623565-59-3

Basic information

• Product Name: 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro- (9CI)
• Synonyms: 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro- (9CI);6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine-2-carbaldehyde
• CAS NO: 623565-59-3
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15062
• Product Categories: ALDEHYDE
• Mol File: 623565-59-3.mol

Chemical Properties

• Boiling Point: 357.481 °C at 760 mmHg
• Flash Point: 169.999 °C
• Appearance: /
• Density: 1.417 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro- (9CI)(623565-59-3)
• EPA Substance Registry System: 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro- (9CI)(623565-59-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 623565-59-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is used as a pharmaceutical intermediate for the synthesis of various drug molecules. Its unique structure and properties allow it to serve as a key building block in the development of new therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
In the agrochemical industry, 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure enables the development of novel compounds with improved efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.
Used in Materials Science:
4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is employed in materials science for the development of advanced materials with specific properties. Its unique structure and functional groups can be exploited to create materials with tailored characteristics, such as improved mechanical strength, thermal stability, or optical properties, for use in various applications, including electronics, coatings, and sensors.
Further research and development into the synthesis and characterization of 4H-Pyrazolo[5,1-c][1,4]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) will help uncover its full potential and unlock new opportunities for its application in various industries.

Upstream product

• 623565-57-1 ethyl 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine-2-carboxylate 
• 623565-58-2 (6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methanol 

Downstream Products

• 623565-60-6 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant articles and documents

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 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.

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.

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.