Synthesis of 3'-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors.

Abstract

3'-Methoxy-E-diethylstilbestrol (2), with the structural and original similarities to 2-methoxyestradiol (2-ME2, 1), was synthesized and screened against HUVEC and a series of human cancer cell lines including RL95-2, SKOV-3, MCF-7 and T-47D in vitro. The configuration of the title compound was determined via the single crystal X-ray diffraction of its benzoyl-ester derivative (10). The fact that 3'-methoxy-E-diethylstilbestrol and its analogues (8 and 11) showed potential antiangiogenesis and anti-tumor activities at a close level, whereas its ester derivative (10) did not display any cytotoxic activities on all the screening cell lines indicated that the core scaffold of 3'-methoxy-3,4-diphenylhexane and the exposed hydroxyl-groups in the structures are essential pharmacophores for their anti-tumor activities.

• Authors: Qian Liu, Weiwei Jin, Yan Zhu, Jieyun Zhou, Min Lu, Qian Zhang
• Journal: Steroids (Steroids) Vol. 77 Issue 5 Pg. 419-23 (Apr 2012) ISSN: 1878-5867 [Electronic] United States
• PMID: 22280958 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2011 Elsevier Inc. All rights reserved.

Chemical References

• 3'-methoxy-E-diethylstilbestrol
• Angiogenesis Inhibitors
• Diethylstilbestrol

Topics

• Angiogenesis Inhibitors (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cells, Cultured
• Diethylstilbestrol (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• Drug Screening Assays, Antitumor
• Human Umbilical Vein Endothelial Cells (drug effects)
• Humans
• Inhibitory Concentration 50
• Models, Chemical
• Molecular Structure
• Neoplasms (blood supply, drug therapy, pathology)
• Structure-Activity Relationship
• X-Ray Diffraction