1309605-97-7

Basic information

• Product Name: 4-[3-(3-chloro-4-methoxyphenyl)-1H-pyrazol-4-yl] pyridine
• Synonyms: 4-[3-(3-chloro-4-methoxyphenyl)-1H-pyrazol-4-yl] pyridine
• CAS NO: 1309605-97-7
• Molecular Weight: 285.733
• Mol File: 1309605-97-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-[3-(3-chloro-4-methoxyphenyl)-1H-pyrazol-4-yl] pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[3-(3-chloro-4-methoxyphenyl)-1H-pyrazol-4-yl] pyridine(1309605-97-7)
• EPA Substance Registry System: 4-[3-(3-chloro-4-methoxyphenyl)-1H-pyrazol-4-yl] pyridine(1309605-97-7)

Safety Data

• Hazardous Substances Data: 1309605-97-7(Hazardous Substances Data)

Upstream product

• 37908-96-6 3-chloro-4-methoxy benzoic acid 
• 51-44-5 3,4-dichlorbenzoic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 1309606-06-1 3-(3-chloro-4-methoxyphenyl)-4-(pyridin-4-yl)-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazole-1-carboxamide 
• 1309606-04-9 3-(3-chloro-4-methoxyphenyl)-N-(2-(piperidin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-00-5 3-(3-chloro-4-methoxyphenyl)-N-(2-morpholinoethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-02-7 3-(3-chloro-4-methoxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-03-8 N-(2-(4-acetylpiperazin-1-yl)ethyl)-3-(3-chloro-4-methoxyphenyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-07-2 3-(3-chloro-4-hydroxyphenyl)-N-(2-(dimethylamino)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-08-3 3-(3-chloro-4-hydroxyphenyl)-N-(2-(diethylamino)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-09-4 3-(3-chloro-4-hydroxyphenyl)-N-(2-morpholinoethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-10-7 3-(3-chloro-4-hydroxyphenyl)-N-(2-(2,6-dimethylmorpholino)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-11-8 3-(3-chloro-4-hydroxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-12-9 N-(2-(4-acetylpiperazin-1-yl)ethyl)-3-(3-chloro-4-hydroxyphenyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-13-0 3-(3-chloro-4-hydroxyphenyl)-N-(2-(piperidin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-14-1 3-(3-chloro-4-hydroxyphenyl)-N-(2-(2-methylpiperidin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide 
• 1309606-15-2 3-(3-chloro-4-hydroxyphenyl)-4-(pyridin-4-yl)-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazole-1-carboxamide 

Relevant articles and documents

Discovery of a potent p38α/MAPK14 kinase inhibitor: Synthesis, in vitro/in vivo biological evaluation, and docking studies

This article reports the synthesis of new triarylpyrazole derivatives possessing urea or amide linker, and their biological activities at molecular, cellular, and in vivo levels. Compound 2b was the most potent inhibitor of p38α/MAPK14 kinase (IC50 = 22 nM) among this series. Molecular docking studies were conducted to understand the kinase inhibitory variations and the basis of selectivity. Compound 2b was able to inhibit p38α/MAPK14 kinase inside HEK293 cells in nanoBRET cellular kinase assay with EC50 value of 0.55 μM, comparable to the potency of dasatinib. Compound 2b inhibited TNF-α production in lipopolysaccharide-induced THP-1 cells with IC50 value of 58 nM. In addition, compound 2b showed low potency against hERG. It is 622.38 times less potent than E?4031 against hERG, so the risk of cardiotoxicity of the compound is very minimal. Compound 2b showed also high plasma stability in vitro in human and rat plasmas. The in vivo PK profile of compound 2b is acceptable, and its antiinflammatory effect was comparable to diclofenac with no ulcerogenic side effect on stomach.

Antiproliferative diarylpyrazole derivatives as dual inhibitors of the ERK pathway and COX-2

A series of 3,4-diarylpyrazole-1-carboxamide derivatives was designed and synthesized. A selected group of the target compounds was tested for in vitro antiproliferative activities over a panel of 60 cancer cell lines at the National Cancer Institute (NCI, Bethesda, MD, USA) at a single-dose concentration of 10 μm, and the four most active compounds 9a, 9l, 9n, and 10o were further tested in a five-dose testing mode to determine their IC50 values over the 60 cell lines. In addition, a selected group of target compounds were tested for inhibitory effect over cyclooxygenase isozymes. Compounds 9a, 9l, 9n, and 10o were also tested for MEK and ERK kinase inhibitory activity using Western blot assay. Compound 10o was selective toward melanoma cell line subpanel, and its antiproliferative activity may be attributed to selective cyclooxygenase-2 inhibition and ERK pathway inhibition.

Design and synthesis of 3-(3-chloro-4-substituted phenyl)-4-(pyridin-4-yl)- 1Hpyrazole- 1-carboxamide derivatives and their antiproliferative activity against melanoma cell line

Design and synthesis of new 3,4-diarylpyrazole-1-carboxamide derivatives are described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the synthesized compounds showed moderate activity against A375, compared with Sorafenib. On the other hand, compounds Ia, Ie, IIb, and IIh were more potent than Sorafenib. In addition, compound IIa was equipotent to Sorafenib. Among all of these derivatives, compound IIb which has diethylamino and phenolic moieties showed the most potent antiproliferative activity against A375 human melanoma cell line. Virtual screening was carried out through docking of the most potent compound IIb into the domain of V600E-b-Raf and the binding mode was studied. Copyright