异黄酮中的多种氢化物还原途径。
Multiple hydride reduction pathways in isoflavonoids.
作者信息
Salakka Auli K, Jokela Tuija H, Wähälä Kristiina
机构信息
Department of Chemistry, Laboratory of Organic Chemistry, P.O. Box 55, FIN-00014 University of Helsinki, Finland.
出版信息
Beilstein J Org Chem. 2006 Aug 25;2:16. doi: 10.1186/1860-5397-2-16.
BACKGROUND
Isoflavonoids are of interest owing to their appearance in metabolic pathways of isoflavones, and their estrogenic and other physiological properties, making them promising lead compounds for drug design.
RESULTS
The reduction of isoflavones by various hydride reagents occurs by a 1,4-pathway in contrast to ordinary beta-alkoxy-alpha,beta-unsaturated ketones. Isoflavan-4-ones, cis- and trans-isoflavan-4-ols, alpha-methyldeoxybenzoins or 1,2-diphenylprop-2-en-1-ols are obtained depending on the hydride reagent, mostly in good yields. The stereoselective reduction of isoflavan-4-ones is also discussed.
CONCLUSION
The work described in this paper shows that most structural types of reduced isoflavonoids are now reliably available in satisfactory or good yields by hydride reductions to be used as authentic reference compounds in analytical and biological studies.
背景
异黄酮类化合物因其在异黄酮代谢途径中的出现、雌激素及其他生理特性而备受关注，这使其成为药物设计中颇具潜力的先导化合物。
结果
与普通的β - 烷氧基 - α,β - 不饱和酮不同，各种氢化物试剂对异黄酮的还原通过1,4 - 途径进行。根据氢化物试剂的不同，可得到异黄烷 - 4 - 酮、顺式和反式异黄烷 - 4 - 醇、α - 甲基脱氧安息香或1,2 - 二苯基丙 - 2 - 烯 - 1 - 醇，大多产率良好。文中还讨论了异黄烷 - 4 - 酮的立体选择性还原。
结论
本文所述工作表明，通过氢化物还原，大多数结构类型的还原异黄酮类化合物现在都能以令人满意或良好的产率可靠地获得，可作为分析和生物学研究中的真实参考化合物。
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