Acta Pharm. 65 (2015) 155-171
Original research paper
Novel quinolines carrying pyridine, thienopyridine,
isoquinoline, thiazolidine, thiazole and thiophene moieties as potential
anticancer agents
MOSTAFA M. GHORAB,
MANSOUR S. ALSAID, MOHAMMED S. AL-DOSARI, FATMA A. RAGAB, ABDULLAH A.
AL-MISHARI and ABDULAZIZ N. ALMOQBIL
1 Department of Pharmacognosy, College
of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of
Saudi Arabia
2 Pharmaceutical Chemistry Department, Faculty of
Pharmacy, Cairo University, Cairo 11562, Egypt
3 Medicinal, Aromatic and
Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud
University; P.O. Box 2457, Riyadh 11451, Saudi Arabia
Accepted November 5, 2015
As a part of ongoing studies in developing new anticancer agents, a class of structurally 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 μM), compared to doxorubicin (IC50 47.9 μmol L–1). (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 comparable activity 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.
Keywords: quinolines,
pyridine, thienopyridine, isoquinoline, acrylamide, thiazole, thiophene,
anticancer activity