101156-40-5

Basic information

• Product Name: (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS NO: 101156-40-5
• Molecular Weight: 578.428
• Mol File: 101156-40-5.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(101156-40-5)
• EPA Substance Registry System: (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(101156-40-5)

Safety Data

• Hazardous Substances Data: 101156-40-5(Hazardous Substances Data)

Upstream product

• 104146-10-3 (6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 103-80-0 phenylacetyl chloride 
• 106773-36-8 4-methoxybenzyl-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride 

Downstream Products

• 143488-25-9 1-cyclopropyl-6-fluoro-7-{4-[2-(4-methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.3.0]oct-2-en-3-ylmethyl]-piperazin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1402070-26-1 C₂₈H₃₃N₅O₇S 
• 1412945-44-8 C₂₈H₃₁N₅O₇S 
• 1412945-45-9 C₃₂H₃₄N₈O₇S 
• 1412945-46-0 C₃₄H₃₆N₆O₇S 
• 1402070-25-0 C₂₀H₂₅N₅O₆S 
• 1412945-50-6 C₂₄H₂₆N₈O₆S 
• 1402070-27-2 C₂₀H₂₄N₅O₆S^(1-)*K⁽¹⁺⁾ 
• 1412945-53-9 C₂₀H₂₂N₅O₆S^(1-)*K⁽¹⁺⁾ 
• 1413936-09-0 C₂₄H₂₅N₈O₆S^(1-)*K⁽¹⁺⁾ 

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.

Metal β - lactamase inhibitor cyclic amino dithio carboxylic acid salt derivative and its preparation method

The invention belongs to the field of medicinal chemistry, in particular to a metal β - lactamase inhibitor cyclic amino dithio carboxylic acid salt derivative and its preparation method, The invention through a low-temperature reaction and the combined effect of the alkali catalyst, and effectively increases the 7 - phenylacetylamino - 3 - chloromethyl - 4 - cephalosporanic acid-methoxybenzyl ester yield.

A Self-Immobilizing and Fluorogenic Probe for β-Lactamase Detection

The spread of antibiotic resistance in pathogenic bacteria has become one of the major concerns to public health. Improved monitoring of drug resistance is of high importance for infectious disease control. One of the major mechanisms for bacteria to overcome treatment of antibiotics is the production of β-lactamases, which are enzymes that hydrolyze the β-lactam ring of the antibiotic. In this study, we have developed a self-immobilizing and fluorogenic probe for the detection of β-lactamase activity. This fluorogenic reagent, upon activation by β-lactamases, turns on a fluorescence signal and, more importantly, generates a covalent linkage to the target enzymes or the nearby proteins. The covalent labeling of enzymes was confirmed by SDS-PAGE analysis and MALDI-TOF mass spectrometry. The utility of this structurally simple probe was further confirmed by the fluorescent labeling of a range of β-lactamase-expressing bacteria.