81324-43-8

Basic information

• Product Name: BENZHYDRYL 6,6-DIBROMOPENICILLINATE SULFONE
• Synonyms: BENZHYDRYL 6,6-DIBROMOPENICILLINATE SULFONE;Benzhydryl dibromopenicillinate sulfone
• CAS NO: 81324-43-8
• Molecular Formula: C₂₁H₁₉Br₂NO₅S
• Molecular Weight: 557.25
• Mol File: 81324-43-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 654.3°C at 760 mmHg
• Flash Point: 349.5°C
• Appearance: /
• Density: 1.77g/cm³
• Vapor Pressure: 5.32E-17mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: BENZHYDRYL 6,6-DIBROMOPENICILLINATE SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZHYDRYL 6,6-DIBROMOPENICILLINATE SULFONE(81324-43-8)
• EPA Substance Registry System: BENZHYDRYL 6,6-DIBROMOPENICILLINATE SULFONE(81324-43-8)

Safety Data

• Hazardous Substances Data: 81324-43-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H19Br2NO5S/c1-20(2)16(24-18(26)21(22,23)19(24)30(20,27)28)17(25)29-15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15-16,19H,1-2H3/t16-,19?/m0/s1

Upstream product

• 908093-98-1 diazodiphenylmethane 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 76646-91-8 6,6-dibromopenicillanic acid-1,1-dioxide 
• 75527-84-3 diphenylmethyl 6,6-dibromopenicillanate 

Downstream Products

• 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 
• 345203-88-5 (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 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 
• 176220-76-1 (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 
• 305796-43-4 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 305796-45-6 (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 305796-44-5 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-chloro-2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 305796-51-4 [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-(5-methoxycarbonyl-isoxazol-3-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl 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.

6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases I

Five 6-(1-hydroxyalkyl)penam sulfone derivatives and two 6- (hydroxymethyl)penams were synthesized for β-lactamase inhibitor screens. The substituent effects and stereochemical requirements of 6α-and 6β-(1- hydroxyalkyl) groups for the biological activity of penam sulfone derivatives were investigated. Of these substituents, only the 6β-hydroxymethyl group of 15 improved the activity of sulbactam against both TEM-1 and AmpC β- lactamases. The sulfone moiety is required for the enhancement of the β- lactamase inhibitory activity. 6β-Hydroxymethylsulbactam (15) was able to restore the activity of piperacillin in vitro and in vivo against various β- lactamase producing microorganisms.