Dapson in heterocyclic chemistry, part VIII: synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biologically active 1,3-dihydropyridine, chromene and chromenopyridine moieties

被引:50
作者
Al-Said, Mansour S. [1 ]
Ghorab, Mostafa M. [1 ]
Nissan, Yassin M. [2 ]
机构
[1] King Saud Univ, MAPPRC, Coll Pharm, Riyadh 11451, Saudi Arabia
[2] Cairo Univ, Dept Pharmaceut Chem, Fac Pharm, Cairo, Egypt
关键词
Sulfone; Pyridines; Chromenes; Pyridnochromenes; Anticancer activity; FARNESYL TRANSFERASE INHIBITORS; BLEOMYCIN-HAMSTER MODEL; INDUCED LUNG FIBROSIS; ANTITUMOR ACTIVITIES; SULFONE BISCOMPOUNDS; PULMONARY-FIBROSIS; PIRFENIDONE; CYTOTOXICITY; AGENTS; DERIVATIVES;
D O I
10.1186/1752-153X-6-64
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several new sulfonebiscompounds having a biologically active 1,2-dihydropyridine-2-one 3-19, acrylamide 20, chromene 21, 22 and chromenopyridine 23, 24 moieties were synthesized and evaluated as potential anticancer agents. The structures of the products were confirmed via elemental analyses and spectral data. The screening tests showed that many of the biscompounds obtained exhibited good anticancer activity against human breast cell line (MCF7) comparable to doxorubicin which was used as reference drug. Compounds 11, 17 and 24 showed IC50 values 35.40 mu M, 29.86 mu M and 30.99 mu M, respectively. In order to elucidate the mechanism of action of the synthesized compounds as anticancer agents, docking on the active site of farnesyltransferase and arginine methyltransferase was also performed and good results were obtained.
引用
收藏
页数:14
相关论文
共 51 条
[1]  
Adjei AA, 2001, CANC CHEMOTHER BIOL, V3, P161
[2]   Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives [J].
Al-Said, Mansour S. ;
Bashandy, Mahmoud S. ;
Al-Qasoumi, Saleh I. ;
Ghorab, Mostafa M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) :137-141
[3]   Cytochrome P450 1 enzyme inhibition and anticancer potential of chromene amides from Amyris plumieri [J].
Badal, S. ;
Williams, S. A. ;
Huang, G. ;
Francis, S. ;
Vendantam, P. ;
Dunbar, O. ;
Jacobs, H. ;
Tzeng, T. J. ;
Gangemi, J. ;
Delgoda, R. .
FITOTERAPIA, 2011, 82 (02) :230-236
[4]   Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1 [J].
Bissinger, Elisabeth-Maria ;
Heinke, Ralf ;
Spannhoff, Astrid ;
Eberlin, Adrien ;
Metzger, Eric ;
Cura, Vincent ;
Hassenboehler, Pierre ;
Cavarelli, Jean ;
Schuele, Roland ;
Bedford, Mark T. ;
Sippl, Wolfgang ;
Jung, Manfred .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (12) :3717-3731
[5]   Amiodarone-induced disruption of hamster lung and liver mitochondrial function: lack of association with thiobarbituric acid-reactive substance production [J].
Card, JW ;
Lalonde, BR ;
Rafeiro, E ;
Tam, AS ;
Racz, WJ ;
Brien, JF ;
Bray, TM ;
Massey, TE .
TOXICOLOGY LETTERS, 1998, 98 (1-2) :41-50
[6]   Differential effects of pirfenidone on acute pulmonary injury and ensuing fibrosis in the hamster model of amiodarone-induced pulmonary toxicity [J].
Card, JW ;
Racz, WJ ;
Brien, JF ;
Margolin, SB ;
Massey, TE .
TOXICOLOGICAL SCIENCES, 2003, 75 (01) :169-180
[7]   Protein arginine-methyltransferase-dependent oncogenesis [J].
Cheung, Ngai ;
Chan, Li Chong ;
Thompson, Alex ;
Cleary, Michael L. ;
So, Chi Wai Eric .
NATURE CELL BIOLOGY, 2007, 9 (10) :1208-1215
[8]   Synthesis and antitumour activity of 4-hydroxy-2-pyridone derivatives [J].
Cocco, MT ;
Congiu, C ;
Onnis, V .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (05) :545-552
[9]   Ras biochemistry and farnesyl transferase inhibitors: a literature survey [J].
Crul, M ;
de Klerk, GJ ;
Beijnen, JH ;
Schellens, JHM .
ANTI-CANCER DRUGS, 2001, 12 (03) :163-184
[10]   Synthesis of chlorovinyl sulfones as structural analogs of chalcones and their antiplasmodial activities [J].
Dominguez, Jose N. ;
Leon, Caritza ;
Rodrigues, Juan ;
Gamboa de Dominguez, Neira ;
Gut, Jiri ;
Rosenthal, Philip J. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (04) :1457-1462