623931-24-8

Basic information

• Product Name: 4-nitrobenzyl 6-[(acetyloxy)(5-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: 4-nitrobenzyl 6-[(acetyloxy)(5-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate
• CAS NO: 623931-24-8
• Molecular Weight: 643.495
• Mol File: 623931-24-8.mol

Chemical Properties

• CAS DataBase Reference: 4-nitrobenzyl 6-[(acetyloxy)(5-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrobenzyl 6-[(acetyloxy)(5-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate(623931-24-8)
• EPA Substance Registry System: 4-nitrobenzyl 6-[(acetyloxy)(5-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate(623931-24-8)

Safety Data

• Hazardous Substances Data: 623931-24-8(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 623564-16-9 (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester 
• 623931-23-7 2-formyl-5-methylimidazo[2,1-b]benxothiazole 
• 1477-42-5 4-methyl-1,3-benzothiazol-2-amine 
• 149210-23-1 ethyl 12-methyl-7-thia-2,5-diazatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,3,5,9,11-pentaene-4-carboxylate 
• 349480-84-8 5-methylimidazo[2,1-b]benzothiazole-2-methanol 

Relevant articles and documents

Tricyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors

This invention relates to certain tricyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present inventio

Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum β-lactamase inhibitors: Crystallographic structures show unexpected binding of 1,4-thiazepine intermediates

The design and synthesis of a series of seven tricyclic 6-methylidene penems as novel class A and C serine β-lactamase inhibitors is described. These compounds proved to be very potent inhibitors of the TEM-1 and AmpC β-lactamases and less so against the class B metallo-β-lactamase CcrA. In combination with piperacillin, their in vitro activities enhanced susceptibility of all class C resistant strains from various bacteria. Crystallographic structures of a serine-bound reaction intermediate of 17 with the class A SHV-1 and class C GC1 enzymes have been established to resolutions of 2.0 and 1.4 A?, respectively, and refined to R-factors equal 0.163 and 0.145. In both β-lactamases, a seven-membered 1,4-thiazepine ring has formed. The stereogenic C7 atom in the ring has the R configuration in the SHV-1 intermediate and has both R and S configurations in the GC1 intermediate. Hydrophobic stacking interactions between the tricyclic C7 substituent and a tyrosine side chain, rather than electrostatic or hydrogen bonding by the C3 carboxylic acid group, dominate in both complexes. The formation of the 1,4- thiazepine ring structures is proposed based on a 7-endo-trig cyclization.