The apoptosis-inducing ability of α-ethano bridged crinane alkaloids was investigated using natural and semi-synthetic derivatives uncovering novel structural requirements of this cytotoxic pharmacophore. An α-ethano bridge is required; an α- or β-methoxy or hydroxyl H-bond acceptor are all tolerated at C-3; a small substituent (H, or OH) alone is tolerated at C-11; and a C-1 to C-2 double bond is shown to modulate, but is not a requirement for, apoptosis-inducing activity.
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McNulty, J., Nair, J. J., Bastida, J., Pandey, S., & Griffin, C. (2009). Structure activity studies on the crinane alkaloid apoptosis-inducing pharmacophore. Natural Product Communications, 4(4), 483–488. https://doi.org/10.1177/1934578x0900400408