1846-90-8

Basic information

• Product Name: N-benzyl-2-oxo-2H-chromene-3-carboxamide
• Synonyms: 2H-1-Benzopyran-3-carboxamide, 2-oxo-N-(phenylmethyl)-; N-Benzyl-2-oxo-2H-chromene-3-carboxamide
• CAS NO: 1846-90-8
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.29
• Mol File: 1846-90-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 569.8°C at 760 mmHg
• Flash Point: 298.4°C
• Density: 1.293g/cm³
• Vapor Pressure: 5.39E-13mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: N-benzyl-2-oxo-2H-chromene-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-2-oxo-2H-chromene-3-carboxamide(1846-90-8)
• EPA Substance Registry System: N-benzyl-2-oxo-2H-chromene-3-carboxamide(1846-90-8)

Safety Data

• Hazardous Substances Data: 1846-90-8(Hazardous Substances Data)

Upstream product

• 504-64-3 carbon suboxide 
• 886-08-8 N-(benzyl)salicylaldimine 
• 90-02-8 salicylaldehyde 
• 100-46-9 benzylamine 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 95-20-5 2-methyl-1H-indole 
• 21259-42-7 methyl 2-oxo-2H-chromene-3-carboxylate 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 15781-70-1 malonic acid bis-(2,4,6-trichloro-phenyl) ester 
• 3757-06-0 coumarin 3-carboxylic acid chloride 

Downstream Products

• 97095-03-9 N-Benzyl-6a,7,10,10a-tetrahydro-8,9-dimethyl-6-oxo-6H-5-oxaphenanthren-6a-carboxamid 

Relevant articles and documents

Synthesis, antiproliferative activities, and DNA binding of coumarin-3-formamido derivatives

Ten coumarin-3-formamido derivatives, N-benzyl-coumarin-3-carboxamide (2), N-fluorobenzyl-coumarin-3-carboxamide (3–5), N-methoxybenzyl-coumarin-3-carboxamide (6–8), N-((1-methyl-1H-imidazol-5-yl)methyl)-coumarin-3-carboxamide (9), N-(thiophen-2-ylmethyl)-coumarin-3-carboxamide (10), and N-(furan-2-ylmethyl)-coumarin-3-carboxamide (11), were synthesized and characterized. Compound 5 crystallizes in a monoclinic system P21/c space group with four chemical formulas in a unit cell; molecules of compound 5 are self-assembled into a two-dimensional supramolecular structure by intermolecular hydrogen bonds and C?C π stacking. The potential anticancer effects of these compounds on HeLa (cervical carcinoma), MCF-7 (breast), A549 (lung), HepG2 (liver), and human umbilical vein (HUVEC) cells were examined. Compared with compounds 1–8 and 10–11, compound 9 exhibits potent in vitro cytotoxicity against HeLa cells and lower cytotoxicity against normal cells. Therefore, further in-depth investigations of compound 9 were performed. Absorption titration experiments and fluorescence spectroscopy studies suggested that compound 9 binds to DNA through the intercalation mode.

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.

Synthesis and research of benzylamides of some isocyclic and heterocyclic acids as potential anticonvulsants

A series of benzylamides of isocyclic and heterocyclic acids was synthesized and tested in Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Near all synthesized derivatives of heterocyclic acids showed activity. All obtained derivatives of mono- and bicyclic isocyclic acids were inactive. The power of action of heterocyclic acids derivatives seems does not depend upon kind of heteroatom (N, O or S). One of the compounds (2-furoic acid benzylamide (4)) appeared most promising. It showed in minimal clonic seizure (6Hz) test (ASP) in rats after i. p. administration: MES ED50 = 36.5 mg/kg, TOX TD50 = 269.75 mg/kg, and PI = 7.39.