3-N-Substituted aminomethyl derivatives of rifamycin SV. A convenient method of synthesis, cyclization of certain derivatives, and anticellular and antiviral activities of several derivatives.
J Med Chem, 1977/10;20(10):1272-6.
McCarthy JR, Moore JL, Wysong DV
PMID: 198544
Impact factor: 8.039
Abstract
A new synthesis of Mannich bases of rifamycin SV using the Borch2 procedure with rifaldehyde is described. This new synthesis offers two advantages over the previously published method. It provides a route to monoalkyl-aminomethylrifamycins (le-h) and to unsubstituted aminomethylrifamycins that were not accessible by the old procedure. The new method also offers a preparative route to Mannich bases 1a and 1b were needed in multigram quantities for biological testing. In addition, the cyclization of certain of the monoalkylaminomethylrifamycins to the novel N,15-didehydro-15-epi[methano(alkylimino)]rifamycin SV derivatives (2) is described. The anticellular and antiviral effects of representatives of both series of compounds against cultured mouse cells and murine oncornavirus are are discussed.
MeSH terms
Animals; Antineoplastic Agents; Antiviral Agents; Cell Division; Cell Transformation, Neoplastic; Cells, Cultured; Cyclization; In Vitro Techniques; Leukemia Virus, Murine; Methods; Mice; Rifamycins; Sarcoma Viruses, Murine
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