307313-06-0

Basic information

• Product Name: Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI)
• Synonyms: Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI);4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carbaldehyde;4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxaldehyde
• CAS NO: 307313-06-0
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.1778
• Product Categories: ALDEHYDE
• Mol File: 307313-06-0.mol

Chemical Properties

• Boiling Point: 321.356 °C at 760 mmHg
• Flash Point: 148.151 °C
• Appearance: /
• Density: 1.284 g/cm³
• PKA: 0.59±0.20(Predicted)
• CAS DataBase Reference: Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI)(307313-06-0)
• EPA Substance Registry System: Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI)(307313-06-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 307313-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro(9CI) is used as a key intermediate in the synthesis of new drugs and bioactive molecules. Its unique structure and properties make it a promising candidate for the development of innovative therapeutic agents.
Used in Drug Discovery and Development:
Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro(9CI) serves as a valuable building block in medicinal chemistry for the design and synthesis of novel drug candidates. Its heterocyclic nature and functional groups provide opportunities for further chemical modifications, enhancing its potential as a versatile scaffold in drug discovery.
Used in Research and Development:
Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro(9CI) is utilized in scientific research to explore its chemical properties, reactivity, and potential interactions with biological targets. This knowledge can contribute to the understanding of its therapeutic potential and guide the development of new applications in medicine and related fields.

Upstream product

• 623564-49-8 (4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)methanol 
• 307307-84-2 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester 
• 105786-95-6 4,5,6,7-tetrahydro<1.2.3>oxadiazolo<3,4-a>pyridin-3-one 
• 4515-18-8 1-nitroso-piperidine-2-carboxylic acid 
• 4043-87-2 pipecolic Acid 
• 1052103-62-4 1-[4-(phenylselanyl)butyl]-1H-pyrazole-3-carbaldehyde 

Downstream Products

• 1025959-41-4 6-[acetoxy-(4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 

Relevant articles and documents

Bu3SnH-mediated radical cyclisation onto azoles

Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-, (TMS)3SiH- and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the?rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate aromatic homolytic substitution in which the initiator or breakdown products from the inhibitor are responsible for the H-abstraction step.

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.

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.