene, L has been shown to be sensitive and selective to Hg2+ in aqueous acetonitrile solution based on fluorescence spectroscopy, and the stoichiometry of the complexed species has been found to be 1:1. The selectivity of L toward Hg2+ has been shown among 11 M2+ ions, viz., Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg 2+, Pb2+, Ca2+, and Mg2+ studied, including those of the mercury group and none of these ions impede the recognition of Hg2+ by L. Role of the solvent on the recognition of Hg2+ has been demonstrated. The role of calix[4]arene platform and the benzimidazole moieties in the recognition of Hg2+ by L has been delineated upon performing such studies with five different molecules of relevance as reference molecular systems. The binding cores formed by the receptor L and the reference compounds have been established based on the single crystal XRD structures, and the preferential metal ion binding cores have been discussed. The binding of Hg2+ with L has been further established based on 1H and 13C NMR, ESI MS, absorption, and fluorescence lifetime measurements. Some of these techniques have been used to establish the stoichiometry of the species formed. The complex species formed between L and Hg2+ have been isolated and characterized and found to be 1:1 species even in the isolated complex. Whereas transmission electron microscopy (TEM), atomic force microscopy (AFM), and scanning electron microscopy (SEM) provided the nanostructural behavior of L, the TEM and SEM demonstrated that the mercury complex has different characteristics when compared to L. The TEM, SEM, and powder XRD studies revealed that whereas L is crystalline, that of the mercury complex is not, perhaps a reason for not being able to obtain single crystals of the complex. Binding characteristics of Hg2+ toward L have been established based on the DFT computational calculations.
- Joseph, Roymon,Ramanujam, Balaji,Acharya, Amitabha,Khutia, Anupam,Rao, Chebrolu P.
-
p. 5745 - 5758
(2008/12/22)
-
- (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)
-
- 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)
-
- Process for the preparation of alkyl aryl ethers containing carboxyl groups
-
Process for the preparation of alkyl aryl ethers containing carboxyl groups which are suitable for the preparation of colour film couplers, or derivatives thereof, by reaction of aromatic alcohols with alkyl halides containing carboxyl groups or derivatives thereof and basic alkali metal or alkaline earth metal compounds, characterized in that the reaction is carried out in the melt of the aromatic alcohol.
- -
-
-
- Cooperation of β-Cyclodextrin with Macrocyclic Metal Centers in the Action of Artificial Metalloesterases Built on Poly(ethylenimine)
-
β-Cyclodextrin (CD) was attached to poly(ethylenimine) (PEI), and then macrocyclic metal centers were constructed on the polymer by condensation with glyoxal or butanedione in the presence of metal (ZnII, NiII, or CoII) te
- Zoh, Kyung Duk,Lee, Sang Ho,Suh, Junghun
-
p. 242 - 252
(2007/10/02)
-
- Substituted heteroaralkyl, heteroaralkenyl or halomethyl fungicides
-
Compounds of the formula: STR1 wherein R is phenyl or phenyl substituted with 1 to 4 of the same or different substituents selected from fluoro, chloro, bromo, iodo, lower alkyl and trihalomethyl; R1 is lower alkyl; Y is lower alkenyl substituted with a 5- or 6-member heterocyclic ring containing 1 to 3 nitrogen atoms and the remainder of the ring atoms carbon atoms, or --CH2 W wherein W is fluoro, chloro, bromo, iodo, or a 5- to 6-member heterocyclic ring containing 1 to 3 nitrogen atoms and the remainder of the ring atoms carbon atoms; and X and Z are independently sulfur or oxygen; are effective fungicides.
- -
-
-
- Fungicidal (trihalophenoxy or trihalophenthio) alkylaminoalkyl pyridines and pyrroles
-
Compounds of the Formula: STR1 wherein X is sulfur or oxygen; R is phenyl or phenyl substituted with 1 to 3 substituents independently selected from fluoro, chloro, bromo, iodo, lower alkyl or trihalomethyl; R1 is lower alkyl or lower alkoxyalkyl; and R2 is 5- or 6-member heterocyclic ring having 1 to 3 ring nitrogens and the remainder of the ring atoms carbon atoms, optionally substituted with 1 to 2 independent lower alkyl groups, provided that a nitrogen of the 5- or 6-member heterocyclic ring is not bonded to the adjacent --CH2 -- group; or the group --CH2 --R3 wherein R3 is a 5- or 6-member heterocyclic ring having 1 to 3 ring nitrogens and the remainder of the ring atoms carbon atoms, are fungicidal.
- -
-
-
- N-Substituted phenoxyacetamide fungicides
-
The N-substituted phenoxyacetamides of this invention are effective fungicides. In particular, these compounds are particularly effective against Tomato Late Blight.
- -
-
-
- 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)
-
- T-Butyl-phenoxy-alkylene esters of benzoic and nicotinic acids, compositions containing same and their antihistaminic method of use
-
p-Alkyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: STR1 in which: R1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butyl; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane; R2 is lower alkyl having from one to three carbon atoms or hydrogen; R3 is hydroxyl or an ester group selected from the group consisting of COOR4 and OOCR4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR5 OOC and OOCR5 COO derived from unsubstituted and hydroxy-substituted dicarboxylic acids, the acids being selected from the group consisting of aliphatic acids, including carbamic acid, having from one to about twelve carbon atoms; cycloaliphatic acids having from three to about twelve carbon atoms; carbocyclic aromatic acids having from six to about twenty carbon atoms; and nitrogen heterocyclic aromatic acids having from five to about twelve carbon atoms, R4 being monovalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, and R5 being divalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, the acids being esterified with aliphatic alcohols having from one to six carbon atoms; and carbonic acid monoalkyl esters, the alkyl having from one to three carbon atoms; and n1, n2 and n3 represent the number of CH2, C(R2)2 and CH2 groups, respectively, and are numbers within the range from 0 to 10; and at least one of n1, n2 and n3 is other than zero. These compounds inhibit abnormal tissue reactivity due to specific allergic hypersensitivity or due to specific irritants by inhibiting the release of chemical mediators that are responsible for the symptoms of allergic diseases, including allergic rhinitis, asthma, hypersensitivity of the skin and of the gastrointestinal canal, and the many symptoms of irritation and inflammation produced by irritants and inflammation-causing substances.
- -
-
-
