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  • Title: Synthesis and modeling studies with monocyclic analogues of mycophenolic acid.
    Author: Anderson WK, Boehm TL, Makara GM, Swann RT.
    Journal: J Med Chem; 1996 Jan 05; 39(1):46-55. PubMed ID: 8568826.
    Abstract:
    Two stepwise procedures, developed for the introduction of the (E)-4-methyl-4-hexenoic acid side chain of mycophenolic acid, were used in the synthesis of monocyclic mycophenolic acid analogues 2a-i. The derivatives with a methyl group or hydrogen at C-4 and lacking the lactone moiety were much less cytotoxic than mycophenolic acid. The monocyclic analogues with a C-4 chloro group did show some activity, albeit much less than mycophenolic acid. The observed differences in potency are rationalized by semiempirical calculations of intramolecular H-bonds.
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