Preparation and Biological Activity of Retinoic Acid Analogs Containing an Aromatic Ring

Akimori Wada; Yukari Mizuguchi; Masaki Shinmen; Masayoshi Ito; Kimie Nakagawa; Toshio Okano

doi:10.2174/157018006775789711

ISSN: 1570-1808
E-ISSN: 1875-628X

Preparation and Biological Activity of Retinoic Acid Analogs Containing an Aromatic Ring
Authors: Akimori Wada¹, Yukari Mizuguchi², Masaki Shinmen³, Masayoshi Ito⁴, Kimie Nakagawa⁵ and Toshio Okano⁶
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¹ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. ² Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. ³ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. ⁴ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. ⁵ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. ⁶ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan.
Source: Letters in Drug Design & Discovery, Volume 3, Issue 2, Mar 2006, p. 118 - 122
DOI: https://doi.org/10.2174/157018006775789711
- Available online: 01 Mar 2006

Abstract

Retinoic acid analogs, which contain an aromatic ring fixed between the 5 and 8 positions of retinoic acid, were synthesized by a palladium catalyzed coupling reaction between an enol triflate and a tributylstannylolefin and their biological activities were subsequently evaluated. None of the analogs exhibited antiproliferative, differentiation-inducing, or apoptosis-inducing activities in HL 60 cells. However, the 9Z-derivatives of indene and benzofuran showed a strong binding affinity for the RXR receptor compared to that of 9CRA.

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2006-03-01

2025-09-22

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Article Type: Research Article

Keyword(s): coupling reaction; enol triflate; RAR; retinoic acid analogs; RXR

Preparation and Biological Activity of Retinoic Acid Analogs Containing an Aromatic Ring

Abstract

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