1226799-01-4Relevant academic research and scientific papers
Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans
Goel, Atul,Kumar, Amit,Hemberger, Yasmin,Raghuvanshi, Ashutosh,Jeet, Ram,Tiwari, Govind,Knauer, Michael,Kureel, Jyoti,Singh, Anuj K.,Gautam, Abnish,Trivedi, Ritu,Singh, Divya,Bringmann, Gerhard
, p. 9583 - 9592 (2013/01/16)
A convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD calculations. (-)-Medicarpin and (-)-9-demethoxymedicarpin are both 6aR,11aR-configured, and consequently the corresponding enantiomers, (+)-medicarpin and (+)-9-demethoxymedicarpin, possess the 6aS,11aS-configuration. A comparative mechanism study for osteogenic (bone forming) activity of medicarpin (racemic versus enantiomerically pure material) revealed that (+)-(6aS,11aS)-medicarpin (6a) significantly increased the bone morphogenetic protein-2 (BMP2) expression and the level of the bone-specific transcription factor Runx-2 mRNA, while the effect was opposite for the other enantiomer, (-)-(6aR,11aR)-medicarpin (6a), and for the racemate, (±)-medicarpin, the combined effect of both the enantiomers on transcription levels was observed. The Royal Society of Chemistry 2012.
SUBSTITUTED BENZFUROCHROMENES AND RELATED COMPOUNDS FOR THE PREVENTION AND TREATMENT OF BONE RELATED DISORDERS
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, (2010/06/11)
The present invention relates to novel substituted benzfurochromenes and related compounds having the general formula (I), salts and chiral, achiral derivatives thereof; wherein R1, R2, R3, R4, R5, R
