623565-63-9

Usage

Uses

Used in Organic Synthesis:
5H-Pyrazolo[5,1-b][1,3]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is used as a key intermediate in various organic synthesis reactions. Its carboxaldehyde group allows for the formation of various functional groups, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
5H-Pyrazolo[5,1-b][1,3]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is used as a reagent in the pharmaceutical industry for the development of new drugs. Its unique chemical structure and properties make it a promising candidate for the synthesis of bioactive compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5H-Pyrazolo[5,1-b][1,3]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is used as a building block for the design and synthesis of novel compounds with potential medicinal properties. Its versatile chemical structure allows for the exploration of various chemical modifications to enhance the biological activity and selectivity of the synthesized compounds.
Used in Drug Discovery:
5H-Pyrazolo[5,1-b][1,3]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is employed in drug discovery processes to identify and optimize lead compounds with potential therapeutic effects. Its unique chemical features make it a valuable tool for the development of new drugs targeting various diseases and conditions.
Used in Chemical Research:
In chemical research, 5H-Pyrazolo[5,1-b][1,3]oxazine-2-carboxaldehyde, 6,7-dihydro(9CI) is utilized as a model compound to study the reactivity and properties of pyrazolo[5,1-b][1,3]oxazine derivatives. This helps researchers gain insights into the structure-activity relationships and the potential applications of these compounds in various fields.

Upstream product

• 153597-59-2 ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3 ]oxazine-2-carboxylate 
• 623565-62-8 (6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methanol 

Downstream Products

• 623565-64-0 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant academic research and scientific papers

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.

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.