Synthesis of Conformationally Liberated Yohimbine Analogues and Evaluation of Cytotoxic Activity.

Authors :: Yang H
Poznik M
Tang S
Xue P
Du L
Liu C
Chen X
Chruma JJ
Source :: ACS omega [ACS Omega] 2021 Jul 13; Vol. 6 (29), pp. 19291-19303. Date of Electronic Publication: 2021 Jul 13 (Print Publication: 2021).
Publication Year :: 2021
Abstract: A modular synthetic approach to strategically unique structural analogues of the alkaloid yohimbine is reported. The overall synthetic strategy couples the transition-metal-catalyzed decarboxylative allylation of 2,2-diphenylglycinate imino esters with a scandium triflate-mediated highly endo-selective intramolecular Diels-Alder (IMDA) cycloaddition to generate a small collection of de-rigidified yohimbine analogues lacking the ethylene linkage between the indole and decahydroisoquinoline units. One compound generated in this study contains an unprecedented pentacyclic urea core and appears to demonstrate increased cytotoxicity against the gastric cancer cell line SGC-7901 in comparison to a pancreatic cancer cell line (PATU-8988) and a normal human gastric mucosal cell line (GES-1).<br />Competing Interests: The authors declare no competing financial interest.<br /> (© 2021 The Authors. Published by American Chemical Society.)

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