A facile preparation of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one |
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Authors: | Demopoulos Vassilis John Nicolaou Ioannis Zika Chariklia |
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Affiliation: | Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Greece. vdem@pharm.auth.gr |
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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 microM. |
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