623564-35-2

Basic information

• Product Name: 8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde,5,6-dihydro-(9CI)
• Synonyms: 8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde,5,6-dihydro-(9CI);6,8-dihydro-5H-imidazo[2,1-c][1,4]thiazine-2-carbaldehyde;5,6-dihydro-8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde
• CAS NO: 623564-35-2
• Molecular Formula: C₇H₈N₂OS
• Molecular Weight: 168.21622
• Product Categories: AMINETERTIARY
• Mol File: 623564-35-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde,5,6-dihydro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde,5,6-dihydro-(9CI)(623564-35-2)
• EPA Substance Registry System: 8H-Imidazo[2,1-c][1,4]thiazine-2-carboxaldehyde,5,6-dihydro-(9CI)(623564-35-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 623564-35-2(Hazardous Substances Data)

Upstream product

• 179685-20-2 3-Iminothiomorpholine hydrochloride 
• 19263-02-6 2-bromo-3-hydroxypropenal 

Downstream Products

• 623906-20-7 (5R)-6-[acetoxy-(5,6-dihydro-8H-imidazo[2,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester 

Relevant articles and documents

Bicyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors

This invention relates to certain bicyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. In accordance with the present invention there are provided compounds of general formula I or a pharmaceutically acceptable salt or in vivo hydrolyzable ester R5 thereof: wherein: One of A and B denotes hydrogen and the other an optionally substituted fused bicyclic heteroaryl group; and X═O or S.

Structure-activity relationship of 6-methylidene penems bearing 6,5 bicyclic heterocycles as broad-spectrum β-lactamase inhibitors: Evidence for 1,4-thiazepine intermediates with C7 R stereochemistry by computational methods

The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C β-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) β-lactamases and less so against the class B metallo-β-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallographic structures of a serine-bound reaction intermediate of 2 with SHV-1 (class A) and GC1 (class C) enzymes, compounds 14a-1 were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C β-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both β-lactamases, which is consistent with those obtained from the crystal structure of 2 with SHV-1 and GC1.

BICYCLIC 6-ALKYLIDENE-PENEMS AS ?-LACTAMASES INHIBITORS

The present invention provides a compound of Formula (I), pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.

PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES

The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.