- Two crystalline polymorphic forms of α-(N-benzoxazolin-2-one)acetic acid
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Two crystalline polymorphic forms of α-(N-benzoxazolin-2-one)acetic acid (BAA) are prepared by changing the temperature of its crystallization from solution in ethanol. Crystallographic data of the α-form are determined: a = 12.7769(17) ?, b = 8.2574(9) ?, c = 16.7390(19) ?, β = 105.087(13)°, space group C2/c, V = 1705.2(4) ?3, and Z = 8, while those of β form are a = 5.2854(4) ?, b = 5.9880(4) ?, c = 13.4509(5) ?, β = 94.666(4)°, space group P21, V = 424.30(4) ?3, and Z = 2. It is found that BAA molecules of the α form combine into infinite one-dimensional chains arranged along axis b by means of O?H···O and C?H···O hydrogen bonds, and these chains are crosslinked via C?H···O hydrogen bonds to form a threedimensional structure. The β form has another system of hydrogen bonds, one of which is bifurcated (O4···O2, O4···O3), and the π–π-interactions between the benzoxazolinone fragments of BAA molecules combined into a chain also arranged along axis b are observed. Calorimetric analysis shows that the polymorphic transition from the α form to the β form occurs at 129°C.
- Ashurov,Izotova, L. Yu.,Ibragimov,Mukhamedov
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- Complexes of acetic acid α-(N-Benzoxazolin-2-one) with Zn(II), Cu(II), and Co(II): Syntheses and crystal structures
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The results of syntheses and X-ray diffraction analyses of mononuclear complexes [ML2 (H2O)4] (M = Co2+(I), Cu2+(II), and Zn2+(III)) containing water molecules and anions of acetic acid α-(N-benzox -azolin-2-one) (L = C9H 6O4) are presented. The crystals of complexes I-III are isostructural (space group P22/n, Z = 2) and are built of discrete neutral complex molecules. The crystallographic data are as follows: for complex I, a = 6.1470(5), b = 5.3310(3), c = 30.5894(17) A, β = 95.056(6)°, V = 998.50(11) A3; for com -plex II, a = 5.9661(6) A, b = 5.1414(4) A, c = 32.672(2) A, β = 92.395(6)°, V = 1001.33(14) A3; and for com -plex III, a = 6.1404(3) A, b = 5.3476(2) A, c = 30.5865(12) A, β = 94.708(4)°, V = 1000.96(7) A3. The metal atoms (M) of the complexing agents are localized in the crystallographic symmetry centers and have a distorted octahedral environment due to two oxygen atoms of the carboxy groups of two monodentate ligands (L) and four water molecules. The M-O(1w)(H2O) and M-O(2w)(H2O) bond lengths for the indi -cated complexes are 2.088(3) and 2.118(3), 2.446(3) and 1.971(3), and 2.113(4) and 2.093(3) A for M = Co2+, Cu2+, and Zn2+, respectively. The crystal structures are formed due to packing of chains built of inter -molecular hydrogen bonds O-H·O.
- Ashurov,Ibragimov,Muv
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- Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA
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A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl)acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl)acetamide (30) was found to be the most promising compound with IC50 of 5.12 ± 0.44 μM against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 μM and was non-cytotoxic at 100 μM. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry.
- Pedgaonkar, Ganesh S.,Sridevi, Jonnalagadda Padma,Jeankumar, Variam Ullas,Saxena, Shalini,Devi, Parthiban Brindha,Renuka, Janupally,Yogeeswari, Perumal,Sriram, Dharmarajan
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- Synthesis and in silico studies of Novel Ru(II) complexes of Schiff base derivatives of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl)methyl]-2(3H)-benzoxazolone compounds as potent Glutathione S-transferase and Cholinesterases Inhibitor
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Novel Ru(II) complexes of Shiff base derivatives of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl)methyl]-2(3H)-benzoxazolone were synthesized. The ligands (1a-e) were confirmed by IR, 1H NMR, and 13C NMR spectra (only 1b and 1c). Structures of the synthesized Ru(II) complexes (2a-e) were illuminated by elemental analysis, IR, 1H NMR, 13C NMR, and mass spectra. As the biological studies, the inhibitory potency of the ligands and the novel synthesized complexes were evaluated against the glutathione S-transferase (GST), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes in vitro conditions. Ki values in the range of 26.87-47.63 μM for AChE, 23.51-42.81 μM for BChE, and 33.14-51.73 μM for GST, respectively. The free binding energy of most active inhibitors against AChE, BChE, and GST enzymes were detected as -10.183 kcal/mol, -9.111 kcal/mol, and -6.097 kcal/mol, respectively. All compounds docked were observed to bind in the active site of the enzymes with similar binding orientation and binding interactions with the surrounding amino acids.
- Adiguzel, Ragip,Türkan, Fikret,Yildiko, ümit,Aras, Abdülmelik,Evren, Enes,Onkol, Tijen
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- A Metallaphotoredox Method for the Expansion of Benzyl SAR on Electron-Deficient Amines
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A metallaphotoredox reaction is described that allows for the efficient exploration of benzyl structure-activity relationships on electron-deficient amines. Typically, accessing a variety of benzyl groups on these substrates can be difficult due to the limited availability of the prerequisite building blocks, namely benzyl halides. However, the use of aryl bromides in this metallaphotoredox reaction allows for greater diversity in the benzyl piece. The reaction scope is discussed herein, including conditions for product scaleup using flow.
