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Short Paper | Regular issue | Vol 106, No. 4, 2023, pp.725-733
Published online, 28th February, 2023
DOI: 10.3987/COM-23-14816
■ One-Pot Synthesis of Carbazoles by a Domino Reaction Using Microwave Heating and Antiproliferative Activities of Constituents from Murraya Plants Against Cancer Stem Cells

Kouta Ugawa, Momona Nakao, Chikako Sawada, Takahiro Matsumoto, Takahiro Kitagawa, Yutaro Ohki, Kousuke Araki, and Seikou Nakamura*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

Carbazoles could be easily and rapidly synthesized in a one-pot synthesis using 4-methyl-1-cyclohexanone and p-anisidine in a continuous microwave-heated reaction (1 h, 140 °C). Eustifoline-B, a trace constituent of the roots of Murraya euchrestifolia, was synthesized using the carbazole derivative glycozoline obtained by this method. Next, nine carbazoles isolated from the leaves of M. koenigii and three synthetic carbazoles were evaluated for their antiproliferative activities against human astrocytoma U-251 MG cells [that is, non-cancer stem cells (non-CSCs)] and cancer stem cells (CSCs) isolated by sphere formation. Carbazoles with geranyl or prenyl moieties showed antiproliferative activity against U-251 MG CSCs. In particular, the synthetic compound eustifoline-B showed significant antiproliferative activity against U-251 MG CSCs (IC50 = 2.9 μM). Interestingly, eustifoline-B showed an approximately 10-fold higher antiproliferative activity against U-251 MG CSCs than against U-251 MG non-CSCs (IC50 = 29.4 μM).