1436862-03-1

Basic information

• Product Name: trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester
• Synonyms: trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester
• CAS NO: 1436862-03-1
• Molecular Weight: 487.556
• Mol File: 1436862-03-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester(1436862-03-1)
• EPA Substance Registry System: trans-3-[N'-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester(1436862-03-1)

Safety Data

• Hazardous Substances Data: 1436862-03-1(Hazardous Substances Data)

Upstream product

• 192214-06-5 (R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid 
• 1217655-90-7 (R)-methyl-1-benzyloxycarbonyl-pyrrolidine-3-carboxylate 
• 441717-40-4 (R)-methyl-1-tert-butoxycarbonyl-pyrrolidine-3-carboxylate 
• 99735-47-4 (3R)-1-[(R)-1-phenylethyl]-3-(hydroxymethyl)pyrrolidine 
• 1407997-80-1 tert-butyl (R)-3-(hydrazinecarbonyl)pyrrolidine-1-carboxylate 
• 192214-05-4 benzyl (R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 208519-98-6 (S)-ethyl 2-(((tert-butoxy)carbonyl)amino)-6-diazo-5-oxohexanoate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 1416134-63-8 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 72925-16-7 (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 
• 1463501-46-3 (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 77925-80-5 N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine 

Relevant articles and documents

Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234

Limited treatment options exist to combat infections caused by multidrug-resistant (MDR) Gram-negative bacteria possessing broad-spectrum β-lactamases. The design of novel β-lactamase inhibitors is of paramount importance. Here, three novel diazabicyclooctanes (DBOs), WCK 5153, zidebactam (WCK 5107), and WCK 4234 (compounds 1-3, respectively), were synthesized and biochemically characterized against clinically important bacteria. Compound 3 inhibited class A, C, and D β-lactamases with unprecedented k2/K values against OXA carbapenemases. Compounds 1 and 2 acylated class A and C β-lactamses rapidly but not the tested OXAs. Compounds 1-3 formed highly stable acyl-complexes as demonstrated by mass spectrometry. Crystallography revealed that 1-3 complexed with KPC-2 adopted a "chair conformation" with the sulfate occupying the carboxylate binding region. The cefepime-2 and meropenem-3 combinations were effective in murine peritonitis and neutropenic lung infection models caused by MDR Acinetobacter baumannii. Compounds 1-3 are novel β-lactamase inhibitors that demonstate potent cross-class inhibition, and clinical studies targeting MDR infections are warranted.

1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS

β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.