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Diamines, dicarboxamides, and disulfonamides that have terminal benzene, methyl- or chloro-substituted benzene rings were synthesized and evaluated for the activity of [3H]vinblastine accumulation in multidrug-resistant P388/ADR cells. The efficacy of these compounds was generally in the order of dicarboxamides &lt; diamines &lt; disulfonamides. N-Methylated diamine and disulfonamide compounds having terminal methyl- or chloro-substituted benzene rings in their structure also showed rather potent efficacy. From these findings, we synthesized a novel disulfonamide compound, 1,2,3,4,5,6-hexahydro-2,5-bis(p-toluenesulfonyl)benzo[2,5]diazocine++ + (22). Compound 22 suppressed the efflux of vinblastine from P388/ADR cells and increased its intracellular accumulation, while it barely increased the vinblastine accumulation in sensitive cells (P388/S). Compound 22 significantly potentiated the growth-inhibitory effects of vinblastine, vincristine, colchicine and Adriamycin against P388/ADR cells in vitro.

Structure-Activity Relationships of Diamines, Dicarboxamides, and Disulfonamides on Vinblastine Accumulation in P388/ADR Cells.