74555-99-0

Basic information

• Product Name: 2H-1-Benzopyran-3-carboxamide, N-(4-bromophenyl)-2-oxo-
• CAS NO: 74555-99-0
• Molecular Formula: C16H10BrNO3
• Molecular Weight: 344.164
• Mol File: 74555-99-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-3-carboxamide, N-(4-bromophenyl)-2-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-3-carboxamide, N-(4-bromophenyl)-2-oxo-(74555-99-0)
• EPA Substance Registry System: 2H-1-Benzopyran-3-carboxamide, N-(4-bromophenyl)-2-oxo-(74555-99-0)

Safety Data

• Hazardous Substances Data: 74555-99-0(Hazardous Substances Data)

Upstream product

• 1846-76-0 ethyl coumarin-3-carboxylate 
• 106-40-1 4-bromo-aniline 
• 54396-25-7 N-phenyl-2-oxochromene-3-carboxamide 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 886124-83-0 C₁₃H₈N₂O₃ 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 95262-09-2 3-[(4-bromophenyl)amino]-3-oxopropanoic acid 
• 669000-20-8 methyl 3-((4-bromophenyl)amino)-3-oxopropanoate 

Downstream Products

• 76152-10-8 N-furfurylsalicylaldimine 
• 74556-08-4 N-(4-Bromo-phenyl)-N'-furan-2-ylmethyl-malonamide 
• 959-36-4 salicyaldehyde azine 
• 74556-03-9 N-(4-Bromo-phenyl)-2-hydrazinocarbonyl-acetamide 
• 74556-05-1 N-(2-Amino-ethyl)-N'-(4-bromo-phenyl)-malonamide 
• 94-93-9 N,N'-ethylenebis(salicylideneimine) 
• 2565-54-0 N-salicylidene-butylamine 
• 74556-07-3 N-(4-Bromo-phenyl)-N'-butyl-malonamide 
• 74556-15-3 N-(4-Bromo-phenyl)-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-14-2 N-(4-Bromo-phenyl)-2-[1-(2-hydroxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-16-4 N-(4-Bromo-phenyl)-2-[1-(4-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74568-56-2 N-(4-Bromo-phenyl)-2-[(E)-3-phenyl-prop-2-en-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-13-1 N-(4-Bromo-phenyl)-2-[1-phenyl-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 886-08-8 N-(benzyl)salicylaldimine 

Relevant articles and documents

Design, synthesis and in vitro evaluation of 2-oxo-n-substituted phenyl-2h-chromene-3-carboxamide derivatives as HIV integrase strand transfer inhibitors

Background: A series of eighteen 2-Oxo-N-substituted phenyl-2H-chromene-3-carboxamide analogues has been evaluated for HIV-1 integrase (IN) inhibition. Methods: The derivatives were synthesized via a two-step pathway commencing with 2-hydroxybenzaldehyde and diethyl malonate followed by hydrolysis of ester and coupling with various aromatic amines. The HIV-1 IN inhibitory potential of these compounds has been studied relative to dolutegravir, a known HIV-1 IN inhibitor using a standard available kit. Results: Six molecules (compounds 13h, 13i, 13l, 13p to 13r) showed significant inhibition of HIV-1 integrase 3′-strand transfer with IC50 values less than 1.7 μM. The presence of chromene-3-carboxamide motif was shown to be crucial for the enzymatic activity. In addition, molecular modelling studies were also done to justify the IN inhibition and in vitro-in silico correlation was drawn. Conclusion: However, these compounds did not show HIV-1 and HIV-2 inhibition below their cytotoxic concentration indicating that these compounds cannot be taken further for anti-HIV activity as such and require structural modification.

Coumarins and adenosine receptors: New perceptions in structure–affinity relationships

Adenosine receptor (AR) subtypes are involved in several physiological and pharmacological processes. Ligands that are able to selectively modulate one receptor subtype can delay or slow down the progression of diverse diseases. In this context, our research group focused its investigation into the discovery and development of novel, potent and selective AR ligands based on coumarin scaffold. Therefore, a series of 3-phenylcarboxamidocoumarins were synthesized and their affinity for the human AR subtypes was screened by radioligand binding assays for A1, A2A and A3 receptors and for A2B by adenylyl cyclase assay. Compound 26 was found to be the most remarkable, with a hA1/hA3 and hA2A/hA3 selectivity of 42, for the A3 AR (Ki?=?2.4?μm). Receptor-driven molecular modelling studies have provided valuable information on the binding/selectivity data of compound 26 and for the following optimization process. Moreover, compound 26 presents drug-like properties according to the general guidelines linked to the concept.

Synthesis and Reactions of Coumarin-3-N-bromoarylcarboxamides

Various coumarin-3-N-bromoarylcarboxamides (Ia-h) have been prepared and their reactions with aliphatic amines and hydrazines studied.Some acridinyl derivatives (XIa-f) of coumarin-3-carboxamide (Ii) have also been prepared.