Synthesis and an evaluation of the bioactivity of the C-glycoside of pseudopterosin A methyl ether

The Journal of Organic Chemistry
Wei ZhongR Daniel Little

Abstract

The Suzuki-Miyaura cross-coupling protocol was applied to the synthesis of 1a, the C-glycoside analogue of PsA methyl ether. This marks the first construction of a C-glycoside for this class of marine natural products, thereby offering an opportunity to compare its bioactivity to the natural substances. Its activity profile resembled that of PsA (1) and PsA O-methyl ether (1b) when assayed for its anti-inflammatory activity and its ability to inhibit phagocytosis. We conclude that the intact structure is present when a pseudopterosin expresses its anti-inflammatory and phagocytosis inhibitory properties and that they are, therefore, not likely to be prodrugs. Results show that 1a is an effective binding agent toward the A2A and A3 adenosine receptors, displaying IC50 values of 20 and 10 microM, respectively.

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Citations

Sep 10, 2009·The Journal of Organic Chemistry·Ileana I RodríguezHong Zhao
Nov 19, 2015·Carbohydrate Research·Karin ThorsheimUlf Ellervik
Nov 6, 2015·Mediators of Inflammation·Yisett GonzálezPatricia L Fernandez
Feb 26, 2011·Journal of Ethnopharmacology·Jian-Ping WangYun-Xia Wu
Apr 27, 2016·Journal of the American Chemical Society·Xuerong YuTuoping Luo
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 18, 2018·Nucleosides, Nucleotides & Nucleic Acids·Mamdouh A Abu-Zaied, Galal H Elgemeie
Oct 3, 2014·Basic & Clinical Pharmacology & Toxicology·Marilia Trindade de Santana SouzaLucindo José Quintans-Júnior
Sep 16, 2017·Chemical Reviews·You Yang, Biao Yu
Nov 3, 2010·Bioorganic & Medicinal Chemistry·Felix FlachsmannWilliam Fenical

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