623906-12-7

Basic information

• Product Name: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)[1-methyl-2-(2-thiazolyl)-1H-imidazol-4-yl]methyl]-6-bromo- 7-oxo-, (4-nitrophenyl)methyl ester, (5R)-
• CAS NO: 623906-12-7
• Molecular Formula: C23H18BrN5O7S2
• Molecular Weight: 620.461
• Mol File: 623906-12-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)[1-methyl-2-(2-thiazolyl)-1H-imidazol-4-yl]methyl]-6-bromo- 7-oxo-, (4-nitrophenyl)methyl ester, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)[1-methyl-2-(2-thiazolyl)-1H-imidazol-4-yl]methyl]-6-bromo- 7-oxo-, (4-nitrophenyl)methyl ester, (5R)-(623906-12-7)
• EPA Substance Registry System: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)[1-methyl-2-(2-thiazolyl)-1H-imidazol-4-yl]methyl]-6-bromo- 7-oxo-, (4-nitrophenyl)methyl ester, (5R)-(623906-12-7)

Safety Data

• Hazardous Substances Data: 623906-12-7(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 
• 623906-10-5 1-methyl-2-thiazol-2-yl-1H-imidazole-4-carbaldehyde 
• 279251-07-9 2-thiazol-2-yl-1H-imidazole-4-carbaldehyde 

Relevant articles and documents

Novel imidazole substituted 6-methylidene-penems as broad-spectrum β-lactamase inhibitors

A series of novel imidazole substituted 6-methylidene-penems has been synthesized (R = heterocycle) and was shown to be potent, broad-spectrum β-lactamase inhibitors against class-A and class-C enzymes. The present paper deals with the design, synthesis, and structure-activity relationships (SAR) of compounds 11-15. β-Lactamases are serine and metallo-dependent enzymes produced by the bacteria in defense against β-lactam antibiotics. Production of class-A, class-B, and class-C enzymes by the bacteria make the use of β-lactam antibiotics ineffective in certain cases. To overcome resistance to β-lactam antibiotics, several β-lactamase inhibitors such as clavulanic acid, sulbactam, and tazobactam are widely used in the clinic in combination with β-lactam antibiotics. However, single point mutations within these enzymes have allowed bacteria to overcome the inhibitory effect of the commercially approved β-lactamase inhibitors. Although the commercially available β-lactamase inhibitor/β-lactam antibiotic combinations are effective against class-A producing bacteria and many extended spectrum β-lactamase (ESBL's) producing bacteria they are less effective against class-C enzymes expressing bacteria. To circumvent this problem, based on modeling studies several novel imidazole substituted 6-methylidene-penem derivatives were synthesized and tested against various β-lactamase producing isolates. The present paper deals with the synthesis and structure-activity relationships (SAR) of these compounds.

PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES

The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.