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Review | Regular issue | Vol 102, No. 10, 2021, pp.1894-1937
Published online, 23rd March, 2021
DOI: 10.3987/REV-21-957
Synthesis and Structure−Activity Relationship Study of Intervenolin, an Antitumor and Anti-Helicobacter pylori Quinolone Natural Product

Takumi Watanabe*

*Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki Shinagawa-ku, Tokyo 141-0021, Japan

Abstract

This review article overviews the chemistry and biology of intervenolin, a quinolone natural product bearing unusual substituents. Intervenolin was isolated as a modulator of tumor–stroma interactions, communication between tumor cells and surrounding normal cells to regulate tumor-associated events including proliferation. The synthesis of intervenolin by the author employs thiocyanate–isothiocyanate rearrangement and Suzuki–Miyaura cross coupling as key reactions, which was utilized in structure–activity relationship studies. The SAR studies generated analogs that are effective in vivo. Moreover, several intervenolin and analogs also showed anti-Helicobacter pylori activity. Mechanistic aspects of these biological activities, and synthetic study on structurally related natural products by Spring and co-workers are also discussed.