1202941-75-0

Basic information

• Product Name: (6S)-2-nitro-6-({1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• Synonyms: (6S)-2-nitro-6-({1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• CAS NO: 1202941-75-0
• Molecular Weight: 425.324
• Mol File: 1202941-75-0.mol

Chemical Properties

• CAS DataBase Reference: (6S)-2-nitro-6-({1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-2-nitro-6-({1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(1202941-75-0)
• EPA Substance Registry System: (6S)-2-nitro-6-({1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(1202941-75-0)

Safety Data

• Hazardous Substances Data: 1202941-75-0(Hazardous Substances Data)

Upstream product

• 187235-08-1 (S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol 
• 1202942-24-2 4-(bromomethyl)-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole 
• 1202942-23-1 {1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methanol 
• 1202942-22-0 ethyl 1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylate 
• 400073-87-2 ethyl 5-amino-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylate 

Relevant articles and documents

NITROIMIDAZOOXAZINES AND THEIR USES IN ANTI-TUBERCULAR THERAPY

The present invention relates to novel nitroimidazooxazines, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.

NITROIMIDAZOOXAZINES AND THEIR USES IN ANTI-TUBERCULAR THERAPY

The present invention relates to novel nitroimidazooxazines, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.

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

Recently described biphenyl analogues of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility. 2009 American Chemical Society.