An unprecedented synthesis of polysubstituted indole-fused pyridazines (azacarbolines) from α-indolylhydrazones under oxidative conditions using a combination of iodylbenzene (PhIO) and trifluoroacetic acid (TFA) has been developed. This transformation is conducted without the need for transition metals, harsh conditions, or an inert atmosphere.
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http://dx.doi.org/10.1021/acs.joc.1c02217 | DOI Listing |
Molecules
February 2022
School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013, China.
Tubulin inhibitors can interfere with normal cell mitosis and inhibit cell proliferation through interfering with the normal structure and function of microtubules, forming spindle filaments. Indole, as a privileged pharmacological skeleton, has been widely used in anti-cancer inhibitors. A variety of alkaloids containing an indole core obtained from natural sources have been proven to inhibit tubulin polymerization, and an ever-increasing number of synthetic indole-based tubulin inhibitors have been reported.
View Article and Find Full Text PDFJ Org Chem
December 2021
Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, Italy.
An unprecedented synthesis of polysubstituted indole-fused pyridazines (azacarbolines) from α-indolylhydrazones under oxidative conditions using a combination of iodylbenzene (PhIO) and trifluoroacetic acid (TFA) has been developed. This transformation is conducted without the need for transition metals, harsh conditions, or an inert atmosphere.
View Article and Find Full Text PDFFuture Med Chem
July 2016
Pharmaceutical Sciences Department, College of Pharmacy, Rosalind Franklin University of Medicine & Science, 3333 Green Bay Road, North Chicago, IL 60064, USA.
Discovery of new indole-based tubulin polymerization inhibitors will continue to dominate the synthetic efforts of many medicinal chemists working in the field. The indole ring system is an essential part of several tubulin inhibitors identified in the recent years. The present review article will update the synthesis, anticancer and tubulin inhibition activities of several important new indole classes such as 2-phenylindoles (28, 29 & 30), oxindoles (35 & 38), indole-3-acrylamides (44), indolines (46), aroylindoles (49), carbozoles (75, 76 & 82), azacarbolines (87) and annulated indoles (100-105).
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