Thesis (Ph.D.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The starting N,N-bis(cyanoacetyl)hydrazine 3 was prepared by the reaction of cyanoacetic acid hydrazide 1 and 3-(3 ,5-dimethyl-1H-pyrazol-1-yl)-3- oxopropanenitrile 2. Condensation of compound 3 with each of aromatic aldehydes 4a-k, o-hydroxybenzaldehydes 8a,b and azosalicylaldehydes 12a-e under grind stone method afforded the respective arylmethylene derivatives Sak, his-coumarin derivatives lla,b and 15a-e, respectively. Coupling of 3 with aryldiazonium chlorides gave arylhydrazono derivatives 17a-e. Also , antimicrobial activity for some new products, enzyme inhibition and agarose gel electrophoresis were investigated. Next, malononitrile considered as the starting material to prepare 5-amino-3- (cyanomethyl)-1-phenyl-lH-pyrazole-4-carbonitrile 20. Acid hydrolysis of compound 20 gave 3-amino-2-phenyl-2,7-dihydro-4H-pyrazolo[ 4,3-c ]pyridine- 4,6(5H)-dione 39. Condensation of each of 20 and 39 with various aromatic aldehydes afforded the corresponding arylmethylenes 23a-i and 40a-I, respectively. Coupling of 39 with aryldiazonium chlorides led to formation of arylhydrazono derivatives 53a-e.Moroever, acetylation of 39 yielded the Nacetyl derivative 43. The anticancer activity of some of the newly synthesized compounds was investigated. Also, molecular docking study was performed

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