1847-01-4

Basic information

• Product Name: N-(3-chlorophenyl)-2-oxo-2H-chromene-3-carboxamide
• Synonyms: N-(3-chlorophenyl)-2-oxo-2H-chromene-3-carboxamide
• CAS NO: 1847-01-4
• Molecular Formula: C₁₆H₁₀ClNO₃
• Molecular Weight: 299.7085
• Mol File: 1847-01-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(3-chlorophenyl)-2-oxo-2H-chromene-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chlorophenyl)-2-oxo-2H-chromene-3-carboxamide(1847-01-4)
• EPA Substance Registry System: N-(3-chlorophenyl)-2-oxo-2H-chromene-3-carboxamide(1847-01-4)

Safety Data

• Hazardous Substances Data: 1847-01-4(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 886124-83-0 C₁₃H₈N₂O₃ 
• 108-42-9 3-chloro-aniline 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 1846-76-0 ethyl coumarin-3-carboxylate 

Relevant articles and documents

Mapping Chromone-3-Phenylcarboxamide Pharmacophore: Quid Est Veritas?

Chromone-3-phenylcarboxamides (Crom-1 and Crom-2) were identified as potent, selective, and reversible inhibitors of human monoamine oxidase B (hMAO-B). Since they exhibit some absorption, distribution, metabolism, and excretion (ADME)-toxicity liabilities, new derivatives were synthesized to map the chemical structural features that compose the pharmacophore, a process vital for lead optimization. Structure-activity relationship data, supported by molecular docking studies, provided a rationale for the contribution of the heterocycle's rigidity, the carbonyl group, and the benzopyran heteroatom for hMAO-B inhibitory activity. From the study, N-(3-chlorophenyl)-4H-thiochromone-3-carboxamide (31) (hMAO-B IC50 = 1.52 ± 0.15 nM) emerged as a reversible tight binding inhibitor with an improved pharmacological profile. In in vitro ADME-toxicity studies, compound 31 showed a safe cytotoxicity profile in Caco-2, SH-SY5Y, HUVEC, HEK-293, and MCF-7 cells, did not present cardiotoxic effects, and did not affect P-gp transport activity. Compound 31 also protected SH-SY5Y cells from iron(III)-induced damage. Collectively, these studies highlighted compound 31 as the first-in-class and a suitable candidate for in vivo preclinical investigation.

Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives

A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the compounds 4a, 4d, 4e and 4f, EC50 values of which against Rhizoctorzia solani were as low as 1.80 μg/mL, 2.50 μg/mL, 2.25 μg/mL and 2.10 μg/mL, respectively, exhibiting more effective control with that of the positive control than Boscalid. Furthermore, compounds 4a and 4e represented equivalent antifungal activity with Boscalid against Botrytis cinerea.