187235-37-6 | (6S)-2-nitro-6-{[4-(trifluoromethoxy)phenyl]methoxy}-5H,6H,7H-imidazo[2,1-b][1,3]oxazine

Packsize	Purity	Availability	Price	Discounted Price
1mg	98%	in stock	$15.00	$11.00
5mg	98%	in stock	$38.00	$27.00
100mg	98%	in stock	$149.00	$104.00
250mg	98%	in stock	$287.00	$201.00

Description

• Catalog Number: AD32747
• Chemical Name: (6S)-2-nitro-6-{[4-(trifluoromethoxy)phenyl]methoxy}-5H,6H,7H-imidazo[2,1-b][1,3]oxazine
• CAS Number: 187235-37-6
• Molecular Formula: C14H12F3N3O5
• Molecular Weight: 359.2574
• MDL Number: MFCD06809939
• SMILES: [O-][N+](=O)c1cn2c(n1)OC[C@H](C2)OCc1ccc(cc1)OC(F)(F)F

Computed Properties

• Complexity: 468
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 25
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• XLogP3: 2.8

Literature

• Pentacyclic nitrofurans with in vivo efficacy and activity against nonreplicating Mycobacterium tuberculosis.

  PloS one 20140101

• Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis.

  Journal of natural products 20131025

• Preliminary structure-activity relationships and biological evaluation of novel antitubercular indolecarboxamide derivatives against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains.

  Journal of medicinal chemistry 20130523

• 14-day bactericidal activity of PA-824, bedaquiline, pyrazinamide, and moxifloxacin combinations: a randomised trial.

  Lancet (London, England) 20120915

• New drug combination for TB is tested in unique trial.

  BMJ (Clinical research ed.) 20120725

• Tuberculosis: the drug development pipeline at a glance.

  European journal of medicinal chemistry 20120501

• Structure-based design of novel benzoxazinorifamycins with potent binding affinity to wild-type and rifampin-resistant mutant Mycobacterium tuberculosis RNA polymerases.

  Journal of medicinal chemistry 20120426

• Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds.

  Bioorganic & medicinal chemistry 20120401

• Trial tests new combination of drugs to treat tuberculosis.

  BMJ (Clinical research ed.) 20120320

• Identification, design and biological evaluation of heterocyclic quinolones targeting Plasmodium falciparum type II NADH:quinone oxidoreductase (PfNDH2).

  Journal of medicinal chemistry 20120308

• Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2.

  European journal of medicinal chemistry 20120301

• Mouse model of necrotic tuberculosis granulomas develops hypoxic lesions.

  The Journal of infectious diseases 20120215

• Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

  Journal of medicinal chemistry 20120112

• Structure of Ddn, the deazaflavin-dependent nitroreductase from Mycobacterium tuberculosis involved in bioreductive activation of PA-824.

  Structure (London, England : 1993) 20120111

• Substrate specificity of the deazaflavin-dependent nitroreductase from Mycobacterium tuberculosis responsible for the bioreductive activation of bicyclic nitroimidazoles.

  The FEBS journal 20120101

• Rapid evaluation in whole blood culture of regimens for XDR-TB containing PNU-100480 (sutezolid), TMC207, PA-824, SQ109, and pyrazinamide.

  PloS one 20120101

• Integrative analysis of transcriptome and genome indicates two potential genomic islands are associated with pathogenesis of Mycobacterium tuberculosis.

  Gene 20111201

• Synthesis and structure-activity relationships of novel substituted 8-amino, 8-thio, and 1,8-pyrazole congeners of antitubercular rifamycin S and rifampin.

  Bioorganic & medicinal chemistry letters 20111015

• Synthesis and structure-activity relationships of varied ether linker analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine (PA-824).

  Journal of medicinal chemistry 20111013

• Pharmacophore modeling and density functional theory analysis for a series of nitroimidazole compounds with antitubercular activity.

  Chemical biology & drug design 20110901

• Structure-activity relationships of antitubercular nitroimidazoles. 3. Exploration of the linker and lipophilic tail of ((s)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-amino PA-824).

  Journal of medicinal chemistry 20110825

• The TB Alliance: overcoming challenges to chart the future course of TB drug development.

  Future medicinal chemistry 20110801

• Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity.

  European journal of medicinal chemistry 20110601

• Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles.

  Bioorganic & medicinal chemistry 20110601

• Novel thiolactone-isatin hybrids as potential antimalarial and antitubercular agents.

  Bioorganic & medicinal chemistry letters 20110401

• Synthesis and antitubercular activity of monocyclic nitroimidazoles: insights from econazole.

