Synthesis and Antimonoamine Oxidase Activity of 2-(3-Iminoisoindol-1-ylidene)-2-arylacetonitriles

• Published in: Russian journal of organic chemistry Vol. 58; no. 5; pp. 663 - 668
• Main Authors: Grigor’eva, A. I., Shetnev, A. A., Kotov, A. D., Ivanovskii, S. A., Petzer, A., Petzer, J. P.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-05-2022; Springer Nature B.V
• Subjects: Acetic acid; Acetonitrile; Chemistry; Chemistry and Materials Science; Organic Chemistry; Oxidase; Synthesis; phthalonitrile; isoindole; condensation; arylacetonitriles; cascade reaction; MAO inhibition
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428022050049

A one-pot synthesis of 2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles in yields of up to 95% by the cascade condensation of phthalonitrile with arylacetonitriles in a superbasic NaOH/DMSO medium was proposed. A method for the synthesis of (
E
)-2-(3-oxoisoindol-1-ylidene)-2-arylacetonitriles by the hydrolysis of 2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles in acetic acid was developed. The obtained (
E
)-2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles were shown to be active inhibitors of human monoamine oxidase [IC
50
(MAO-A) for (
E
)-2-(3-iminoisoindol-1-ylidene)-2-(4-methylphenyl)acetonitrile 3.26 µM].