Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol
Zhao, Yu1; Guo, Na1; Lou, Li-Guang2; Cong, Yu-Wen3; Peng, Li-Yan1; Zhao, Qin-Shi1
2008-05-01
Source PublicationBIOORGANIC & MEDICINAL CHEMISTRY
ISSN0968-0896
Volume16Issue:9Pages:4860-4871
AbstractTwenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22 mu M. 5-Oxo-13-TBDMS-taxchinin A (11) and5-oxo-13,15-epoxy-13-epi-taxchinin A (15) are the most potent derivatives, with IC(50) at 0.48 and 0.75 mu M, respectively. The structure - activity relationship (SAR) of these compounds established that exocyclic unsaturated ketone at ring C is the key structural element for the activity, while the alpha,beta-unsaturated ketone positioned at ring A has no effect for the activity. The significant cytotoxicity of derivatives 11 and 15 may be due to the conformational change in the taxane rings. The 3D-QSAR study was conducted on this series of compounds, which provided optimal predictive comparative molecular field (CoM-FA) model with cross-validated r(2) (q(2)) value of 0.64. (c) 2008 Elsevier Ltd. All rights reserved.
KeywordDerivatives Of Taxchinin a And Brevifoliol Synthesis Cytotoxicity Sar
Subject AreaBiochemistry & Molecular Biology ; Chemistry ; Medicinal ; Chemistry ; Organic
DOI10.1016/j.bmc.2008.03.041
Indexed BySCI
Language英语
WOS Research AreaBiochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry
WOS SubjectBiochemistry & Molecular Biology ; Chemistry, Medicinal ; Chemistry, Organic
WOS IDWOS:000255605600008
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/1913
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 200032, Peoples R China
3.Acad Mil Med Sci, Inst Radiat Med, Beijing 100850, Peoples R China
Recommended Citation
GB/T 7714
Zhao, Yu,Guo, Na,Lou, Li-Guang,et al. Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2008,16(9):4860-4871.
APA Zhao, Yu,Guo, Na,Lou, Li-Guang,Cong, Yu-Wen,Peng, Li-Yan,&Zhao, Qin-Shi.(2008).Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol.BIOORGANIC & MEDICINAL CHEMISTRY,16(9),4860-4871.
MLA Zhao, Yu,et al."Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol".BIOORGANIC & MEDICINAL CHEMISTRY 16.9(2008):4860-4871.
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