- Shea, Meghan D.,Mansoor, Umar Faruk,Hopkins, Brett A.
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supporting information
p. 1052 - 1055
(2020/02/15)
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- Mild and versatile potassium fluoride/tetrabutylammonium fluoride protocol for ester hydrolysis
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A mild and versatile protocol of potassium fluoride/tetrabutylammonium fluoride (KF/TBAF) in aqueous tetrahydrofuran for ester hydrolysis has been developed. The method is applied on variety of aliphatic and aromatic ester moieties bearing acid or base sensitive functional groups. The conditions have been also applied on acetates to yield alcohols. The chirality of optically pure esters remained intact with the conditions of the reaction.
- Vijayalakshmi,Balakrishna,Mustafa, Shaik
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p. 309 - 311
(2018/01/11)
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- Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists
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A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit 1. The dihydroindolyl glycinamide 10a significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide 12c also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both compounds 10a and 12c represent potential tools for further investigation into the biology of the NPY5 receptor.
- Wu, Lingyun,Lu, Kai,Packiarajan, Mathivanan,Jubian, Vrej,Chandrasena, Gamini,Wolinsky, Toni C.,Walker, Mary W.
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scheme or table
p. 2167 - 2171
(2012/04/18)
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- Schiff bases of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl) methyl]-2(3H)-benzoxazolone derivatives: Synthesis and biological activity
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New Schiff base derivatives of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl) methyl]-2(3H)-benzoxazolone with aromatic aldehydes have been synthesized under microwave irradiation. Structures of the synthesized compounds were confirmed by IR, 1H-NMR and elemental analysis. Variable, but modest antimicrobial and antitubercular activity against the investigated strains of bacteria and fungi were observed. Among the derivatives obtained, 4-bromophenylmethylidene derivative 5j revealed significant antibacterial activity against P. aeruginosa.
- Urlu Cicekli, Solen,Onkol, Tijen,Ozgen, Selda,Sahin, M. Fethi
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p. 187 - 195
(2013/02/23)
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- Design, biologic evaluation, and SAR of novel pseudo-peptide incorporating benzheterocycles as HIV-1 protease inhibitors
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A series of novel HIV-1 protease inhibitors based on the (hydroxyethylamino)-sulfonamide isostere incorporating substituted phenyls and benzheterocycle derivatives bearing rich hydrogen bonding acceptors as P 2 ligands were synthesized. Prolonged chain linking the benzhereocycle to the carbonyl group resulted in partial loss of binding affinities. Introduction of a small alkyl substituent with appropriate size to the -CH2- of P1-P2 linkage as a side chain resulted in improved inhibitory potency, and in this study, isopropyl was the best side chain. Replacement of the isobutyl substituent at P 1′group with phenyl substituent decreased the inhibitory potency. One of the most potent inhibitor, compound 23 showing high affinity to HIV-1 protease with an IC50 value of 5 nm, also exhibited good anti-SIV activity (EC50 = 0.8 μm) with low toxicity (TC 50 > 100 μm). The flexible docking of inhibitor 23 to HIV-1 protease active site rationalized the interactions with protease.
- He, Meizi,Zhang, Hang,Yao, Xiaojian,Eckart, Michael,Zuo, Elizabeth,Yang, Ming
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scheme or table
p. 174 - 180
(2011/03/20)
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- MORPHOLINYL AND PYRROLIDINYL ANALOGS
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The present invention relates to morpholinyl, and pyrrolidinyl analogs, pharmaceutical compositions containing them, and their use as antagonists of urotensin II.
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Page/Page column 20
(2008/06/13)
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- Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists
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A rapid analogue approach to identification of spirohydantoin-based CGRP antagonists provided novel, low molecular weight leads. Modification of these leads afforded a series of nanomolar benzimidazolinone-based CGRP receptor antagonists. The oral bioavai
- Bell, Ian M.,Bednar, Rodney A.,Fay, John F.,Gallicchio, Steven N.,Hochman, Jerome H.,McMasters, Daniel R.,Miller-Stein, Cynthia,Moore, Eric L.,Mosser, Scott D.,Pudvah, Nicole T.,Quigley, Amy G.,Salvatore, Christopher A.,Stump, Craig A.,Theberge, Cory R.,Wong, Bradley K.,Zartman, C. Blair,Zhang, Xu-Fang,Kane, Stefanie A.,Graham, Samuel L.,Vacca, Joseph P.,Williams, Theresa M.
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p. 6165 - 6169
(2007/10/03)
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- Ramoplanin derivatives possessing antibacterial activity
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Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
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Page/Page column 64
(2010/11/23)
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- Compounds that modulate PPAR activity and methods of preparation
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This invention relates to compounds that alter PPAR activity. The invention also relates to pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing dyslipidemia, hypercholesterolemia, obesity, hyperglycemia, atherosclerosis, hypertriglyceridemia and hyperinsulinemia in a mammal. The present invention also relates to methods for making the disclosed compounds.
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