Tetra-N-butylammonium fluoride as a novel reagent for the preparation of a cyclonucleosides: the synthesis of 9- [[2-hydroxyethoxy] methyl] adenine, bitamycin

The synthesis of the title compound, bitamycin [1], by means of Bu 4NF is described. This new antiviral drug was found to be one of the most powerful and least toxic substances for antiviral therapy in man. The physical and chemical behavior as well as the antiviral activities and clinical properties of this compound were found to be significantly different from that reported by Schaeffer, et al. Although the latter was claimed to have structure 1, we found it to possess structure 2. Bu 4NF was proved to be an effective reagent for the exclusive preparation of N [9]-alkylated products of purines. Condensation reactions and deprotection of the acyl-protecting groups to yield acyclo-nucleoside analogues were performed in a one step reaction

Treatment of one case of malignant melanoma with N-retinoylarabinocytidine

The synthesis of N-retinoylara-C is described. It is a new anticancer agent which was found to cause disease-free survival of more than three years duration in a patient with malignant melanoma of the nose, incompletely excised with metastasis to submandibular lymph nodes. He received a total of 1200 mg within 6 months, 50 mg weekly, IM. He developed minimal hypervitaminosis A syndrome [somnolence, conjunctivitis and splenomegaly] which recovered a few months after termination of therapy