A Facile Preparation of 1-(6-Hydroxyindol-1-yl)-2,2-dimethylpropan-1-one.

Accession number;03A0040967
Title;A Facile Preparation of 1-(6-Hydroxyindol-1-yl)-2,2-dimethylpropan-1-one.
Author; DEMOPOULOS V J (Aristotle Univ. Thessaloniki, Thessaloniki, Grc) NICOLAOU I (Aristotle Univ. Thessaloniki, Thessaloniki, Grc) ZIKA C (Aristotle Univ. Thessaloniki, Thessaloniki, Grc)
Journal Title;Chem Pharm Bull
Journal Code:G0504A
ISSN:0009-2363
VOL.51;NO.1;PAGE.98-99(2003)
Figure&Table&Reference;TBL.1, REF.11
Pub. Country;Japan
Language;English
Abstract;An effective synthesis of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one (4) was developed starting from 1H-indole (2). The key step involved suitable utilization of 4-(1-pyrrolidino)pyridine for the removal of the chloroacetyl moiety from chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester (3); a possible mechanism is, also, presented. Compound 4 might lead to selectively substituted derivatives, either on the phenolic-OH or the indolyl-NH, with putative biological interest. In this respect, we found that the core structure of 1H-indol-6-ol (1) possesses a degree of aldose reductase inhibitory potential, at a concentration of 100 .MU.M. (author abst.)
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