1-beta-d-arabinofuranosyl cytosine derivatives and methods of preparing

Abstract

Abstract 2,2''-ANHYDRO-1-(3''-O-ACYL-B-D-ARABINOFURANOSYL) CYTOSINE SALT DERIVATIVES; (S) 2,2''-ANHYDRO-1-(3''-O-ACYLB-D-ARABINOFURANOSYL)-2-THIOCYOSINE SALT DERIVATIVES; 1-(B-D-ARABINOFURANOSYL)-5-AZAACYTOSINE DERIVATIVES AND 1-(2''-THIO-B-D-ARABINOFURANOSYL) CYTOSINE AND METHODS OF PREPARING SUCH COMPOUNDS AND CONVERTING THE AFOREMENTIONED 2,2''-ANHYDRO DERIVATES. THE 2, TO THE CORRESPONDING 1-BD-ARABINOFURANOXYL CYTOSINE DERIVATIVES. THE 2,2''-ANHYDRO-1-(3''-O-ACYL-B-DARABINOFURANOSYL) CYTOSINE AND (S) 2,2''-ANHYDRO-1-(3''-O-ACYL-B-D-ARABINOFURANOSYL)-2THIOCYTOSINE DERIVATIVES ARE PREPARED BY TREATING THE CORRESPONDING CYTOSINE RIBONUCLEOSIDES WITH A SUITABLE AACYLOXY ACID HALIDE. OTHER PHARMACEUTICALLY ACCEPTABLE SALTS CAN BE PREPARED BY ION EXCHANGE. TREATMENT OF THESE DERIVATIVES WITH AN AQUEOUS ALKALINE SOLUTION AFFORDS THE CORRESPONDING 1-(B-D-ARABINOFURANOSYL) CYTOSINE NUCLEOSIDES. THE 2,2''-ANHYDRO-1-(3''-O-ACYL-B-D-ARABINOFURANOSYL) CYTOSINE; (S) 2,2''-ANHYDRO-1-(3''-O-ACYL-B-D-ARABINOFURANOSYL)-2-THIOCYTOSINE AND 1-(B-D-ARABINOFURANOSYL)5-AZACYTOSINE DERIVATIVES AND 1-(2''-THIO-B-D-ARABINOFURANOSYL) CYTOSINE EXHIBIT ANTIVIRAL AND CYTOTOXIC ACTIVITY, AND THE 2,2''-ANHYDRO DERIVATIVES ARE FURTHER USEFUL AS INTERMEDIATES FOR THE PREPARATION OF 1-(B-D-ARABINOFURANOXYL) CYTOSINES WHICH ALSO HAVE UTILITY AS ANTIVIRAL AN CYTOTOXIC AGENTS.

Inventors

• 👤 J Moffatt
• 👤 A Russell

Bibliographic Details