中文版 | English
Title

Enantioselective semisynthesis of novel cephalotaxine esters with potent antineoplastic activities against leukemia

Author
Corresponding AuthorZhang,Qingwen; Zhang,Zhang; Li,Yingjun; Zhang,Xumu
Publication Years
2022-12-15
DOI
Source Title
ISSN
0223-5234
EISSN
1768-3254
Volume244
Abstract
Cephalotaxine-type alkaloids (CTAs), represented by homoharringtonine (HHT, 1), display potent efficacy against different types of leukemia cells. In this study, a method for hydrogenation of β-substituted itaconic acid monoesters with chiral Ru[DTBM-SegPhos](OAc) was developed. This metal-catalyzed asymmetric hydrogenation enabled the convenient semisynthesis of novel cephalotaxine derivatives with chiral 2′-substituted-succinic acid 4-mono-methyl esters as side chains. The preliminary structure-activity relationship (SAR) of the compounds' antineoplastic activities was studied. Eventually, we discovered compound 10b with potent antineoplastic activities against leukemia and broadly anticancer activities against a panel of cancer cells. Our study provided a highly enantioselective process enabling the semisynthesis of cephalotaxine derivatives, which are interesting for further study on a scientific basis.
Keywords
URL[Source Record]
Language
English
SUSTech Authorship
First ; Corresponding
Funding Project
Basic and Applied Basic Research Foundation of Guangdong Province[2020A1515110361];National Natural Science Foundation of China[81973158];National Natural Science Foundation of China[82150206];Universidade de Macau[MYRG2019-00150-ICMS];Ministry of Science and Technology of the People's Republic of China[SQ2019YFE010401];Shenzhen Bay Laboratory[SZBL2019062801006];
ESI Research Field
CHEMISTRY
Scopus EID
2-s2.0-85139735965
Data Source
Scopus
Citation statistics
Cited Times [WOS]:1
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/406561
DepartmentDepartment of Chemistry
前沿与交叉科学研究院
冷冻电镜中心
Affiliation
1.Academy for Advanced Interdisciplinary Studies,Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Department of Chemistry,and Medi-X Pingshan,Southern University of Science and Technology,Shenzhen,518000,China
2.International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE),Guangzhou City Key Laboratory of Precision Chemical Drug Development,School of Pharmacy,Jinan University,Guangzhou,510632,China
3.Shenzhen Bay Laboratory,Shenzhen,518132,China
4.Cryo-EM Center,Southern University of Science and Technology,Shenzhen,518055,China
5.State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences,University of Macau,999078,Macao
First Author AffilicationDepartment of Chemistry;  Academy for Advanced Interdisciplinary Studies
Corresponding Author AffilicationDepartment of Chemistry;  Academy for Advanced Interdisciplinary Studies
First Author's First AffilicationDepartment of Chemistry
Recommended Citation
GB/T 7714
Yang,Yujian,Yu,Qiuchun,Hu,Lean,et al. Enantioselective semisynthesis of novel cephalotaxine esters with potent antineoplastic activities against leukemia[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2022,244.
APA
Yang,Yujian.,Yu,Qiuchun.,Hu,Lean.,Dai,Botao.,Qi,Ruxi.,...&Zhang,Xumu.(2022).Enantioselective semisynthesis of novel cephalotaxine esters with potent antineoplastic activities against leukemia.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,244.
MLA
Yang,Yujian,et al."Enantioselective semisynthesis of novel cephalotaxine esters with potent antineoplastic activities against leukemia".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 244(2022).
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