Development of novel conformation-constrained cytotoxic derivatives of cheliensisin A by embedment of small heterocycles
Deng, Xu1,3; Su, Jia1; Zhao, Yu1; Peng, Li-Yan1; Li, Yan1; Yao, Zhu-Jun2; Zhao, Qin-Shi1
Corresponding Authoryaoz@sioc.ac.cn ; qinshizhao@mail.kib.ac.cn
2011-09-01
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN0223-5234
Volume46Issue:9Pages:4238-4244
AbstractCheliensisin A is a natural styryl-lactone isolated from Goniothalamus cheliensis Hu in considerably large quantity with putative anticancer activities. However, its poor water solubility and chemical instability have precluded cheliensisin A as a potential drug candidate. To explore the strategy to overcome these problems, 21 novel derivatives of cheliensisin A with different substitutions at C-7 and C-8 positions were designed and synthesized. Inhibition of proliferation against five tumors cell lines indicates that eight new derivatives with embedment of oxazole or oxazoline exhibit improved cytotoxicity on SK-BR-3 and PANC-1, and compounds 2d and 2g show 5-8 folds higher potency than cisplatin. HPLC investigation of representative compounds indicates that oxazole and oxazoline analogs exhibit much improved chemical stability than their natural parent. (C) 2011 Elsevier Masson SAS. All rights reserved.
KeywordCheliensisin a Derivative Structure-activity Relationship Cytotoxicity Anticancer
Subject AreaChemistry, Medicinal
DOI10.1016/j.ejmech.2011.06.028
Indexed BySCI ; IC
Language英语
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000295237400074
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/3938
Collection中国科学院东亚植物多样性与生物地理学重点实验室
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 Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
3.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
Recommended Citation
GB/T 7714
Deng, Xu,Su, Jia,Zhao, Yu,et al. Development of novel conformation-constrained cytotoxic derivatives of cheliensisin A by embedment of small heterocycles[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2011,46(9):4238-4244.
APA Deng, Xu.,Su, Jia.,Zhao, Yu.,Peng, Li-Yan.,Li, Yan.,...&Zhao, Qin-Shi.(2011).Development of novel conformation-constrained cytotoxic derivatives of cheliensisin A by embedment of small heterocycles.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,46(9),4238-4244.
MLA Deng, Xu,et al."Development of novel conformation-constrained cytotoxic derivatives of cheliensisin A by embedment of small heterocycles".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 46.9(2011):4238-4244.
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