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. Author manuscript; available in PMC: 2017 Dec 6.
Published in final edited form as: J Org Chem. 2017 Oct 13;82(23):11961–11980. doi: 10.1021/acs.joc.7b02088

Figure 7.

Figure 7

Active analogs required a single heavy atom exchange into the vinblastine structure (C20′ NH2 for OH). In a plot of −log IC50 (nM, HCT116) versus substituent σp, the analogs additionally displayed a predictable modulation of activity by a substituent (X) electronic effect, impacting benzamide carbonyl H-bonding with tubulin, some representing single heavy atom additions. All analogs shown are more active than vinblastine.