109741-34-6Relevant academic research and scientific papers
The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet-Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids
Bartel, Karin,Bracher, Franz,Geisslinger, Franz,Keller, Marco,Sauvageot-Witzku, Karl,Schaefer, Michael,Urban, Nicole
, p. 2716 - 2725 (2022/01/12)
We present a systematic investigation on an improved variant of the N-acyl-Pictet-Spengler condensation for the synthesis of 1-benzyltetrahydroisoquinolines, based on our recently published synthesis of N-methylcoclaurine, exemplified by the total syntheses of 10 alkaloids in racemic form. Major advantages are a) using ω-methoxystyrenes as convenient alternatives to arylacetaldehydes, and b) using the ethoxycarbonyl residue for both activating the arylethylamine precursors for the cyclization reaction, and, as a significant extension, also as protective group for phenolic residues. After ring closure, the ethoxycarbonyl-protected phenols are deprotected simultaneously with the further processing of the carbamate group, either following route A (lithium alanate reduction) to give N-methylated phenolic products, or following route B (treatment with excess methyllithium) to give the corresponding alkaloids with free N-H function. This dual use of the ethoxycarbonyl group shortens the synthetic routes to hydroxylated 1-benzyltetrahydroisoquinolines significantly. Not surprisingly, these ten alkaloids did not show noteworthy effects on TPC2 cation channels and the tumor cell line VCR-R CEM, and did not exhibit P-glycoprotein blocking activity. But due to their free phenolic groups they can serve as valuable intermediates for novel derivatives addressing all of these targets, based on previous evidence for structure-activity relationships in this chemotype.
Synthesis of some 1-(3-hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolines and their binding affinities to DA receptor subtypes
Pinna, G.A.,Cignarella, G.,Scolastico, S.,Porceddu, M.L.
, p. 55 - 60 (2007/10/02)
1-(3-hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxytetrahydroisoquinolines (3a-c), derived from the D1 selective antagonist S-bulbocapnine by cleavage of the bond between the 2 aromatic moieties, have been synthesized and their in vitro affinity towards D1 and D2 receptors evaluated.Of the compounds tested, the 2-methyl derivative 3a while showing poor affinity towards D1 receptors was able to inhibit the D2 radioligand 3H-raclopride binding by 60percent at 10-5 M.Conformational analysis allows reasonable explanations of the loss of D1-affinity of 3a with respect to the model. substituted 1-(3-hydroxy-4-methoxybenzyl)-6,7-methylenedioxytetrahydroisoquinoline / D1 and D2 receptor binding / bulbocapnine conformational analysis
Alkaloids of Cryptocarya phyllostemon
Cave, Andre,Leboeuf, Michel,Moskowitz, Henri,Ranaivo, Anissa,Bick, I. Ralph C.,et al.
, p. 2243 - 2263 (2007/10/02)
The known alkaloids (-)-antofine (1), dehydroantofine (5), (-)-cryptowoline (6), (-)-cryptowolidine (7), and (-)-cryptowolinol (8), were isolated from the New Caledonian lauraceous plant Cryptocarya phyllostemon, together with five new bases : two secophenanthroindolizidines, (-)-phyllostemine (2) and (-)-phyllosteminine (3), one pyrrolidinylacetophenone, (-)-phyllostone (4), and two quaternary tetrahydrobenzylisoquinolines, (+)-phyllocryptine (9) and (+)-phyllocryptonine (10).Chemical and spectroscopic methods were used for identification and structural investigation.A synthesis of phyllocryptonine has permitted its stereostructure to be determined.
