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Synthesis of 1‐(4‐substituted)benzyl‐6‐hydroxyisoquinolines with potential activity on NA + ,K + ‐atpase
Author(s) -
Cerri Alberto,
Mauri Paola,
Mauro Marina,
Melloni Piero
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300622
Subject(s) - chemistry , ether , medicinal chemistry , group (periodic table) , isoquinoline , ring (chemistry) , stereochemistry , organic chemistry
The synthesis of 1‐(4‐substituted)benzyl‐6‐hydroxyisoquinolines, to be evaluated in the displacement of the specific 3 H‐ouabain binding to Na + ,K + ‐ATPase, is described. The key step involved a cyclization to the isoquinoline ring under Pictet‐Gams conditions which was best performed with the 6‐hydroxy group protected as the benzyl ether. When an unsaturated ester group was present in position 4 of the 1‐benzyl group, this was best introduced before the cyclization step, since the IIeck reaction on 1‐(4‐bromobenzyl)‐6‐hydroxyisoquinoline ( 8 ) with acrylic acid derivatives was not successful in all cases.