J Med Chem. 1982 Jun;25(6):663-6.
Structure-activity correlations of cytochalasins. Novel
halogenated and related cytochalasin C and cytochalasin D
derivatives.
Patwardhan BH, Flashner M, Miller CA, Tanenbaum SW.
A series of halogenated and related analogues of cytochalasin C
and cytochalasin D has been synthesized, and the biological
activities of the analogues as inhibitors in a cell-free
contractility model system obtained from Ehrlich ascites tumor
cells were evaluated. The reaction sequence involved treatment
of cytochalasin D with phenyltrimethylammonium perbromide
to give 6,12-dibromo-cytochalasin D (2),
dehydrohalogenation of 2 to 12-bromo-cytochalasin C
(3), and the subsequent conversions of 3 to 12-azido- (4),
12-iodo- (5), and 12-cyano-cytochalasin C (6). The ID50
values for 5, 3, 4, 2, and 6 are 6.0, 7.4, 8.8, 45, and 77 X
10(-7) M, respectively, in comparison to ca. 2.8 X 10(-7) M for
the parental compounds. The potential cell and molecular
biological applications of these compounds are delineated.
PMID: 7097721
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