128437-99-0Relevant articles and documents
SELECTED CGRP ANTAGONISTS, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICAMENTS
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Page/Page column 227, (2008/06/13)
The invention relates to CGRP antagonists of general formula (I), in which A, X, D, E, G, M, Q and R1 to R3 are defined as in Claim 1, to their tautomers, isomers, diastereomers, enantiomers, hydrates, mixtures and their salts as well as the hydrates of the salts, particularly their physiologically compatible salts having inorganic or organic acids, to medicaments containing these compounds, to their use, and to methods for the production thereof.
46. Mammalian Alkaloids: O-Methylation of (+/-)-Norcoclaurine-1-carboxylic Acid and Related Isoquinolines Including (S)- and (R)-Norcoclaurine with 14C-Labeled S-Adenosyl-L-Methionine in Presence of Mammalian Catechol O-Methyltransferase
Sekine, Yasuo,Creveling, Cyrus,Bell, Maureen,Brossi, Arnold
, p. 426 - 432 (2007/10/02)
(+/-)-Norcoclaurine-1-carboxylic acid (5) and the derived dihydroisoquinolinone 6 (present as quinonemethide 6a at pH 7) afforded, on methylation with 14C-labeled S-adenosyl-L-methionine in the presence of mammalian catechol O-methyltransferase, exclusively the 7-O-methylated congeners 7 and 9, respectively.High stereoselectivity of the O-methylation was observed with (-)-(S)- and (+)-(R)-norcoclaurine (2a and 2b, resp.), affording 80percent of 6-O-methylated isoquinoline 12 and 20percent of the 7-O-methylated isomer 11 from 2a, and the reversed proportion of 12 and 11 from 2b.Synthesis of the reference amino acid 8 was achieved by Pictet-Spengler condensation of O-benzyl-protected dopamine 17 with benzyl-protected keto acid 20 (-> 21) followed by methylation with diazomethane (-> 22 + 23) and removal of the protecting groups by acid hydrolysis.It is considered unlikely that amino acids such as 5 constitute important precursors in the biosynthesis of isoquinolines related to reticuline.