Investigating the impact of the fluorescence and anticancer activities of N-alkyl and alkyl-hydroxy methylphthalimide dithiocarbamates

A simple and reliable spectroscopic technique has been established for determining the N-Alkyl and Alkyl-hydroxy methylphthalimide dithiocarbamate moiety using elemental analysis, ESI mass, IR,¹H, ¹³C NMR, DTA, and TGA analysis. The approach is based on the interaction between N-chloro-methylphthalimide and Alkyl and Alkyl-hydroxy dithiocarbamate moiety to produce stable colorless dithiocarbamate molecules L¹–L³. All three ligands exhibited fluorescence properties. The ligands L¹ C₁₃ H₁₄ N₂ O₃ S₂ and L² C₁₈H₂₄N₂O₂S₂ were characterized using the SC-XRD technique. L¹ crystallizes in the monoclinic space group P 21/c, with unit cell parameters a = 7.212(5) Å, b = 23.852(5) Å, c = 8.147(5) Å, α = 90.000(5)°, β = 94.365(5)°, γ = 90.000(5)°, and Z = 4. The ligand L² C₁₈H₂₄N₂O₂S₂ crystallizes in monoclinic space group P 21/c with unit cell parameters a = 17.8094(7) Å, b = 7.8671(3) Å, c = 13.6819(5) Å, α = 90°, β = 103.688(4)°, γ = 90°, Z = 4. β angle of L¹ is 94.365(5)°, lesser than that of L² which is 103.688(4)° due to the presence of two carbon atom in L¹ while L² it is having six carbon atoms which has resulted in stretching in bond angle. Bond angle of L¹ of N(2)-C(10)-S(1) formed at 113.23(13) whereas in L² bond angle of N(2)-C(10)-S(1) formed at 124.09(11). For L², there was disorder in the ethyl substituent, which was modeled with two equivalent conformations with occupancies of 0.561(2)/0.439(2). Anticancer activity of L¹–L³ was also tested in cell lines of Prostate PC-3, Lung HOP-62, Lung NCI-H226, and Lung A549.