Tailoring 3, 3′‐Dihydroxyisorenieratene to Hydroxystilbene: Finding a Resveratrol Analogue with Increased Antiproliferation Activity and Cell Selectivity. Issue 29 (12th June 2014)

• Record Type: Journal Article
• Authors: Kang , Yan‐Fei; Yan , Wen‐Jing; Zhou , Ting‐Wen; Dai, Fang; Li, Xiu‐Zhuang; Bao, Xia‐Zhen; Du, Yu‐Ting; Yuan, Cui‐Hong; Wang, Hai‐Bo; Ren, Xiao‐Rong; Liu, Qiang; Jin, Xiao‐Ling; Zhou, Bo; Zhang, Jie
• Is Part Of: Chemistry. Volume 20:Issue 29(2014)
• Page Start: 8904
• Page End: 8908
• Publication Date: 2014-06-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201403024
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Four novel compounds were designed by "tailoring" 3, 3′‐dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule <bold>1</bold> (2, 3, 6, 2′, 3′, 6′‐hexamethyl‐4, 4′‐dihydroxy‐trans‐stilbene) was concisely synthesized in a one‐pot Stille–Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity mediated by blocking the NCI‐H460 cell cycle in G1 phase. Additionally, theoretical calculations and cell uptake experiments indicate that the unique polymethylation pattern of compound <bold>1</bold> significantly induces a conformational change shift out of planarity and increases its cell uptake and metabolic stability. The observation should be helpful to rationally design resveratrol‐inspired antiproliferative agents.</p> </abstract>