A facile preparation of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one.
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.
Demopoulos
Vassilis John
VJ
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Greece. vdem@pharm.auth.gr
Nicolaou
Ioannis
I
Zika
Chariklia
C
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors / Q000378:metabolism; D000818:Animals; D005260:Female; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051381:Rats; D011916:Rats, Inbred F344; D013678:Technology, Pharmaceutical / Q000379:methods*
D007211:Indoles; D000449:Aldehyde Reductase