Synthesis of new N-acryl-1-amino-2-phenylethanol and N-acyl-1-amino-3-aryloxypropanols and evaluation of their antihyperlipidemic, LDL-oxidation and antioxidant activity

•We have synthesized fifteen new N-acyl-1-amino-2-alcohols, related to Aegeline.•All were screened for lipid lowering, LDL-oxidation and antioxidant activity.•Compounds 3, 11, 13 showed drug like lipid lowering, LDL-oxidation and antioxidant activity.

As a part of our drug discovery program, we identified an alkaloidal amide i.e. Aegeline (V) isolated from the leaves of Aegle marmelos as a dual acting agent (antihyperlipidemic and antihyperglycemic). In continuation of this program, we synthesized new N-acyl-1-amino-2-alcohols (N-acrylated-1-amino-2-phenylethanol and N-acylated-1-amino-3-aryloxypropanols) via Ritter reaction and screened for their in-vivo antihyperlipdemic activity in Triton induced hyperlipidemia model, LDL-oxidation and antioxidant activity. Compounds 3, 11 and 13 showed good antihyperlipidemic activity, LDL-oxidation as well as antioxidant activity and comparable activity with marketed antidyslipidemic drug.

Graphical abstractNew N-acyl-1-amino-2-alcohols (3 and 8–21) were synthesized and evaluated their antihyperlipdemic, LDL-oxidation and antioxidant activity. Compounds 3, 11 and 13 showed comparable activity with marketed antidyslipidemic drug.Figure optionsDownload full-size imageDownload as PowerPoint slide