Amidrazones as precursors of biologically active compounds--synthesis of diaminopyrazoles for evaluation of anticancer activity.
The regioselectivity of coupling phenyl isocyanate to 3-(2-acylhydrazino)-3-aminopropenenitriles and ethyl 3-(2-acylhydrazino)-3-aminopropenoates as simple access to aminopyrazole derivatives, endowed with potential antitumoral activity, is reported. 3-(2-Acylhydrazino)-3-aminopropenenitriles react with phenyl isocyanate to afford 3-amino-3-(2-acylhydrazino)-2-phenylaminocarbonyl-2-propenenitriles. These key intermediates were cyclized into 3,5-diaminopyrazole-4-carboxamide derivatives. Preliminary results of poor antiproliferative activities of these compounds are also reported.
Cocco
Maria Teresa
MT
Dipartimento di Tossicologia, Università degli Studi di Cagliari, Cagliari, Italy. tcocco@unica.it
Congiu
Cenzo
C
Lilliu
Valentina
V
Onnis
Valentina
V
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D006835:Hydrazones / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D003959:Diamines; D006835:Hydrazones; D017953:Isocyanates; D011720:Pyrazoles; C025319:phenyl isocyanate