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Novel β-enaminonitrile/ester compounds (4, 6) and an imidate of 4 (9) were utilized as key scaffolds for the synthesis of newly 2-substituted 4H-benzo[h]chromene (7, 8, 10, 11, 13, 14) and 7H-benzo[h]chromeno[2,3-d]pyrimidine derivatives (15-19). The spectral data confirmed the successful isolation of the desired compounds. The targeted compounds were assessed for their in vitro anticancer activity against mammary gland breast cancer cell line (MCF-7), human colon cancer (HCT-116), and liver cancer (HepG-2), while doxorubicin, vinblastine, and colchicine were utilized as standard references drugs. Some of the examined compounds displayed high growth inhibitory activity against the three different cell lines. For example, the aminoimino derivative (18) exhibited excellent antitumor activity versus all cancer cell lines with IC 50 values = 0.45 µg/mL, 0.7 µg/mL, and 1.7 µg/mL. Among the tested molecules, compounds 9, 15, and 18 were selected for further study regarding their effects on cell cycle analysis, apoptosis assay, caspase 3/7 activity, and DNA fragmentation. We found that these three potent cytotoxic compounds induce cell cycle arrest at the S and G2/M phases, which causes apoptosis. Furthermore, these compounds significantly inhibit the invasion and migration of the different tested cancer cells. Finally, the SAR survey highlighted the antitumor activity of the new molecules that was remarkably influenced by the hydrophilicity of substituent as well the fused rings at certain positions., (Copyright © 2019 Elsevier Inc. All rights reserved.)

Novel fused chromenes ( 4 , 7 ⁻ 11 ) and pyrimidines ( 12 ⁻ 16 ) were designed, synthesized, and evaluated for their mammary gland breast cancer (MCF-7), human colon cancer (HCT-116), and liver cancer (HepG-2) activities. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR, and mass spectroscopy. The preliminary results of the bioassay disclosed that some of the target compounds were proven to have a significant antiproliferative effect against the three cell lines, as compared to Doxorubicin, Vinblastine, and Colchicine, used as reference drugs. Particularly, compounds 7 and 14 exerted promising anticancer activity towards all cell lines and were chosen for further studies, such as cell cycle analysis, cell apoptosis, caspase 3/7 activity, DNA fragmentation, cell invasion, and migration. We found that these potent cytotoxic compounds induced cell cycle arrest at the S and G2/M phases, prompting apoptosis. Furthermore, these compounds significantly inhibit the invasion and migration of the different tested cancer cells. The structure-activity relationship (SAR) survey highlights that the antitumor activity of the desired compounds was affected by the hydrophobic or hydrophilic nature of the substituent at different positions.

Background: Synthetic azo compounds and their derivatives have been studied extensively due to their biological and pharmacological activities. Pyranopyridines, pyranopyrimidines and tetrazoles derivatives have emerged as a promising and attractive scaffold in the development of potent biological and pharmacological agents., Objectives: To design a series of new benzochromeno(pyridine/pyrimidine/tetrazole) derivatives and evaluate their antimicrobial activity against some bacterial strains (Gram-positive and Gram-negative) and some fungal strains., Materials and Methods: The (E)-7-(4-chlorophenyl)-5-(phenyldiazenyl)-10-thioxo-7,9,10,11-tetrahydro-8Hnaptho[ 1,2-b]pyrano[2,3-d]pyrimidin-8-one (4) was synthesized by the reaction of 4H-naphtho[1,2-b]pyran-3- carbonitrile (3) with carbon disulfide in alcoholic potassium hydroxide solution. Reaction of 3 with sodium azide in DMF and in presence of ammonium chloride afforded 6-(phenyldiazenyl)-3-(1H-tetrazol-5-yl)-4Hbenzo[ h]chromen-2-amine (7) while with malononitrile, thiourea or urea gave chromeno[2,3-b]pyridine-9- carbonitrile (8), chromeno[2,3-d]pyrimidine-10-thione (9) and chromeno[2,3-d]pyrimidin-10-one (10), respectively. The assignment structures were established on the basis of spectral data., Results: In this study, the antimicrobial activity of the synthesized compounds 3-12 was examined for their in vitro antimicrobial activity by using agar diffusion method such as Mueller-Hinton agar medium for bacteria and Sabouraud's agar medium for fungi. Ampicillin and mycostatine were included in the experiments as reference drugs., Conclusion: A series of new benzochromeno(pyridine/pyrimidine/tetrazole) derivatives were synthesized in this work. All compounds were evaluated in antimicrobial activities., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

A series of 1H-benzo[f]chromene-2-carbonitriles was synthesized and evaluated for their cytotoxic activities against MCF-7, HCT-116, and HepG-2 cancer cells. The SAR studies reported that the substitution in the phenyl ring at 1-position of 1H-benzo[f]chromene nucleus with the specific group, H atom, or methoxy group at 9-position increases the ability of the molecule against the different cell lines.

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., (Copyright © 2010 Elsevier Masson SAS. All rights reserved.)