SYNTHESIS OF NOVEL SYMMETRICAL PYRROLE, PYRAZOLE AND PYRIDINE DERIVATIVES STARTING FROM 1,8-DIAMINONAPHTHALIN

There was 9.6 million death in 2018 attributed to cancer that encouraged researchers to design novel antitumor agents which combat that fatal disease. In an attempt to establish new candidates with improved anticancer activity, N3,N3'-(naphthalene-1,8-diyl)bis(1H-pyrazole3,5diamine)3,1,1'-(naphthalene-1,8-diyl)bis(5-(4-chlorophenyl) -2-oxo-2,3-dihydro-1Hpyrrole-3carbonitrile) 4 and 1,1'-(naphthalene-1,8-diyl)bis(6-amino-4-(2,4-dimethoxyphenyl)2-oxo-1,2dihydropyridine-3,5 dicarbonitrile) 6 compounds were synthesized from the active binucleophile, 1,8-diaminonaphthaline. Firstly, N,N'-(naphthalene-1,8-diyl)bis(2cyanoacetamide) 2 was synthesized from 1,8-diaminonaphthaline through two methods, either converting 1,8diaminonaphthaline to N,N'-(naphthalene-1,8-diyl)bis(2chloroacetamide) 1 via reaction with chloroacetyl chloride followed by stirring with potassium cyanide in dry benzene, or by direct heating under reflux with ethyl cyanoacetate. Secondly, symmetrical polynuclear novel compounds 3, 4 and 6 were prepared from compound 2 via reaction with hydrazine hydrate, 4chlorophenacyl bromide and 2-(2,4-dimethoxybenzylidene) malononitrile 5, respectively. Structures of all synthesized compounds were confirmed via spectral data and elemental analyses. All synthesized compounds were sent for screening in National Cancer Institute, Bethesda, Maryland, United States of America and growth inhibition activity was under investigation