  Bioorganic & medicinal chemistry letters 20110301

• The effect of 5-substitution on the electrochemical behavior and antitubercular activity of PA-824.

  Bioorganic & medicinal chemistry letters 20110115

• Comparative bioactivation of the novel anti-tuberculosis agent PA-824 in Mycobacteria and a subcellular fraction of human liver.

  British journal of pharmacology 20110101

• Half-century-old TB drugs get a facelift in new cocktails.

  Nature medicine 20101201

• A concise and convergent synthesis of PA-824.

  The Journal of organic chemistry 20101105

• Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring.

  Bioorganic & medicinal chemistry 20101015

• The nitroimidazooxazines (PA-824 and analogs): structure-activity relationship and mechanistic studies.

  Future medicinal chemistry 20100801

• Synthesis, antimalarial and antitubercular activity of acetylenic chalcones.

  Bioorganic & medicinal chemistry letters 20100201

• Synthesis and structure-activity relationships of antitubercular 2-nitroimidazooxazines bearing heterocyclic side chains.

  Journal of medicinal chemistry 20100128

• Rational design of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters as growth inhibitors of Mycobacterium tuberculosis. a potent and selective series for further drug development.

  Journal of medicinal chemistry 20100128

• Release of nitrite from the antitubercular nitroimidazole drug PA-824 and analogues upon one-electron reduction in protic, non-aqueous solvent.

  Organic & biomolecular chemistry 20100121

• Synthesis and structure-activity studies of biphenyl analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

  Journal of medicinal chemistry 20100114

• Discovery and development of the covalent hydrates of trifluoromethylated pyrazoles as riboflavin synthase inhibitors with antibiotic activity against Mycobacterium tuberculosis.

  The Journal of organic chemistry 20090807

• Structure-activity relationships of antitubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles.

  Journal of medicinal chemistry 20090312

• Structure-activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships.

  Journal of medicinal chemistry 20090312

• Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

  Journal of medicinal chemistry 20090212

• Microbiology. An antibiotic mimics immunity.

  Science (New York, N.Y.) 20081128

• PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release.

  Science (New York, N.Y.) 20081128

• A microbiological assessment of novel nitrofuranylamides as anti-tuberculosis agents.

  The Journal of antimicrobial chemotherapy 20081101

• Crystal structures of F420-dependent glucose-6-phosphate dehydrogenase FGD1 involved in the activation of the anti-tuberculosis drug candidate PA-824 reveal the basis of coenzyme and substrate binding.

  The Journal of biological chemistry 20080620

• Intermediates in the reduction of the antituberculosis drug PA-824, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine, in aqueous solution.

  Organic & biomolecular chemistry 20080607

• Synthesis and antitubercular activity of 7-(R)- and 7-(S)-methyl-2-nitro-6-(S)-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazines, analogues of PA-824.

  Bioorganic & medicinal chemistry letters 20080401

• [Some new antitubercular agents].

  Revue medicale suisse 20080319

• PA-824.

  Tuberculosis (Edinburgh, Scotland) 20080301

• Comparison of the sterilising activities of the nitroimidazopyran PA-824 and moxifloxacin against persisting Mycobacterium tuberculosis.

  The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 20080101

• New anti-tuberculosis drugs with novel mechanisms of action.

  Current medicinal chemistry 20080101

• Advances in the treatment of tuberculosis.

  Clinical pharmacology and therapeutics 20071101

• NLCQ-1 and NLCQ-2, two new agents with activity against dormant Mycobacterium tuberculosis.

  International journal of antimicrobial agents 20070601

• OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice.

  PLoS medicine 20061101

• Combination chemotherapy with the nitroimidazopyran PA-824 and first-line drugs in a murine model of tuberculosis.

  Antimicrobial agents and chemotherapy 20060801

• NIAID researchers make key discovery in development of TB drug candidate.

  Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20060301

• Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis.

  Proceedings of the National Academy of Sciences of the United States of America 20060110

• New tuberculosis drug enters human trials.

  The Lancet. Infectious diseases 20050801

• New small-molecule synthetic antimycobacterials.

  Antimicrobial agents and chemotherapy 20050601

• Bactericidal activity of the nitroimidazopyran PA-824 in a murine model of tuberculosis.

  Antimicrobial agents and chemotherapy 20050601

• Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models.

  Antimicrobial agents and chemotherapy 20050601

• [Anti-tuberculosis drugs].

  Nihon rinsho. Japanese journal of clinical medicine 20030201

• A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis.

  Nature 20000622