Chemistry of Seven-Membered Heterocycles, VI. Synthesis of Novel Bicyclic Heterocyclic Compounds as Potential Anticancer and Anti-HIV Agents

Abstract

A bo u E lfatooh G. H am m am 3, N agla A. A bd E l-hafeza, W anda H. M idurab, and M arian M ikołajczykb a N ational R esearch C enter, D ep artm en t o f O rganic Chem istry, D o k k i, G iza, Egypt b C entre o f M olecular and M acrom olecular Studies, Polish A ca d em y o f Sciences, 9 0 -3 6 3 L odz, S ienk iew icza 112, Poland Reprint requests to Prof. M. M ikolajczyk. Fax: + 4 8 (0 )4 2 6 8 4 -7 1 -2 6 . E-mail: m arm ikol@ bilbo.cbm m .lodz.pl Z. Naturforsch. 55b, 4 1 7 -4 2 4 (2000); received N o v em b er 2, 1999 B enzothiep in o-pyrid in es, B icyclic Sulfones, H eterocyclization s Several new pyridines, pyridones and pyrans fused to b en zo th iep in e or b e n zo h ep ten e ring were synthesized as potential anticancer and an ti-H IV agents. T he fused-ring pyridines 6. 7 and 17-19 were obtained via the reaction o f the seven -m em b ered ring k eto n es 1, 2 and 3 with an arylidene-m alononitrile and by treatm ent o f the y lid en em alon on itriles 14, 15 and 16 with arom atic aldehydes, respectively. The correspon ding pyridon es 11, 12 and 13 w ere pre pared from the k eton es 1, 2 and 3 and arylm eth ylen ecyan oacetam id e. The synthesis o f the fused-ring pyranes 8 and 9 involved the co n d en sation o f the k eto n es 4 and 5 with m alononitrile under basic conditions. The rearrangem ent o f 8 under acidic con d ition s gave the tetrahydropyridine 10. The pyran 20 was ob tain ed from 15 and b en zaldehyd e. The screening tests sh ow ed that m any o f the com poun ds ob tain ed exhibit g o o d anticancer activity com parable to 5-fluorodeoxyurid in e used as reference com p ou n d and m od erate an ti-H IV activity in co m parison with AZT.

Antiarrhythmic Activities of Some Newly Synthesized Tricyclic and Tetracyclic Thienopyridine Derivatives

“…As part of our program in this area, we have synthesized some pyridine and thiazolopyrimidine derivatives of biological interest as anticancer activity [1][2][3][4][5]. On the other hand, thienopyrimidine and thioxopyrimidine derivatives have promising biological [6,7] and inhibitor of VEGFR-2 kinase activity [8,9].…”

Synthesis and Characterization of New 1,2-Dihydropyridine-3-Carbonitrile Compounds with Study of Expected Biological Activity

“…The pyridine nucleus was an integral portion from anticancer and anti-inflammatory agents [13] else. On the anther hand, cyanopyridone and cyanopyridine derivatives have been shown for owns promising antimicrobial [14] and anticancer activities [15]. This investigation demonstrated synthesis of new 1,2-dihydropyridine-3carbonitrile compounds derived from 7hydroxy-4-methyl-2H-chromen-2-one with fully characterization, and aiming to further biochemical studies.…”

A new investigation for some steroidal derivatives as anti-Alzheimer agents

“…It has been mentioned in a number of literatures that some steroidal [6][7][8] and heterocyclic derivatives were found to posses analgesic, anticonvulsant, antiandrogenic agents, anti-inflammatory and antimicrobial activity [9][10][11][12][13]. Furthermore, pyrimidone and cyanoiminopyrimidine derivatives have shown as a promising antimicrobial agent [14,15] as well as anticancer activities [16][17][18][19][20]. In view of these reports and in continuation of our previous works in heterocyclic chemistry, we have herein screened some compounds containing pyrimidine and cyclohexenone ring fused with steroidal structure for their evaluation as anti-Alzheimer agents.…”