Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues

详细信息    查看全文

• 作者：Hongtao Xu^a ; Huanyu Tang^a ; Zhuo Yang^b ; Huijin Feng^a ; Yuanchao Li^a ; ^{ycli@mail.shcnc.ac.cn" class="auth_mail}
• 关键词：Diterpenoid ; Triptolide ; Triptonide ; Cytotoxic ; Synthesis
• 刊名：Tetrahedron
• 出版年：13 May, 2014
• 年：2014
• 卷：70
• 期：19
• 页码：3107-3115
• 全文大小：870 K

文摘

20-Hydroxytriptonide was synthesized from readily accessible l-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure-activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group.