187235-28-5

Basic information

• Product Name: (6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• CAS NO: 187235-28-5
• Molecular Formula: C₂₀H₁₉N₃O₅
• Molecular Weight: 381.382
• Mol File: 187235-28-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 587.1°C at 760 mmHg
• Flash Point: 308.8°C
• Density: 1.35g/cm³
• Vapor Pressure: 9.17E-14mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: (6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(187235-28-5)
• EPA Substance Registry System: (6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine(187235-28-5)

Safety Data

• Hazardous Substances Data: 187235-28-5(Hazardous Substances Data)

Usage

General Description

"(6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine" is a chemical compound with a complex structure. It contains a nitro group, a benzyloxyphenyl group, and an imidazo[2,1-b][1,3]oxazine ring. (6S)-6-[(4-benzyloxyphenyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine is a potential pharmaceutical agent with the ability to interact with biological systems in a specific way. Its unique structure suggests that it may have various biological activities, and it could be of interest for further study in drug development or medicinal chemistry. Further research is needed to fully understand the potential uses and properties of this compound.

Upstream product

• 187235-08-1 (S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol 
• 836-42-0 4-benzyloxybenzyl chloride 

Relevant articles and documents

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.