Synthese und biochemische Eigenschaften von heterocyclischen Thioäthern des 2-Chlor-6-mercaptopurins / Synthesis and Biochemical Properties of Heterocyclic Thioethers of 2-Chloro-6-mercaptopurine

Abstract

The synthesis of the following thioethers of 2-chloro-6-mercaptopurine is described: 2-chloro-6-[4-phenyl-imidazole-2-thio] purine; 2-chloro-6-[4-guanidopropyl-imidazole-2-thio] purine; 2-chloro-6-[4-t.butyl-thiazole-2-thio] purine;2-chloro-6-[4-phenyl-thiazole-2-thio] purine; 2-chloro-6-[4-methylthiazole-2-thio] purine;2-chloro-6-[4-carbethoxymethyl-thiazole-2-thio] purine; 2-chloro-6-[4-carboxamido-5-amino-thiazole-2-thio] purine; 2-chloro-6-[5-phenyl-thiadiazole (1,3,4) -2-thio] purine; 2-chloro-6-[5-t.butyl-thiadiazole (1,3,4) -2-thio] purine; 2-chloro-6-[tetrazole-5-thio] purine. The thioether bond of these compounds is cleaved by nucleophilic agents especially by mercaptanes under mild conditions. The compounds are not metabolized by ascites cells and preferentially bound to the cell surface. They are inhibitors of DNA-, RNA-, and proteinsynthesis and of proliferation of Ascites cells in a different degree; the ascites carcinoma of mice was not influenced. A possible mechanism of action of their metabolic effects is discussed.

Structural elucidation of propargylated products of 3‐substituted‐1,2,4‐triazole‐5‐thiols by NMR techniques

“…All the triazole thiols were prepared by following the reported procedures (R = H, [13] Me, [14] t-Bu, [15] p-C 6 H 4 Cl, [16] and p-C 6 H 4 OMe [16] ). Propargyl bromide was obtained from Sigma Aldrich Chemicals Private Limited and was used as such.…”