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抗肿瘤药物。274. 安痛定和隐石松类似物 E 环 SAR 研究的新合成策略。

Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

机构信息

Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7568, USA.

出版信息

Org Lett. 2010 Apr 2;12(7):1416-9. doi: 10.1021/ol902819j.

DOI:10.1021/ol902819j
PMID:20196574
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2849728/
Abstract

A new versatile synthetic methodology for the synthesis of enantiomerically pure natural phenanthroindolizidines and phenanthroquinolizidines has been established and described. Natural products R-antofine and R-cryptopleurine, as well as a novel E-ring expanded analogue 13c (E7), 12-oxo-S-antofine (17), and 12N-methyl-12-aza-S-antofine (18) were synthesized with the new method. This strategy will greatly facilitate future SAR studies on the natural alkaloids with E-ring variations.

摘要

建立并描述了一种新的通用合成方法，用于合成对映体纯的天然菲并吲哚里嗪和菲并喹啉里嗪。利用新方法合成了天然产物 R-阿替非宁和 R-隐石松宁，以及一个新型 E 环扩展类似物 13c（E7）、12-氧代-S-阿替非宁（17）和 12N-甲基-12-氮杂-S-阿替非宁（18）。该策略将极大地促进未来对具有 E 环变化的天然生物碱的 SAR 研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/3378b8dc817c/nihms-184742-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/0d08bcf56ed7/nihms-184742-f0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/e2a192b991e6/nihms-184742-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/f9f0ea6b40fd/nihms-184742-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/424983efbcc0/nihms-184742-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/3378b8dc817c/nihms-184742-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/0d08bcf56ed7/nihms-184742-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/7a27a348c20e/nihms-184742-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/e2a192b991e6/nihms-184742-f0004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cdc4/2849728/3378b8dc817c/nihms-184742-f0007.jpg

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本文引用的文献

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Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.菲并吲哚里西啶和菲并喹诺里西啶：用于抗癌治疗的有前景的生物碱。
Curr Bioact Compd. 2009 Mar 1;5(1):2-19. doi: 10.2174/157340709787580928.
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Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.通过对映选择性分子内烯烃碳胺化反应全合成(S)-(+)-娃儿藤碱
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Total synthesis of phenanthroindolizidine alkaloids (+/-)-antofine, (+/-)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity.
将手性池方法应用于稀有的生物活性菲并喹嗪生物碱的噻吩类似物。
Tetrahedron. 2016 Jun 9;72(23):3221-3231. doi: 10.1016/j.tet.2016.04.047. Epub 2016 Apr 21.
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Total synthesis of (+)-antofine and (-)-cryptopleurine.（+）-安托非宁和（-）-隐脉叶番荔枝碱的全合成。
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Cryptopleurine analogs with modification of e ring exhibit different mechanism to rac-cryptopleurine and tylophorine.具有 E 环修饰的隐石松类似物表现出与拉卡隐石松和千里光菲灵不同的作用机制。
PLoS One. 2012;7(12):e51138. doi: 10.1371/journal.pone.0051138. Epub 2012 Dec 10.
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