Abstract
Several 4H-pyrano[3,2-h]quinoline 3,4,7-9, 7H-pyrimido[4',5':6,5]pyrano[3,2-h]quinoline 10a,b and 14Hpyrimido[ 4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline 11a-c derivatives were obtained by treatment of (E) 2-(4- chlorostyryl)-8-hydroxyquinoline 1, (E) 2-amino-4-(4-chlorophenyl)-9-(4-chlorostyryl)-4H-pyrano[3,2-h]quinoline-3- carbonitr-ile 3 or (E) 9-amino-7-(4-chlorophenyl)-2-(4-chlorostyryl)-8-imino-8,9-dihydro-7H-pyrimido-[4',5':6,5]pyrano [3,2-h]quinoline 10b with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR-DEPT, 13C NMR-APT and MS data. The antitumor activity of the synthesized compounds was investigated and compared with that of the standard drug vinblastine, a well-known anticancer drug, using MTT colorimetric assay. Among them, compounds 10b and 3 showed the most potent activity against the human breast tumor cells (MCF-7) and the human lung carcinoma cells (HCT), while compound 10b exhibited the most potent activity against the human hepatocellular carcinoma cells (HepG-2). The structure-activity relationships are discussed
Keywords: HIV integrase, anti-proliferative effects, styrylquinoline derivatives, quinoline nucleus, benzaldehyde, HCT, IR spectrum, S.pyogens
Letters in Drug Design & Discovery
Title:Synthesis and Antitumor Activities of 4H-Pyrano[3,2-h]quinoline-3-carbonitrile, 7H-Pyrimido[4',5':6,5]pyrano[3,2-h]quinoline, and 14HPyrimido[4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline Derivatives
Volume: 9 Issue: 5
Author(s): Abdullah Megbas Al-Ghamdi, Ashraf Hassan Fekry Abd El-Wahab, Hany Mostafa Mohamed, Ahmed Mohamed El-Agrody
Affiliation:
Keywords: HIV integrase, anti-proliferative effects, styrylquinoline derivatives, quinoline nucleus, benzaldehyde, HCT, IR spectrum, S.pyogens
Abstract: Several 4H-pyrano[3,2-h]quinoline 3,4,7-9, 7H-pyrimido[4',5':6,5]pyrano[3,2-h]quinoline 10a,b and 14Hpyrimido[ 4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline 11a-c derivatives were obtained by treatment of (E) 2-(4- chlorostyryl)-8-hydroxyquinoline 1, (E) 2-amino-4-(4-chlorophenyl)-9-(4-chlorostyryl)-4H-pyrano[3,2-h]quinoline-3- carbonitr-ile 3 or (E) 9-amino-7-(4-chlorophenyl)-2-(4-chlorostyryl)-8-imino-8,9-dihydro-7H-pyrimido-[4',5':6,5]pyrano [3,2-h]quinoline 10b with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR-DEPT, 13C NMR-APT and MS data. The antitumor activity of the synthesized compounds was investigated and compared with that of the standard drug vinblastine, a well-known anticancer drug, using MTT colorimetric assay. Among them, compounds 10b and 3 showed the most potent activity against the human breast tumor cells (MCF-7) and the human lung carcinoma cells (HCT), while compound 10b exhibited the most potent activity against the human hepatocellular carcinoma cells (HepG-2). The structure-activity relationships are discussed
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Abdullah Megbas Al-Ghamdi, Ashraf Hassan Fekry Abd El-Wahab, Hany Mostafa Mohamed, Ahmed Mohamed El-Agrody , Synthesis and Antitumor Activities of 4H-Pyrano[3,2-h]quinoline-3-carbonitrile, 7H-Pyrimido[4',5':6,5]pyrano[3,2-h]quinoline, and 14HPyrimido[4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline Derivatives , Letters in Drug Design & Discovery 2012; 9 (5) . https://dx.doi.org/10.2174/157018012800389331
DOI https://dx.doi.org/10.2174/157018012800389331 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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