Synthesis, chiral resolution, and determination of novel furan lignan derivatives with potent anti-tumor activity

• Published in: Bioorganic & medicinal chemistry letters Vol. 20; no. 6; pp. 1961 - 1964
• Main Authors: Sun, Hai Ling, Wang, Tian Tian, Lv, Zhi Liang, Feng, Ji Lu, Geng, Dong Ping, Li, Yong Mei, Li, Ke
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 15.03.2010; Elsevier
• Subjects: Absolute configuration; Anticancer; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Chromatography, High Pressure Liquid; Circular dichroism spectra; Drug Screening Assays, Antitumor; Furan lignan; Furans - chemical synthesis; Furans - chemistry; Furans - pharmacology; General aspects; HeLa cell; HeLa Cells; Humans; Lignans - chemical synthesis; Lignans - chemistry; Lignans - pharmacology; Medical sciences; Models, Molecular; Pharmacology. Drug treatments; QGY-7701; Selectively hydrolization; Stereoisomerism; Circular dichroism spectra; Selectively hydrolization; Furan lignan; Absolute configuration; QGY-7701; HeLa cell; Anticancer; Antineoplastic agent; Human; Separation; Liver; Furan derivatives; Uterine cervix; In vitro; Hela cell line; Biological activity; Cell line; Optical resolution; Enantiomer; Circular dichroism spectrometry; Lignan; Chemical synthesis; Tumor cell; Structural analysis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2010.01.122

Two chiral furan lignan was synthesized, chiral separated and their absolute configuration was determined by circular dichroism spectra. Compound 2c (IC 50 = 12 μM on QGY-7701), the racemate of 2a and 2b, is reported. A kind of racemic furan lignans were synthesized via a novel route, and two optical isomers were obtained through a selective hydrolization. The absolute configurations were determined by circular dichroism spectroscopy after separated through a preparative column. The different activities of isomers and the racemates were evaluated on QGY-7701 and HeLa cell lines, and compound 2c showed the best activity on QGY-7701 and HeLa cell lines with IC 50 12 μM and 13 μM, respectively.