First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine

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	First Total Syntheses of (+/-)-Isopiline, (+/-)-Preocoteine, (+/-)-Oureguattidine and (+/-)-3-Methoxynordomesticine and the Biological Activities of (+/-)-3-Methoxynordomesticine
	Nimgirawath, Surachai 1; Udomputtimekakul, Phansuang 1; Taechowisan, Thongchai 2; Wanbanjob, Asawin 1; Shen, Yuemao 3
通讯作者	surachai@su.ac.th
	2009-04-01
发表期刊	CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN	0009-2363
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记录号	WOS:000264616800006
引用统计
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
推荐引用方式 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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