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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
Corresponding Authorsurachai@su.ac.th
2009-04-01
Source PublicationCHEMICAL & PHARMACEUTICAL BULLETIN
ISSN0009-2363
Volume57Issue:4Pages:368-376
AbstractA 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.
KeywordAlkaloid Aporphine Isoquinoline Synthesis Antimicrobial Anti-inflammatory Activity
Subject AreaChemistry, Medicinal ; Chemistry, Multidisciplinary ; Pharmacology & Pharmacy
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaPharmacology & Pharmacy ; Chemistry
WOS SubjectChemistry, Medicinal ; Chemistry, Multidisciplinary ; Pharmacology & Pharmacy
WOS IDWOS:000264616800006
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/5593
Collection离退休
Affiliation1.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
Recommended Citation
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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