Synthesis, Antileukemic Activity, and Stability Of 3-(Substituted-Triazeno)pyrazole-4-carboxylic Acid Esters and 3-(Substituted-Triazeno)pyrazole-4-carboxamides
1971; Elsevier BV; Volume: 60; Issue: 4 Linguagem: Inglês
10.1002/jps.2600600408
ISSN1520-6017
AutoresY. Fulmer Shealy, C. Allen O’Dell,
Tópico(s)Click Chemistry and Applications
ResumoRepresentative 3-triazeno derivatives of the ethyl an methyl esters of pyrazole-4-carboxylic acid and of pyrazole-4-carboxamide were synthesized from the corresponding 3-diazopyrazoles. It was shown that certain triazenopyrazoles in solution are decomposed by light, and transformations of 3-(3-methyl-1-triazeno)pyrazole-4-carboxamide and 3-[3,3-bis(2-chloroethyl)-1-triazeno]pyrazole-4-carboxamide in solution in the dark to 3-aminopyrazole-4-carboxamide in solution in the dark to 3-aminopyrazole-4-carboxamide and to a v-triazolinium salt, respectively, were observed. All of these transformations are analogous to reactions of triazenoimidazoles observed previously. Triazenopyrazoles having both the ester and the amide groups increased the average survival time in the standard mouse L-1210 leukemia assay. In some of these tests, increases in lifespan of 60-120% were observed.
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