劳伦二萜醇的全合成及绝对构型：一种缺氧诱导因子-1激活抑制剂
Total synthesis and absolute configuration of laurenditerpenol: a hypoxia inducible factor-1 activation inhibitor.
作者信息
Chittiboyina Amar G, Kumar Gundluru Mahesh, Carvalho Paulo B, Liu Yang, Zhou Yu-Dong, Nagle Dale G, Avery Mitchell A
机构信息
University of Mississippi. University, Mississippi 38677-1848, USA.
出版信息
J Med Chem. 2007 Dec 13;50(25):6299-302. doi: 10.1021/jm7011062. Epub 2007 Nov 16.
Abstract
The absolute stereo structure of the natural product laurenditerpenol (1S, 6R, 7S, 10R, 11R, 14S, 15R) has been accomplished from eight plausible stereoisomers by its first asymmetric total synthesis in a highly convergent and flexible synthetic pathway. Six stereoisomers of laurenditerpenol were synthesized and evaluated for their biological activity.
摘要
天然产物劳伦二萜醇（1S，6R，7S，10R，11R，14S，15R）的绝对立体结构已通过其首次不对称全合成，在一条高度汇聚且灵活的合成路线中，从八个可能的立体异构体中确定。合成了劳伦二萜醇的六个立体异构体，并对其生物活性进行了评估。
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本文引用的文献
1
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Cancer Metastasis Rev. 2007 Jun;26(2):341-52. doi: 10.1007/s10555-007-9059-x.
2
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Org Lett. 2007 Mar 29;9(7):1351-4. doi: 10.1021/ol070207y. Epub 2007 Mar 6.
3
Hypoxia: importance in tumor biology, noninvasive measurement by imaging, and value of its measurement in the management of cancer therapy.
Int J Radiat Biol. 2006 Oct;82(10):699-757. doi: 10.1080/09553000601002324.
4
Development of novel therapeutic strategies that target HIF-1.
Expert Opin Ther Targets. 2006 Apr;10(2):267-80. doi: 10.1517/14728222.10.2.267.
5
Pleiotropic effects of HIF-1 blockade on tumor radiosensitivity.
Cancer Cell. 2005 Aug;8(2):99-110. doi: 10.1016/j.ccr.2005.06.016.
6
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7
HIF-1 as a target for drug development.
Nat Rev Drug Discov. 2003 Oct;2(10):803-11. doi: 10.1038/nrd1199.
8
Targeting HIF-1 for cancer therapy.
Nat Rev Cancer. 2003 Oct;3(10):721-32. doi: 10.1038/nrc1187.
9
Convergent enantioselective synthesis of vinigrol, an architecturally novel diterpenoid with potent platelet aggregation inhibitory and antihypertensive properties. 1. Application of anionic sigmatropy to construction of the octalin substructure.
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10
The hypoxia-inducible factor-1 alpha is a negative factor for tumor therapy.
Oncogene. 2003 May 22;22(21):3213-20. doi: 10.1038/sj.onc.1206385.
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