Synthesis and Anti‐influenza Virus Activity of Novel bis(4H‐chromene‐3‐carbonitrile) Derivatives

Abstract

An efficient and convenient method for the synthesis of bis(4H‐chromene‐3‐carbonitrile) derivatives by one‐pot, multicomponent reaction of bis‐aldehydes, malononitrile, and dimedone in the presence of a catalytic amount of piperidine is reported. Bis(2‐benzylidene‐1H‐indene)‐1,3‐(2H)‐dione derivatives were obtained as the main products as a result of reaction of the bis(arylidenemalononitriles) with indandione. The anti‐influenza H5N1 virus activities of the newly prepared bis‐chromene derivatives are also investigated.

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

“…Due to their vast pharmacological profile, the nitrogen and sulfur‐containing heterocycles present an important class in the life science industry and drug research areas . Among them, urea derivatives constitute the core structural element of many biologically active molecules such as Sorafenib and larotrectinib (VITRAKVI) which has urea moiety in its structure as shown in Figure .…”

3‐Amino‐5‐cyanomethylpyrazole‐4‐carbonitrile: Versatile Reagent for Novel Bis(pyrazolo[1,5‐a]pyridine) Derivatives via a Multicomponent Reaction

“…In a preliminary trial, we studied the reaction of 3‐amino‐5‐(cyanomethyl)‐1 H ‐pyrazole‐4‐carbonitrile 4 with bis‐arylidenemalononitrile derivatives 3 (which is formed in situ upon reaction of bis‐aldehyde 1 with malononitrile 2 ) in dioxane in the presence of a catalytic amount of piperidine (method A). Mechanistically, three possible products are expected for this reaction, namely, bis(7‐amino‐2‐(cyanomethyl)pyrazolo[1,5‐ a ]pyrimidine‐3,6‐dicarbonitrile) 5 , bis(3,4‐diamino‐1 H ‐indazole‐5,7‐dicarbonitrile) 6 , or bis(4,1‐phenylene)bis(2,7‐diaminopyrazolo[1,5‐ a ]pyridine‐3,4,6‐tricarbonitrile) 7 (Schemes and , pathways A, B, or C).…”

“…In view of the aforementioned facts and as part of our research interest in both bis‐heterocycles and the Michael addition reaction using substituted cinnamonitrile derivatives , we report herein the results of our investigations concerning the reactivity pattern of 3‐amino‐5‐(cyanomethyl)‐1 H ‐pyrazole‐4‐carbonitrile 4 towards bis‐cinnamonitrile derivatives 3 .…”

Bis(enaminones) as Versatile Precursors for Novel Bis([1,2,4]triazolo[1,5‐a]pyrimidines) and Bis(2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1H)‐ones)

“…In the last decades, our group has been heavily involved in a program aiming at exploring the synthetic potentiality of functionally substituted enamines . In continuation to this work, and in conjunction to our interest in the chemistry of bis(heterocycles) , we report herein on the reactivity patterns of enamines towards 1 H ‐1,2,4‐triazol‐5‐amine and 6‐amino‐2‐thioxopyrimidin‐4‐one.…”