118055-06-4

Basic information

• Product Name: ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate
• Synonyms: ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate
• CAS NO: 118055-06-4
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23036
• Mol File: 118055-06-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate(118055-06-4)
• EPA Substance Registry System: ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate(118055-06-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 118055-06-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate is used as a synthetic intermediate for the development of complex chemical structures. Its specific structure allows for the creation of new compounds with potential therapeutic applications, contributing to the advancement of drug discovery and design.
Used in Chemical Industry:
Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylate is employed as a synthetic intermediate in the synthesis of various chemical products. Its role in the formation of more complex structures is crucial for the production of a wide range of chemical compounds, enhancing the versatility and applicability of this intermediate in different chemical processes.

Upstream product

• 16205-44-0 Pyrazolo<1,5-a>pyridin-3-carbonsaeureethylester 
• 4515-18-8 1-nitroso-piperidine-2-carboxylic acid 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 132910-79-3 (+/-) methyl N-tert-butyloxycarbonyl 2-piperidinecarboxylate 
• 105786-95-6 4,5,6,7-tetrahydro<1.2.3>oxadiazolo<3,4-a>pyridin-3-one 
• 623-47-2 propynoic acid ethyl ester 
• 4043-87-2 pipecolic Acid 
• 1334403-02-9 C₁₆H₂₇BN₂O₄ 
• 121193-65-5 tetrahydropyridino[1,2-c][1,2,3]oxadiazolone 
• 37622-90-5 4-ethoxycarbonylpyrazole 

Downstream Products

• 1367714-09-7 C₂₀H₂₄F₂N₄O 
• 307307-97-7 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid 
• 132255-62-0 Methyl-3-(4-benzyloxymethyl-4,5,6,7-tetrahydropyrazolo<1,5-a>pyridine-3-yl)-3-oxo-propionate 

Relevant articles and documents

Design, synthesis and biological evaluation of ring-fused pyrazoloamino pyridine/pyrimidine derivatives as potential FAK inhibitors

We report herein the synthesis of novel ring-fused pyrazoloamino pyridine/pyrimidine derivatives as potential FAK inhibitors and the evaluation of pharmaceutical activity against five cancer cell lines (MDA-MB-231, BXPC-3, NCI-H1975, DU145 and 786O). Generally, the majority of compounds displayed strong anti-FAK enzymatic potencies (IC50 1 nM) and could effectively inhibit several class of cancer cell lines within the concentration of 3 μM in comparison with GSK2256098 as a reference. Among them, compound 4o is considered to be the most effective due to high sensitivity in antiproliferation. In culture, 4o could not only inhibit FAK Y397 phosphorylation in MDA-MB-231 cell line, but also trigger apoptosis in a dose-dependent manner. Furthermore, computational docking analysis also suggested that 4o and TAE-226 displayed the similar interaction with FAK kinase domain.

A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments

An efficient hydrogenation protocol under continuous flow conditions was developed for the synthesis of underrepresented semi-saturated bicyclic fragments containing highly sp3-rich skeletons for fragment-based drug discovery (FBDD) programs. Excellent yields were generally achieved by using Pd/C (10 % w/w) and RaNi at 25–150 °C under 4–100 bar of hydrogen pressure. The generated fragments, with appropriate physicochemical properties, present diverse hydrogen-bonding pharmacophores and useful vectors for their synthetic elaboration in the optimization stage. Successive, simple functionalizations in continuous flow were accomplished to demonstrate the opportunity to develop multi-step continuous flow synthesis of valuable starting points for FBDD campaigns. A conclusive quality control (QC) was essential to discard those structures which do not fit the typical fragment library parameters.

Focal adhesion kinase inhibitor and use

The invention belongs to the field of medicines, relates to a focal adhesion kinase inhibitor and use, in particular relates to a novel focal adhesion kinase inhibitor compound, or stereoisomers, geometric isomers, tautomers, oxynitrides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, further relates to the use of the compound and pharmaceutical compositions as medicines, in particular the use of the compound and pharmaceutical compositions in manufacture of medicines for treatment or prevention of cancer, pulmonary hypertension, and pathological angiogenesis-related diseases.

Identification of fused bicyclic heterocycles as potent and selective 5-HT2A receptor antagonists for the treatment of insomnia

A series of fused bicyclic heterocycles was identified as potent and selective 5-HT2A receptor antagonists. Optimization of the series resulted in compounds that had improved PK properties, favorable CNS partitioning, good pharmacokinetic properties, and significant improvements on deep sleep (delta power) and sleep consolidation.

Practical radical cyclizations with arylboronic acids and trifluoroborates

Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and in a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.

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.

Radical cyclisation onto pyrazoles: Synthesis of withasomnine

A novel synthetic protocol for the synthesis of [1,2-b]-fused bicyclic pyrazoles has been developed using radical cyclisation. The protocol uses cyclisation of pyrazole-1-(ω-alkyl) radicals generated from 1-[ω-(phenylselenyl)alkyl]-pyrazole precursors. The pyrazole natural product, withasomnine (3-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole), and larger ring analogues have been synthesised in good yield using the protocol. A Bu3SnH-mediated oxidative cyclisation mechanism is facilitated by azo or Et3B radical initiators acting as oxidants of the intermediate π-radicals.