Synthesis and Biological Activity of 1-(4-Substituted Phenyl)-1-Alkyl(Aryl)-2-Phenyl-3-Aminopropan-1-Ol Hydrochlorides

• Published in: Pharmaceutical chemistry journal Vol. 49; no. 5; pp. 313 - 318
• Main Authors: Gasparyan, N. K., Mardanyan, S. S., Vermishyan, I. G., Antonyan, A. A., Paronikyan, R. V., Panosyan, G. A., Gevorgyan, G. A.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-08-2015
• Subjects: Medicine; Organic Chemistry; Pharmacology/Toxicology; Pharmacy; aminopropiophenones; aminomethylation; aminopropan-1-ols; adenosine deaminase (ADA) inhibitors
• ISSN: 0091-150X; 1573-9031
• DOI: 10.1007/s11094-015-1276-y

1-(4-Substituted phenyl)-2-phenylethanones were aminomethylated with paraformaldehyde and amine in ethanol to produce α-phenyl-β-amino-4-substituted propiophenones. Interaction of these with Grignard reagents in ether yielded tertiary aminopropan-1-ols and their hydrochlorides. Quite efficient inhibition, at differing levels, of adenosine deaminase (ADA, E.C. 3.5.44), one of the key enzymes in purine metabolism, by the compounds synthesized here was demonstrated. A structure-activity relationship was found for ADA inhibition. Most of the compounds synthesized here were found to lack antibacterial activity; only compounds Va, Vd, and VId displayed moderate levels of antibacterial activity against Gram-positive microorganisms.