176220-76-1

Basic information

• Product Name: (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
• Synonyms: (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
• CAS NO: 176220-76-1
• Molecular Weight: 439.532
• Mol File: 176220-76-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester(176220-76-1)
• EPA Substance Registry System: (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester(176220-76-1)

Safety Data

• Hazardous Substances Data: 176220-76-1(Hazardous Substances Data)

Upstream product

• 908093-98-1 diazodiphenylmethane 
• 75527-84-3 diphenylmethyl 6,6-dibromopenicillanate 
• 1266239-54-6 C₂₄H₂₄BrNO₅S 
• 305796-41-2 (2S,5R,6R)-6-bromo-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 76646-91-8 6,6-dibromopenicillanic acid-1,1-dioxide 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 81324-43-8 (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 

Downstream Products

• 305796-42-3 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-oxo-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 1266239-57-9 C₂₃H₂₅NO₆S 
• 1266239-70-6 C₂₃H₂₃NO₇S 
• 1266239-71-7 C₂₉H₃₈N₂O₇SSi 
• 305796-55-8 [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-[6-(4-methylphenylsulfonyl)-isoxazol-3-ylmethyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl 
• 305796-60-5 [2S,5R,6R]-3-(2-benzhydroxycarbonyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]hept-6-ylmethyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester 
• 305796-58-1 [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-benzoyl-isoxazol-3-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl 

Relevant articles and documents

Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy

In order to evaluate the importance of a hydrogen-bond donating substituent in the design of β-lactamase inhibitors, a series of C6-substituted penicillin sulfones, lacking a C2′ substituent, and having an sp 3 hybridized C6, was prepared and evaluated against a representative classes A and C β-lactamases. It was found that a C6 hydrogen-bond donor is necessary for good inhibitory activity, but that this feature alone is not sufficient in this series of C6β-substituted penicillin sulfones. Other factors which may impact the potency of the inhibitor include the steric bulk of the C6 substituent (e.g., methicillin sulfone) which may hinder recognition in the class A β-lactamases, and also high similarity to the natural substrates (e.g., penicillin G sulfone) which may render the prospective inhibitor a good substrate of both classes of enzyme. The best inhibitors had non-directional hydrogen-bonding substituents, such as hydroxymethyl, which may allow sufficient conformational flexibility of the acyl-enzyme for abstraction of the C6 proton by E166 (class A), thus promoting isomerization to the β-aminoacrylate as a stabilized acyl-enzyme.