162252-97-3

Basic information

• Product Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-(2-pyridinylmethylene)-, diphenylmethyl ester, (6R,7Z)-
• CAS NO: 162252-97-3
• Molecular Formula: C29H24N2O5S
• Molecular Weight: 512.586
• Mol File: 162252-97-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-(2-pyridinylmethylene)-, diphenylmethyl ester, (6R,7Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-(2-pyridinylmethylene)-, diphenylmethyl ester, (6R,7Z)-(162252-97-3)
• EPA Substance Registry System: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-(2-pyridinylmethylene)-, diphenylmethyl ester, (6R,7Z)-(162252-97-3)

Safety Data

• Hazardous Substances Data: 162252-97-3(Hazardous Substances Data)

Upstream product

• 54600-89-4 benzhydryl 7β-aminocephalosporanate 
• 908093-98-1 diazodiphenylmethane 
• 4377-33-7 2-chloromethylpyridine 
• 59128-53-9 benzhydryl 7-oxocephalosporanate 
• 38700-15-1 triphenyl-(2-pyridylmethyl)phosphonium chloride 
• 957-68-6 7-Aminocephalosporanic acid 

Downstream Products

• 287489-61-6 (R)-3-((E)-2-tert-Butoxycarbonyl-vinyl)-4-methylene-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-43-4 (R)-3-((E)-2-tert-Butoxycarbonyl-vinyl)-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-60-5 (R)-3-((E)-2-Methoxycarbonyl-vinyl)-4-methylene-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-40-1 (R)-3-((E)-2-Carbamoyl-vinyl)-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287410-58-6 (R)-3-Acetoxymethyl-4-methylene-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-39-8 (R)-3-((E)-2-Methoxycarbonyl-vinyl)-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-42-3 (R)-3-((E)-Buta-1,3-dienyl)-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-35-4 (2R,6R)-3-((Z)-2-Chloro-2-methoxycarbonyl-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 287489-38-7 (R)-3-((E)-2-Cyano-vinyl)-5,5,8-trioxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 287489-37-6 (2R,6R)-3-((E)-2-tert-Butoxycarbonyl-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 287489-34-3 (2R,6R)-3-((E)-2-Carbamoyl-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 287489-33-2 (2R,6R)-3-((E)-2-Methoxycarbonyl-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 287488-98-6 (2R,6R)-3-((E)-2-Nitro-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 287489-31-0 (2R,6R)-3-((E)-2-Cyano-vinyl)-8-oxo-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

The synthesis and evaluation of 2-substituted-7-(alkylidene)cephalosporin sulfones as β-lactamase inhibitors

A series of 2-substituted-7-(alkylidene)cephalosporin sulfones were prepared and evaluated as β-lactamase inhibitors. Compound 11c showed excellent activity as an inhibitor of the class C β-lactamase derived from Enterobacter cloacae, strain P99. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis and biological activity of 7-alkylidenecephems

Several 7-alkylidenecephalosporins were synthesized and biologically evaluated as β-lactamase inhibitors. The three β-lactamase enzymes used in this study included two type C β-lactamases, derived from Enterobacter cloacae P99 and E. cloacae SC12368, and one type A β-lactamase, derived from Escherichia coli WC3310. Of the cephalosporins prepared, compound 7e, the sodium salt of 7-[(Z)-(2'-pyridyl)methylene]cephalosporanic acid sulfone, was found to have excellent inhibitory properties against both type C enzymes. Also, compound 7f, the sodium salt of 7-[(Z)-(tert- butoxycarbonyl)methylene]cephalosporanic acid sulfone showed high activity as an inhibitor of the type A enzyme. The inhibition kinetics of 7e were further explored. The IC50 value of 7e indicated that this compound was approximately 20-fold more active than tazobactam against the enzyme derived from E. cloacae P99 and 167-fold more active than tazobactam against the enzyme derived from E. cloacae SC12368. A plot of enzymatic activity vs incubation time with stoichiometric amounts of inhibitor reveals a rapid deactivation of the enzyme followed by an extremely slow reactivation. 7e exhibited a second-order rate constant of k3' = 5.3 x 106 L/mol · min, and a partition ratio of approximately 20:1 inhibitor:enzyme was determined for this inhibitor. After separation of excess inhibitor with Sephadex filtration, a rate constant of enzyme reactivation was measured at k(reactiv) = 1.0 x 10-3 s-1. Following 24 h of incubation of enzyme with a large excess of inhibitor and sephadex filtration to remove excess inhibitor, the enzyme was able to recover only 43% of its original activity, indicating an irreversible component to the inhibition. Potential mechanisms of inhibition for both 7e and 7f are suggested.