与厚朴酚和和厚朴酚相关的新型新木脂素的合成、细胞毒性及抗病毒活性
Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol.
作者信息
Amblard Franck, Govindarajan Baskaran, Lefkove Benjamin, Rapp Kimberly L, Detorio Mervi, Arbiser Jack L, Schinazi Raymond F
机构信息
Department of Pediatrics and Dermatology, Emory University School of Medicine, Atlanta, GA 30322, USA.
出版信息
Bioorg Med Chem Lett. 2007 Aug 15;17(16):4428-31. doi: 10.1016/j.bmcl.2007.06.024. Epub 2007 Jun 10.
Abstract
A series of new bisphenol derivatives bearing allylic moieties were synthesized as potential analogs of honokiol and/or magnolol. Certain compounds exhibited specific anti-proliferation activity against SVR cells and moderate anti-HIV-1 activity in primary human lymphocytes. Compound 5h was the most potent compound and its anti-tumor activity was evaluated in vivo.
摘要
合成了一系列带有烯丙基部分的新型双酚衍生物，作为厚朴酚和/或和厚朴酚的潜在类似物。某些化合物对SVR细胞表现出特定的抗增殖活性，在原代人淋巴细胞中具有中等的抗HIV-1活性。化合物5h是最有效的化合物，并对其体内抗肿瘤活性进行了评估。
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本文引用的文献
1
Facile purification of honokiol and its antiviral and cytotoxic properties.
J Med Chem. 2006 Jun 1;49(11):3426-7. doi: 10.1021/jm060268m.
2
Honokiol overcomes conventional drug resistance in human multiple myeloma by induction of caspase-dependent and -independent apoptosis.
Blood. 2005 Sep 1;106(5):1794-800. doi: 10.1182/blood-2005-01-0346. Epub 2005 May 3.
3
The natural product honokiol induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia (B-CLL) cells.
Blood. 2005 Jul 15;106(2):690-7. doi: 10.1182/blood-2004-11-4273. Epub 2005 Mar 31.
4
Cytotoxic neolignans: an SAR study.
Bioorg Med Chem Lett. 2005 Jan 3;15(1):163-6. doi: 10.1016/j.bmcl.2004.10.011.
5
Claisen rearrangement over the past nine decades.
Chem Rev. 2004 Jun;104(6):2939-3002. doi: 10.1021/cr020703u.
6
Efficient synthesis and structure-activity relationship of honokiol, a neurotrophic biphenyl-type neolignan.
Bioorg Med Chem Lett. 2004 May 17;14(10):2621-5. doi: 10.1016/j.bmcl.2004.02.067.
7
Metabolites of orally administered Magnolia officinalis extract in rats and man and its antidepressant-like effects in mice.
J Pharm Pharmacol. 2003 Nov;55(11):1583-91. doi: 10.1211/0022357022188.
8
Honokiol, a small molecular weight natural product, inhibits angiogenesis in vitro and tumor growth in vivo.
J Biol Chem. 2003 Sep 12;278(37):35501-7. doi: 10.1074/jbc.M302967200. Epub 2003 Jun 19.
9
Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.
Antimicrob Agents Chemother. 2002 Dec;46(12):3854-60. doi: 10.1128/AAC.46.12.3854-3860.2002.
10
Inhibition of MAP kinase kinase causes morphological reversion and dissociation between soft agar growth and in vivo tumorigenesis in angiosarcoma cells.
Am J Pathol. 2000 Dec;157(6):1937-45. doi: 10.1016/s0002-9440(10)64832-8.
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