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Synthesis of novel trans-4-(phthalimidomethyl)- and 4-(imidazol-1-ylmethyl)-3-indolyl-tetrahydroisoquinolinones as possible aromatase inhibitors

Nikola T. Burdzhiev, Todor I. Baramov, Elena R. Stanoeva, Stanislav G. Yanev, Tsveta D. Stoyanova, Diana H. Dimitrova, and Kristina A. Kostadinova

Sofia University “St. Kliment Ohridski”, Faculty of Chemistry and Pharmacy, Sofia, Bulgaria

 

E-mail: nburdzhiev@chem.uni-sofia.bg

Abstract: The reaction of homophthalic anhydride with 1H-indol-3-carbaldimines was used for the preparation of trans- and cis-2-alkyl-3-indolyl-1-oxotetrahydroisoquinolin-4-carboxylic acids 3a–d. The stereochemistry of the reaction was investigated by means of 1H NMR spectroscopy. The carboxylic group of trans-3a–d was transformed stereoselectively via 4-hydroxymethyltetrahydroisoquinolin-1-ones into 4-(phthalimidomethyl)-derivatives trans-6a,b and 4-(imidazolylmethyl)-derivatives trans-8b–d. Compounds trans-6a,b and 8b–d were tested for antiaromatase activity, and the preliminary results showed that the phthalimidomethylisoquinolinone trans-6b at 50 μM concentration decreased the aromatase enzyme activity with 40%.

Keywords: Tetrahydroisoquinolinones ; Imidazoles ; Phthalimides ; Mitsunobu protocol ; Homophthalic anhydride ; Antiaromatase activity 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-00677-7

 

Chemical Papers 73 (5) 1263–1277 (2019)

Tuesday, September 17, 2019

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