Arabinofuranosyl cytosines and methods of making

Details Arabinofuranosyl cytosines and methods of making Arabinofuranosyl cytosines and methods of making

1972-03-03

1976-12-21

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, C07H 1908

Patent

active

039988074

ABSTRACT:
3'-O-Acyl- and 3-'-O-acyl-5-'-O-acyl- derivatives of 1-(.beta.-D-arabinofuranosyl)-cytosines and methods of preparing these compounds and also O.sup.2,2'-anhydro-1-(3'-O-acyl-5'-O-acyl-.beta.-D-arabinofuranosyl)-cytos ine salts. The O.sup.2,2'-anhydro-1-(3'-O-acyl-5'-O-acyl-.beta.-D-arabinofuranosyl)-cytos ine nucleoside salts are prepared by direct acid catalyzed acylation of the salts of the corresponding O.sup.2,2'-anhydro-1-(.beta.-D-arabinofuranosyl)-cytosines or 3'-O-acyl- derivatives, under carefully controlled conditions. The 3'-O-acyl- and 3'-O-acyl-5'-O-acyl-1-(.beta.-D-arabinofuranosyl)-cytosines are prepared from the corresponding O.sup.2,2'-anhydro nucleosides via selective cleavage of the O.sup.2,2'-anhydro bridge under carefully controlled conditions. The compounds exhibit anti-viral, cytotoxic and anti-neoplastic activity, and thus are useful for the treatment of mammals where such agents are indicated.

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Montgomery et al., J. Medicinal Chem., vol. 15, No, 1, 1971, pp. 116-118.

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