Anti-breast cancer activity of some novel quinoline derivatives
To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2–24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR an...
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doaj-bab871df33214b10a24b3a111fa140ab2021-09-06T19:39:38ZengSciendoActa Pharmaceutica1846-95582015-09-0165327128310.1515/acph-2015-0030acph-2015-0030Anti-breast cancer activity of some novel quinoline derivativesGhorab Mostafa M.0Alsaid Mansour S.1Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaTo discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2–24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectroscopies. In addition, the structure of compound 1 was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(quinolin-3-yl) acrylamide (15), 3-oxo-N-(quinolin-3-yl)-3H-benzol[f] chromene-2-carboxamide (27), 2-cyano-3-(4-fluorophenyl-N-(quinolin-3-yl) acrylamide (7), 2-cyano-5-(4-(dimethyl-amino) phenyl)-N-(quinolin-3-yl) penta-2,4-dienamide (19) exhibited higher activity compared to doxorubicin (with IC50 value of 47.9 μmol L−1) as a reference drug, with IC50 values of 29.8, 39.0, 40.0, 40.4 μmol L−1, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl 17, 2-chlorophenyl 10, benzo[d][1,3]dioxol 12, 2-methoxynaphthalen 22, 2,4-dichlorophenyl 18 and quinoline carrying a chromene-3-carboxamide moiety 25 were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl 2, p-tolyl 3, 2,4-dienamide 8, 3-nitrophenyl 13, 4-nitrophenyl 14, 3,4-dimethoxyphenyl 16 and chromene 26 exhibited a moderate activity. In addition, quinoline with acetamide 1, 4-hydroxyphenyl 4, 4-dimethylaminophenyl 9, 4-chlorophenyl 11, 3-bromophenyl 20, 4-bromophenyl 21 and 3-thienyl moiety 24 showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl 5, 4-methoxyphenyl 6, 4-metho xynaphthalene 23 and chromene-2-carboxamide 28 showed no activity.https://doi.org/10.1515/acph-2015-0030quinolineacrylamideschromenesbenzochromenesanti-breast cancer activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ghorab Mostafa M. Alsaid Mansour S. |
spellingShingle |
Ghorab Mostafa M. Alsaid Mansour S. Anti-breast cancer activity of some novel quinoline derivatives Acta Pharmaceutica quinolineacrylamides chromenes benzochromenes anti-breast cancer activity |
author_facet |
Ghorab Mostafa M. Alsaid Mansour S. |
author_sort |
Ghorab Mostafa M. |
title |
Anti-breast cancer activity of some novel quinoline derivatives |
title_short |
Anti-breast cancer activity of some novel quinoline derivatives |
title_full |
Anti-breast cancer activity of some novel quinoline derivatives |
title_fullStr |
Anti-breast cancer activity of some novel quinoline derivatives |
title_full_unstemmed |
Anti-breast cancer activity of some novel quinoline derivatives |
title_sort |
anti-breast cancer activity of some novel quinoline derivatives |
publisher |
Sciendo |
series |
Acta Pharmaceutica |
issn |
1846-9558 |
publishDate |
2015-09-01 |
description |
To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2–24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectroscopies. In addition, the structure of compound 1 was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(quinolin-3-yl) acrylamide (15), 3-oxo-N-(quinolin-3-yl)-3H-benzol[f] chromene-2-carboxamide (27), 2-cyano-3-(4-fluorophenyl-N-(quinolin-3-yl) acrylamide (7), 2-cyano-5-(4-(dimethyl-amino) phenyl)-N-(quinolin-3-yl) penta-2,4-dienamide (19) exhibited higher activity compared to doxorubicin (with IC50 value of 47.9 μmol L−1) as a reference drug, with IC50 values of 29.8, 39.0, 40.0, 40.4 μmol L−1, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl 17, 2-chlorophenyl 10, benzo[d][1,3]dioxol 12, 2-methoxynaphthalen 22, 2,4-dichlorophenyl 18 and quinoline carrying a chromene-3-carboxamide moiety 25 were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl 2, p-tolyl 3, 2,4-dienamide 8, 3-nitrophenyl 13, 4-nitrophenyl 14, 3,4-dimethoxyphenyl 16 and chromene 26 exhibited a moderate activity. In addition, quinoline with acetamide 1, 4-hydroxyphenyl 4, 4-dimethylaminophenyl 9, 4-chlorophenyl 11, 3-bromophenyl 20, 4-bromophenyl 21 and 3-thienyl moiety 24 showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl 5, 4-methoxyphenyl 6, 4-metho xynaphthalene 23 and chromene-2-carboxamide 28 showed no activity. |
topic |
quinolineacrylamides chromenes benzochromenes anti-breast cancer activity |
url |
https://doi.org/10.1515/acph-2015-0030 |
work_keys_str_mv |
AT ghorabmostafam antibreastcanceractivityofsomenovelquinolinederivatives AT alsaidmansours antibreastcanceractivityofsomenovelquinolinederivatives |
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