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First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine
Nimgirawath, Surachai1; Udomputtimekakul, Phansuang1; Taechowisan, Thongchai2; Wanbanjob, Asawin1; Shen, Yuemao3
2009-04-01
发表期刊CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN0009-2363
卷号57期号:4页码:368-376
摘要A convenient and economical synthesis of 4-hydroxy-2,3-dimethoxybenzaldehyde has been developed. This was used as the starting material for the first total syntheses of (+/-)-isopiline, (+/-)-preocoteine, (+/-)-oureguattidine and (+/-)-3-methoxynordomesticine in which the key step involved formation of ring C of the aporphines by a radical-initiated cyclisation. Although (+/-)-3-methoxynordomesticine possesses weak antimicrobial activity, it inhibits the production of nitric oxide (NO), prostaglandin (PG)E-2, tumor necrosis factor (TNF)-alpha interleukin (IL)-1 beta and IL-6 and the expression of inducible nitric oxide synthase (iNOS) and cycloxygenase (COX)-2 in macrophages stimulated with LPS in vitro.
关键词Alkaloid Aporphine Isoquinoline Synthesis Antimicrobial Anti-inflammatory Activity
学科领域Chemistry, Medicinal ; Chemistry, Multidisciplinary ; Pharmacology & Pharmacy
收录类别SCI ; IC ; CCR
语种英语
WOS研究方向Pharmacology & Pharmacy ; Chemistry
WOS类目Chemistry, Medicinal ; Chemistry, Multidisciplinary ; Pharmacology & Pharmacy
WOS记录号WOS:000264616800006
引用统计
被引频次:7[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/5593
专题离退休
作者单位1.Silpakorn Univ, Dept Chem, Fac Sci, Nakhon Pathom 73000, Thailand
2.Silpakorn Univ, Dept Microbiol, Fac Sci, Nakhon Pathom 73000, Thailand
3.Chinese Acad Sci, Kunming Inst Bot, Kunming 650204, Peoples R China
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GB/T 7714
Nimgirawath, Surachai,Udomputtimekakul, Phansuang,Taechowisan, Thongchai,et al. First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine[J]. CHEMICAL & PHARMACEUTICAL BULLETIN,2009,57(4):368-376.
APA Nimgirawath, Surachai,Udomputtimekakul, Phansuang,Taechowisan, Thongchai,Wanbanjob, Asawin,&Shen, Yuemao.(2009).First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine.CHEMICAL & PHARMACEUTICAL BULLETIN,57(4),368-376.
MLA Nimgirawath, Surachai,et al."First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine".CHEMICAL & PHARMACEUTICAL BULLETIN 57.4(2009):368-376.
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