Synthesis, characterization, in silico approach and in vitro antiproliferative activity of RPF151, a benzodioxole sulfonamide analogue designed from capsaicin scaffold

• Synthesis of RPF151, a benzo[d][1,3]dioxol-5-ylmethyl)butane-1-sulfonamide was reported.
• Characterization through FT-IR, 1H NMR, 13C NMR, CHN, melting point and X-ray methods.
• In silico molecular properties studies were compared to the experimental data.
• RPF151 demonstrated promising antiproliferative activity at low micromolar range.

RPF151, an alkylsulfonamide capsaicin analogue, was synthesized by a simple and efficient one-step methodology. The compound was characterized by 1H and 13C NMR, elemental analysis, IR and melting point. The crystal structure of RPF151 was determined by X-ray powder diffraction and its experimental arrangement was compared to the lowest-energy conformer from molecular dynamics simulation. The computational and experimental findings regarding the RPF151 structural arrangement have corroborated with one another. The compound was also tested in vitro against human umbilical vein endothelial cells (HUVEC) in order to verify its antiproliferative activity. RPF151 has significantly reduced the growth of HUVEC cells at 10 μM, suggesting that it probably would act on the angiogenesis process. RPF151 can be considered, then, as a promising anticancer lead for designing novel antitumor agents as potential drug candidates.

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