27255-72-7

Basic information

• Product Name: 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid
• Synonyms: 7-(Phenylacetamido)deacetoxycephalo-aporanicacid;(6R-trans)-3-Methyl-8-oxo-7-(phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-PHENYL-ACETAMIDO-DEACETOXY-CEPHALOSPORANIC-ACID;4-METHYL-7-OXO-8-(2-PHENYLACETYL)AMINO-2-THIA-6-AZABICYCLO[4.2.0]OCT-4-ENE-5-CARBOXYLIC ACID;phenylacetyl 7-aminodesacetoxycephalosporanic acid;(6R-7-Trans)-3-methyl-8-oxo-7-[(Phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic;(6R,6β)-3-Methyl-8-oxo-7β-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7S)-3-Methyl-8-oxo-7β-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS NO: 27255-72-7
• Molecular Formula: C₁₆H₁₆N₂O₄S
• Molecular Weight: 332.38
• EINECS: 248-379-3
• Mol File: 27255-72-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 707.7°C at 760 mmHg
• Flash Point: 381.8°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 5.08E-21mmHg at 25°C
• Refractive Index: 1.679
• PKA: 3.13±0.50(Predicted)
• CAS DataBase Reference: 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid(27255-72-7)
• EPA Substance Registry System: 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid(27255-72-7)

Safety Data

• Hazardous Substances Data: 27255-72-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H16N2O4S/c1-9-8-23-15-12(14(20)18(15)13(9)16(21)22)17-11(19)7-10-5-3-2-4-6-10/h2-6,12,15H,7-8H2,1H3,(H,17,19)(H,21,22)/t12-,15-/m0/s1

Upstream product

• 859-07-4 cephaloram 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 103-80-0 phenylacetyl chloride 
• 4052-54-4 Penicillin G 1-(s)-oxide 
• 80127-23-7 allyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 80127-25-9 (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester 
• 76627-82-2 2-chloro-2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate 
• 113-98-4 Penicillin G potassium 
• 37794-96-0 7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid 
• 80127-26-0 2-chloro-2-propenyl (6R,7R)-3-methyl-7-(phenylacetamido)-8-oxo-3-cephem-4-carboxylate 
• 65111-56-0 (6R)-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid benzhydrylidene-methyl-hydrazide 

Downstream Products

• 34708-39-9 (6R)-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 33465-36-0 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid methyl ester 
• 941598-47-6 cephalosporin G 2-(dimethylamino)ethyl ester 
• 54011-14-2 acetoxymethyl 7β-phenylacetamido-3-methyl-3-cephem-4-carboxylate 
• 941598-52-3 C₁₆H₁₅O₃N₂SF 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 103-82-2 phenylacetic acid 

Relevant articles and documents

Novel Cephalosporin Conjugates Display Potent and Selective Inhibition of Imipenemase-Type Metallo-β-Lactamases

In an attempt to exploit the hydrolytic mechanism by which β-lactamases degrade cephalosporins, we designed and synthesized a series of novel cephalosporin prodrugs aimed at delivering thiol-based inhibitors of metallo-β-lactamases (MBLs) in a spatiotemporally controlled fashion. While enzymatic hydrolysis of the β-lactam ring was observed, it was not accompanied by inhibitor release. Nonetheless, the cephalosporin prodrugs, especially thiomandelic acid conjugate (8), demonstrated potent inhibition of IMP-type MBLs. In addition, conjugate 8 was also found to greatly reduce the minimum inhibitory concentration of meropenem against IMP-producing bacteria. The results of kinetic experiments indicate that these prodrugs inhibit IMP-type MBLs by acting as slowly turned-over substrates. Structure-activity relationship studies revealed that both phenyl and carboxyl moieties of 8 are crucial for its potency. Furthermore, modeling studies indicate that productive interactions of the thiomandelic acid moiety of 8 with Trp28 within the IMP active site may contribute to its potency and selectivity.

CEPHALOSPORIN-TYPE COMPOUNDS

The present technology is directed to compounds, compositions, and methods related to the treatment of bacterial and fungal infections. The compounds are of Formula I or stereoisomers, tautomers, solvates, and/or pharmaceutically acceptable salts thereof. The present technology is especially well-suited for use in treating non-replicating Mycobacterium tuberculosis.

De-esterification process

An efficient process for de-esterification has been provided for by application of special tetrahalogenides. By applying this process a new compound, viz. cefesone, and especially the E-isomer thereof, has been prepared.