1263417-25-9

Basic information

• Product Name: 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole
• Synonyms: 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole
• CAS NO: 1263417-25-9
• Molecular Weight: 658.588
• Mol File: 1263417-25-9.mol

Chemical Properties

• CAS DataBase Reference: 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole(1263417-25-9)
• EPA Substance Registry System: 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole(1263417-25-9)

Safety Data

• Hazardous Substances Data: 1263417-25-9(Hazardous Substances Data)

Upstream product

• 1263417-23-7 (2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[(triisopropylsilyl)oxy]-1-propanol 
• 1263417-22-6 4-[(1S)-(2-benzyloxy-1-{triisopropylsilyloxymethyl}ethyl)oxy]-4'-trifluoromethoxy-1,1'-biphenyl 
• 1263417-21-5 (2R)-1-benzyloxy-3-triisopropylsilyloxy-2-propanol 
• 1263417-24-8 4-[(1R)-(2-iodo-1-{[triisopropylsilyloxy]methyl}ethyl)oxy]-4'-trifluoromethoxy-1,1'-biphenyl 
• 65902-59-2 2-bromo-4-nitro-1H-imidazole 

Downstream Products

• 1263417-07-7 (6S)-2-nitro-6-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 
• 1263417-26-0 C₁₉H₁₅BrF₃N₃O₅ 

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.

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

New analogues of antitubercular drug PA-824 were synthesized, featuring alternative side chain ether linkers of varying size and flexibility, seeking drug candidates with enhanced metabolic stability and high efficacy. Both α-methyl substitution and removal of the benzylic methylene were broadly tolerated in vitro, with a biaryl example of the latter class exhibiting an 8-fold better efficacy than the parent drug in a mouse model of acute Mycobacterium tuberculosis infection and negligible fragmentation to an alcohol metabolite in liver microsomes. Extended linkers (notably propenyloxy, propynyloxy, and pentynyloxy) provided greater potencies against replicating M. tb (monoaryl analogues), with propynyl ethers being most effective under anaerobic (nonreplicating) conditions (mono/biaryl analogues). For benzyloxybenzyl and biaryl derivatives, aerobic activity was maximal with the original (OCH2) linker. One propynyloxy-linked compound displayed an 89-fold higher efficacy than the parent drug in the acute model, and it was slightly superior to antitubercular drug OPC-67683 in a chronic infection model.

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.