Organic & Biomolecular Chemistry Blog

Terpenes and other polycycles are very common in nature and as many are biologically active, have been a key target for synthetic organic chemists. Rama Heng and Samir Zard from Ecole Polytechnique in France have demonstrated a general approach to polycyclic structures featuring the direct formation of six-, seven-, and eight-membered rings. This very powerful, yet concise and highly flexible, approach to both fused and bridged polycyclic structures overcomes the limitations imposed by intrinsically slow radical transformations, opening numerous synthetic opportunities. Our referees were very enthusiastic about this paper and we think you will be too – expect to see more about this exciting new method!

This HOT article is available free until 21st April 2011! Read it today in OBC.

A flexible, unified radical-based approach to polycyclic structures
Rama Heng and Samir Z. Zard
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB00024A

Researchers from Kaohsiung Medical University, Taiwan, have synthesised and tested a number of 2,3-diarylquinoline derivatives for anticancer activities, one of which showed significant potential preventing cell growth in certain cancer cell lines.

Cherng-Chyi Tzeng and colleagues synthesised the 2,3-diarylquinoline derivatives as part of a continuing study to explore potent anticancer drug candidates.  The quinoline skeleton is prevalent in many natural and synthetic heterocycles with a wide range of biological effects, including antitumor activity.  The structures of tamoxifen and combretastatin A-4, two potent anticancer agents, were modified to include the quinoline moiety and various side chains to improve their activity.

Testing against six cancer cell lines, including human hepatocelluar carcinoma, non-small cell lung cancer and breast cancer, revealed one compound that was more active than tamoxifen.  6-fluoro-2,3-bis{4-[2-(piperidin-1-yl)ethoxy]phenyl}quinoline-otherwise known in this paper as the more manageable 16b-was shown to induce cell cycle arrest at the G2/M phase, resulting ultimately in cell death in half of the tested cell lines.  Work is ongoing to optimise the structure.

This HOT article is free to access for the next month – download it today!

Synthesis and antiproliferative evaluation of 2,3-diarylquinoline derivatives
Chih-Hua Tseng, Yeh-Long Chen, Kuin-Yu Chung, Chi-Huei Wang, Shin-I Peng, Chih-Mei Cheng and Cherng-Chyi Tzeng
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB01225D