1621283-98-4Relevant articles and documents
Tailoring 3,3'-dihydroxyisorenieratene to hydroxystilbene: Finding a resveratrol analogue with increased antiproliferation activity and cell selectivity
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
, p. 8904 - 8908 (2014/07/22)
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 1 (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 1 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. 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 1 was concisely synthesized by a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity (see figure).
