2-aminothiophene Schiff bases: Synthesis, characterization, Hirshfeld surface analysis, and their biological implications
The present study describes the synthesis and evaluation of novel 2-aminothiophene Schiff base compounds for potential cancer treatment applications. 2-Aminothiophene was synthesized using an adapted Gewald synthesis method and combined with salicylaldehyde to generate Schiff base derivatives. The molecular structures of the synthesized compounds were elucidated and confirmed using various analytical techniques. These included Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (¹H- and ¹³C-NMR), elemental analysis, and single-crystal X-ray diffraction (SC-XRD). Hirshfeld surface analysis revealed O…H as a significant contact for 1c, while 3c displayed notable O…H, C…H, C…C, and H…H contacts. Energy framework inspection confirmed that dispersion forces constitute the major packing contribution, with energies of -199.481 and -326.162 KJ/mol for 1c and 3c, respectively. Atomic charge and frontier molecular orbital analyses were performed using DFT calculations. The anticancer activities of the newly synthesized compounds were assessed using MTT cytotoxicity assays against two different cell lines: HCT-116 (colorectal carcinoma) and HepG2 (hepatocellular carcinoma). Several compounds demonstrated notable anticancer activity, characterized by low (IC₅₀) values, interestingly, compound 3d displayed low IC₅₀ values 4.86 µM against HCT-116 cell line approaching that doxorubicin (IC₅₀ = 3.07 µM). Notably, the Schiff base ligands exhibited improved cytotoxicity against HCT-116 compared to the parent 2-aminothiophene, with a safe profile against normal cell WI-38, highlighting their potential as promising cancer therapeutics.
The present study describes the synthesis and evaluation of novel 2-aminothiophene Schiff base compounds for potential cancer treatment applications. 2-Aminothiophene was synthesized using an…
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