Abstract
•Synthesis and characterization studies of four dihydroisoquinoline imines.•Structure of compound 2b was established by single X-ray crystallography.•In vitro angiotensin converting enzyme (ACE) was studied.•Docking of inhibitors in the active site of ACE.•The significant biological effect of the presence of chloro group in this class of compounds.
The different functionalities of imine group found in many compounds are of important biological activity. Since, the development of novel imines is biologically encouraged, this study aims to develop a straightforward synthesis pathway of dihydroisoquinoline imines that could reveal antihypertensive effects. Starting from 2-méthyl-1-phényl-2-propanol, four different dihydroisoquinoline imines compounds (2a-d) were obtained and their structures were analyzed by mass spectrum, elemental analysis and NMR spectral studies. The crystal structure of 2b was determined from single crystal X-ray diffraction data.
The newly synthesized compounds were evaluated for angiotensin I-converting enzyme (ACE) inhibition, using an enzymatic in vitro assay. The results were compared to Captopril as a reference drug. Compounds 2a, 2b and 2d showed inhibition activity with IC50 values of 0.15, 0.13 and 0.40 mg/ml, respectively. The docking of chemical compounds in the ACE active site explained the higher inhibitory capability of compounds 2a and 2b on the catalytic activity of the enzyme, indicating a potential anti-hypertensive effect of these compounds.
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