75527-84-3

Basic information

• Product Name: BENZYL 6,6-DIBROMOPENICILLANATE
• Synonyms: BENZYL 6,6-DIBROMOPENICILLANATE;(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester;(5R)-3,3-Dimethyl-6,6-dibromo-7-oxo-1-aza-4-thiabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester;6,6-Dibromopenicillanic acid benzhydryl ester;6,6-Dibromo-Benzhydryl-Penicillanate
• CAS NO: 75527-84-3
• Molecular Formula: C₂₁H₁₉Br₂NO₃S
• Molecular Weight: 449.16
• Mol File: 75527-84-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 574.4°C at 760 mmHg
• Flash Point: 301.2°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 3.38E-13mmHg at 25°C
• Refractive Index: 1.691
• Solubility: Dichloromethane
• CAS DataBase Reference: BENZYL 6,6-DIBROMOPENICILLANATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 6,6-DIBROMOPENICILLANATE(75527-84-3)
• EPA Substance Registry System: BENZYL 6,6-DIBROMOPENICILLANATE(75527-84-3)

Safety Data

• Hazardous Substances Data: 75527-84-3(Hazardous Substances Data)

Usage

Description

BENZYL 6,6-DIBROMOPENICILLANATE is a chemical compound that serves as an impurity in the synthesis of Tazobactam-d4, which is the labeled analog of Tazobactam (T010095). Tazobactam is a β-Lactamase inhibitor, commonly used in combination with β-lactam antibiotics to enhance their effectiveness.

Uses

Used in Pharmaceutical Industry:
BENZYL 6,6-DIBROMOPENICILLANATE is used as an intermediate in the synthesis process for Tazobactam-d4, a labeled analog of Tazobactam. BENZYL 6,6-DIBROMOPENICILLANATE plays a crucial role in the development and production of Tazobactam, a β-Lactamase inhibitor that is used in combination with β-lactam antibiotics to improve their efficacy against bacterial infections. By enhancing the effect of these antibiotics, Tazobactam helps in the treatment of various bacterial diseases and contributes to the overall advancement of pharmaceutical research and development.

InChI:InChI=1/C21H19Br2NO3S/c1-20(2)16(24-18(26)21(22,23)19(24)28-20)17(25)27-15(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 
• 551-16-6 6-aminopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 

Downstream Products

• 73968-83-9 benzhydryl 6,6-dihydropenicillate 
• 108834-87-3 benzhydryl 6β-(2'-acetoxyethyl)penicillanate 
• 108834-84-0 benzhydryl 6α-(2'-acetoxyethyl)penicillanate 
• 108834-95-3 benzhydryl 6,6-diallylpenicillanate 
• 77233-35-3 benzhydryl 6β-allylpenicillanate 
• 75527-85-4 benzhydryl 6β-bromopenicillanate 
• 100298-37-1 (4S,5R)-6,6-Dibromo-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 100298-37-1 benzhydryl 6,6-dibromopenicillanate 1α-oxide 
• 123285-25-6 diphenylmethyl (4R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4-oxide 
• 98153-30-1 (2S,5R)-6-Bromo-6-(hydroxy-phenyl-methyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 129543-95-9 2-(2-Acetylsulfanyl-3,3-dibromo-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzhydryl ester 
• 108834-85-1 benzhydryl 6β-(2'-cyanoethyl)penicillanate 
• 108834-82-8 benzhydryl 6α-(2'-cyanoethyl)penicillanate 
• 108834-86-2 benzhydryl 6β(2'-carbomethoxyethyl)penicillanate 

Relevant articles and documents

C type beta-lactamase inhibitor, and preparation method and applications thereof

The invention provides a C type beta-lactamase inhibitor. The C type beta-lactamase inhibitor is 6 alpha-(1R-hydroxy-3(2-thiophene-yl)propyl) penicillic acid, and the structure of the C type beta-lactamase inhibitor is represented by formula 1 in the invention.

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.

Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases

The synthesis and β-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl) penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-β-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-β-lactamases and to display synergism with piperacillin against β-lactamase producing strains.