Abstract:
: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.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Nimgirawath S,Udomputtimekakul P,Taechowisan T,Wanbanjob A,Shen Ydoi
10.1248/cpb.57.368subject
Has Abstractpub_date
2009-04-01 00:00:00pages
368-76issue
4eissn
0009-2363issn
1347-5223pii
JST.JSTAGE/cpb/57.368journal_volume
57pub_type
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