<abstract xmlns="http://www.w3.org/1999/xhtml">As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine <bold>4</bold>, thienopyridine <bold>5</bold>, isoquinolines <bold>6–20</bold>, acrylamide <bold>21</bold>, thiazolidine <bold>22</bold>, thiazoles <bold>23–29</bold> and thiophenes <bold>33–35</bold> bearing a biologically active quinoline nucleus were synthesized. The structure of newly synthesized compounds was confirmed on the basis of elemental analyses and spectral data. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. 2,3-Dihydrothiazole-5-carboxamides <bold>27</bold>, <bold>25</bold>, 4,5,6,7-tetrahydrobenzo[<italic>b</italic>]thiophene-3-carboxamide (<bold>34</bold>), 1,2-dihydroisoquinoline-7-carbonitrile (<bold>7</bold>), 5,6,7,8-tetrahydro-4<italic>H</italic>-cyclohepta[<italic>b</italic>]thiophene-3-carboxamide (<bold>35</bold>), 1,2-dihydroisoquinoline-7-carbonitrile (<bold>6</bold>), <bold><italic>2</italic></bold>-cyano-3-(dimethylamino)-<italic>N</italic>-(quinolin-3-yl)acrylamide (<bold>21</bold>), 1,2-dihydroisoquinoline-7-carbonitriles (<bold>11</bold>) and (<bold>8</bold>) exhibited higher activity (<italic>IC</italic>50 values of 27–45 μmol L–1) compared to doxorubicin (<italic>IC</italic>50 47.9 μmol L–1). LQ quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (<bold>12</bold>), 2-thioxo-2,3-dihydrothiazole-5-carboxamide (<bold>28</bold>) and quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (<bold>15</bold>) show activity comparable to doxorubicin, while (quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (<bold>9</bold>), 2,3-dihydrothiazole-5-carboxamide (<bold>24</bold>), thieno [3,4-<italic>c</italic>] pyridine-4(5<italic>H</italic>)-one (<bold>5</bold>), cyclopenta[<italic>b</italic>]thiophene-3-carboxamide (<bold>33</bold>) and (quinolin-3-yl)-6-stryl-1,2-dihydroisoquinoline-7-carbonitrile (<bold>10</bold>) exhibited moderate activity, lower than doxorubicin.</abstract>

As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine 4, thienopyridine 5, isoquinolines 6–20, acrylamide 21, thiazolidine 22, thiazoles 23–29 and thiophenes 33–35 bearing a biologically active quinoline nucleus were synthesized. The structure of newly synthesized compounds was confirmed on the basis of elemental analyses and spectral data. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. 2,3-Dihydrothiazole-5-carboxamides 27, 25, 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (34), 1,2-dihydroisoquinoline-7-carbonitrile (7), 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide (35), 1,2-dihydroisoquinoline-7-carbonitrile (6), 2-cyano-3-(dimethylamino)-N-(quinolin-3-yl)acrylamide (21), 1,2-dihydroisoquinoline-7-carbonitriles (11) and (8) exhibited higher activity (IC50 values of 27–45 μmol L–1) compared to doxorubicin (IC50 47.9 μmol L–1). LQ quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (12), 2-thioxo-2,3-dihydrothiazole-5-carboxamide (28) and quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (15) show activity comparable to doxorubicin, while (quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (9), 2,3-dihydrothiazole-5-carboxamide (24), thieno [3,4-c] pyridine-4(5H)-one (5), cyclopenta[b]thiophene-3-carboxamide (33) and (quinolin-3-yl)-6-stryl-1,2-dihydroisoquinoline-7-carbonitrile (10) exhibited moderate activity, lower than doxorubicin.

Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents

Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt

Medicinal, Aromatic and Poisonous, Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia

Acta Pharmaceutica

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine 4, thienopyridine 5, isoquinolines 6–20, acrylamide 21,...

Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents

Pubblicato online: 28 mag 2016

Pagine: 155 - 171

Accettato: 05 nov 2015

DOI: https://doi.org/10.1515/acph-2016-0016

Parole chiave
quinolines, pyridine, thienopyridine, isoquinoline, acrylamide, thiazole, thiophene, anticancer activity

© 2016 Mostafa M. Ghorab et al., published by De Gruyter Open

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents

Pubblicato online: 28 mag 2016

Pagine: 155 - 171

Accettato: 05 nov 2015

DOI: https://doi.org/10.1515/acph-2016-0016

Parole chiavequinolines, pyridine, thienopyridine, isoquinoline, acrylamide, thiazole, thiophene, anticancer activity

© 2016 Mostafa M. Ghorab et al., published by De Gruyter Open

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Parole chiave
quinolines, pyridine, thienopyridine, isoquinoline, acrylamide, thiazole, thiophene, anticancer activity