Synthesis, molecular structure, spectroscopic characterization, NBO, NLO and NPA analysis and in vitro cytotoxicity study of 3-chloro-N-(4-sulfamoylphenethyl)propanamide with experimental and computational study

• The sulfonamide compound was synthesized and characterized crystallographically.
• Spectroscopic properties were compared experimentally and theoretically.
• DFT calculations were performed at B3LYP and B3PW91/6–311++G(d,p) level of theory.
• MEP and thermodynamic properties were also performed by DFT approach.
• The synthesized compound was evaluated for in vitro cytotoxic activity.

In present work, the sulfonamide compound, 3-chloro-N-(4-sulfamoylphenethyl)propanamide, has been synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, UV–vis and X-Ray single crystal determination. The compound crystallizes in the monoclinic space group P21/c with a = 8.4493(4) Å, b = 17.5875(7) Å, c = 9.2593(4) Å and β = 103.579(4)°, and Z = 4 in the unit cell. The molecular geometry from X-ray experiment in the ground state and vibrational frequencies, 1H and 13C-NMR chemical shifts, absorption wavelengths have been calculated by using the Density Functional Theory (DFT) method with 6–311++G(d,p) basis set and compared with the experimental values. In addition, Molecular Electrostatic Potential (MEP), Natural Bond Orbital (NBO), Frontier Molecular Orbital (FMO) analysis, thermodynamic properties, dipole moments, and HOMO-LUMO energy were also computed. The calculated results show that the optimized geometry can well reproduce the crystal structure parameters, and the vibrational frequencies, 1H and 13C-NMR chemical shifts, absorption wavelengths are in agreement with experimental values. Further, the synthesized compound was evaluated for in vitro cytotoxic activity against various tumour cells and normal cell line using MTT assay. The synthesized compound show the highest antiproliferative effect against ECC-1 tumour cells (IC50 = 0,167 mM), while the lowest cytotoxic activity against normal cell (HEK-293 and PNT1A) cell line (IC50 = 0.603 and 0.696 mM, respectively).

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