New Bis(dihydropyridine-3,5-dicarbonitrile) Derivatives: Green Synthesis and Cytotoxic Activity Evaluation

被引:51
作者
Abdelmoniem, Amr M. [1 ]
Salaheldin, Taher A. [2 ]
Abdelhamid, Ismail A. [1 ]
Elwahy, Ahmed H. M. [1 ]
机构
[1] Cairo Univ, Dept Chem, Fac Sci, Giza, Egypt
[2] Agr Res Ctr, Nanotechnol & Adv Mat Cent Lab, Cairo 12631, Egypt
关键词
SUBSTITUTED MACROCYCLIC LIGANDS; HETEROCYCLIC SYNTHESIS; ANTITUMOR AGENTS; PRECURSORS; INHIBITORS; SUBUNITS; PYRIDINE; ANALOGS;
D O I
10.1002/jhet.2867
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of bis(dihydropyridine-3,5-dicarbonitrile) by a three-component reaction of one equivalent of bis-cyanoacetamides with two equivalents of both arylaldehydes and malononitrile in ethanol-containing piperidine is reported. Bis-cyanopyridones could also be obtained by the condensation of bis-cyanoacetamides with substituted arylidenemalononitriles in the presence of piperidine, chitosan, or montmorillonite as basic catalysts. The cytotoxicity of the synthesized products against the heterogeneous human epithelial colorectal adenocarcinoma cell line (Caco-2) was assessed by WST-1 assay with concentration dependent cellular growth inhibitory effect especially for compounds 5l, 5h, and 5d. The dose response curves indicate that IC50 were 87 +/- 3.11g/mL, 104 +/- 4.78g/mL, and 108 +/- 5.12g/mL, respectively.
引用
收藏
页码:2670 / 2677
页数:8
相关论文
共 48 条
[1]  
Abdelhamid I. A., 2010, SYNTHESIS, V1107
[2]  
Abdelhamid IA., 2008, SYNLETT, V10, P625
[3]   Synthesis and characterization of poly(2,6-dimethyl-4-phenyl-1,4-dihydropyridinyl)arenes as novel multi-armed molecules [J].
Abdelhamid, Ismail A. ;
Darweesh, Ahmed F. ;
Elwahy, Ahmed H. M. .
TETRAHEDRON LETTERS, 2015, 56 (51) :7085-7088
[4]   DBU-Catalyzed, facile and efficient method for synthesis of spirocyclic 2-oxindole derivatives with incorporated 6-amino-4H-pyridazines and fused derivatives via [3+3] atom combination [J].
Abdelhamid, Ismail A. ;
Mohamed, Mona H. ;
Abdelmoniem, Amr M. ;
Ghozlan, Said A. S. .
TETRAHEDRON, 2009, 65 (48) :10069-10073
[5]   Multicomponent Synthesis of Novel bis(2-amino-tetrahydro-4H-chromene-3-carbonitrile) Derivatives Linked to Arene or Heteroarene Cores [J].
Abdella, Amna M. ;
Elwahy, Ahmed H. M. ;
Abdelhamid, Ismail A. .
CURRENT ORGANIC SYNTHESIS, 2016, 13 (04) :601-610
[6]   Synthesis and biological evaluation of novel 2,4′-bis substituted diphenylamines as anticancer agents and potential epidermal growth factor receptor tyrosine kinase inhibitors [J].
Abou-Seri, Sahar Mahmoud .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :4113-4121
[7]  
Al-mousawi S. M., 2011, CURRENT, V3503
[8]   Anti-inflammatory profile of some synthesized heterocyclic pyridone and pyridine derivatives fused with steroidal structure [J].
Amr, Abdel-Galil E. ;
Abdulla, Mohamed M. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) :4341-4352
[9]   Efficient synthesis of new butenolides by subsequent reactions: application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones [J].
Cheikh, Nawel ;
Bar, Nathalie ;
Choukchou-Braham, Nourredine ;
Mostefa-Kara, Bachir ;
Lohier, Jean-Francois ;
Sopkova, Jana ;
Villemin, Didier .
TETRAHEDRON, 2011, 67 (08) :1540-1551
[10]   Antitumor agents .178. Synthesis and biological evaluation of substituted 2-aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization [J].
Chen, K ;
Kuo, SC ;
Hsieh, MC ;
Mauger, A ;
Lin, CM ;
Hamel, E ;
Lee, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (19) :3049-3056