Some short-chain N6-substituted adenosine analogs with antitumor properties

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Abstract
The compounds N6-allyl-, N6-isopropyl-, N6-propargyl- and N6-(2-methylally)adenosine were prepared by reacting 6-chloropurine riboside with an excess of the corresponding amines in ethanol, in the presence of 2 acid acceptors resulting in virtually quantitative yields. The compounds showed biological activity in a number of in vitro and in vivo [mouse, rat and human] tumor cell systems. Very good increases in life spans of mice bearing spontaneous mammary carcinoma were obtained by treatment with the N6-allyl, N6-isopropyl and N6-propargyl analogs, respectively. In rats, the N6-allyl analog slowed the rate of transplantable mammary tumor [Tw-98 cells]-growth by 1/4. The short-chain adenosine analog are more active in the treatment of animal carcinomas than in the [mouse L-1210] leukemia or [mouse S-180] sarcoma tumor cell systems.