The short way to chiral compounds with hexahydrofluoreno[9,1-bc]furan framework: synthesis and cytotoxic activity

Svetlana Yu Kurbakova; Irina V Il'ina; Oksana S Mikhalchenko; Mikhail A Pokrovsky; Dina V Korchagina; Konstantin P Volcho; Andrey G Pokrovsky; Nariman F Salakhutdinov

doi:10.1016/j.bmc.2015.02.013

The short way to chiral compounds with hexahydrofluoreno[9,1-bc]furan framework: synthesis and cytotoxic activity

Bioorg Med Chem. 2015 Apr 1;23(7):1472-80. doi: 10.1016/j.bmc.2015.02.013. Epub 2015 Feb 16.

Authors

Svetlana Yu Kurbakova¹, Irina V Il'ina², Oksana S Mikhalchenko¹, Mikhail A Pokrovsky³, Dina V Korchagina¹, Konstantin P Volcho⁴, Andrey G Pokrovsky³, Nariman F Salakhutdinov²

Affiliations

¹ N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation.
² N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
³ Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.
⁴ N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation. Electronic address: volcho@nioch.nsc.ru.

PMID: 25737086
DOI: 10.1016/j.bmc.2015.02.013

Abstract

A simple and efficient method for synthesizing chiral heterocyclic compounds with the hexahydrofluoreno[9,1-bc]furan framework via interaction between trans-4-hydroxymethyl-2-carene and aromatic aldehydes containing methoxy and hydroxyl moieties in the presence of montmorillonite clay was found. One of the synthesized compounds exhibited a high cytotoxic activity against lymphoblastoid cell line MT-4 (CTD50 0.9μM), which was higher than that of the comparative drug Doxorubicin. Death of cancer cells in this case substantially occurs via induction of apoptosis.

Keywords: Antitumor activity; Apoptosis; Carene; Clay; Cytotoxicity; Heterocycle; Terpene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / toxicity*
Apoptosis / drug effects
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Drug Screening Assays, Antitumor / methods
Fluorenes / chemical synthesis
Fluorenes / toxicity
Furans / chemical synthesis*
Furans / toxicity*
Humans
Structure-Activity Relationship

Substances

Antineoplastic Agents
Fluorenes
Furans
furan