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	99%	in stock	$20.00	$14.00
5mg	99%	in stock	$43.00	$30.00
100mg	99%	in stock	$163.00	$114.00
250mg	99%	in stock	$287.00	$201.00
1g	99%	in stock	$712.00	$498.00
5g	99%	in stock	$1,779.00	$1,245.00

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

Upstream Synthesis Route

(6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine plays a crucial role in chemical synthesis as a versatile building block. This compound exhibits unique properties that make it highly valuable for creating complex molecules in the laboratory setting. Chemists utilize (6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine as a key reagent in the formation of various pharmaceuticals, agrochemicals, and advanced materials. Its specific structure enables precise manipulation during reactions, leading to the synthesis of important intermediates and final products essential for diverse industries.

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