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New phenolphthalein-based surfactants were synthesized, and their antihyperlipidemic activity was evaluated through both  in vivo  and  in silico  investigations. The target compounds were synthesized using the O-alkylation reaction between phenolphthalein and different alkyl halides, i.e., decyl bromide (L-1), undecyl bromide (L-2), and dodecyl bromide (L-3). The structures of the synthesized surfactants were established through spectroscopic techniques such as IR,  1 H-NMR, and  13 C-NMR, as well as confirmed by mass spectrometry.  In vivo  experiments were conducted on rats with Triton-induced hyperlipidemia, and the results demonstrate a significant reduction in serum triglycerides, total cholesterol (TC), and glycerol (Gly), as well as an improvement in the high-density lipoprotein-cholesterol/TC ratio in hyperlipidemic rats treated with a dose of 100 mg/kg (L-1, L-2, and L-3) per body weight when compared with anti-hyperlipidemic drug. The new phenolphthalein surfactants showed an effective antihyperlipidemic activity, similar to that of the marketed drug. In addition,  in silico  molecular docking studies were performed to assess the interaction that can occur between the synthesized surfactants and the target SARS-CoV-2 N protein ( 5KKN ) involved in lipid metabolism. The achieved outcomes showed that the investigated surfactant derivatives had a strong affinity for the target proteins, supporting their  in vivo  antihyperlipidemic activity. The quantum chemical parameters of the molecules studied were calculated by calculations made at the HF level at the 6-31++G(d,p) level in gas and water phases.

Synthesis and characterization of surfactants derived from phenolphthalein: In vivo and in silico studies of their antihyperlipidemic effect