Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities

Condensation of 3-N,N-diethylaminophenol (1) with α-cyanocinnamonitriles (2a–c) and ethyl α-cyanocinnamates (2d–f) provided compounds 3a–f and 4a–c. 12H-Chromeno[2,3-d]pyrimidine derivatives 6, 11–13 and 16 were obtained by treatment of 4H-chromene compounds (3) with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, UV, 1H NMR, 13C NMR and MS data. Some of the new compounds were evaluated for antimicrobial and cytotoxicity activities.

Condensation of 3-N,N-diethylaminophenol (1) with various substituted α-cyanocinnamonitriles (2a–c) in ethanolic piperidine afforded 3a–c, while condensation of 3-N,N-diethylaminophenol (1) with ethyl α-cyanocinnamate (2d–f) in ethanolic piperidine afforded in addition to ethyl 2-amino-4-(4-halophenyl)-7-(diethylamino)-4H-chromene-3-carboxylate (3d–f), the 4-(4-halophenyl)-7-(diethylamino)-coumarin-3-carbonitrile (4a–c).Figure optionsDownload as PowerPoint slideResearch highlights
► In this paper we report the synthesis of 4H-chromene, coumarin and chromeno[2,3-d]-pyrimidine derivatives and examine the antimicrobial; antitumor activities of some of this novel series.
► Structures of the synthesized compounds were elucidated on the basis of IR, 1H NMR, 13C NMR and MS data.
► The preliminary in vitro antimicrobial activity has demonstrated that the chromeno[2,3-d]pyrimidine derivatives are more active than 4H-chromene and coumarin derivatives.
► The cytotoxicity evalution using viability assays and the inhibitory activities demonstrates that compound 3a had the most prominent activity against the human breast tumor cells (MCF-7) and human lung cancer cells (HCT).
► This neoplastic cells growth inhibition could be attributed to the presence of the chloro atom in the 4-position of the phenyl ring in combination with the cyano group in the 3-position in 4H-chromene.