Experimental and theoretical studies of 2-Mercaptobenzothiazole with 2-Bromomethylmesitylene and 1,4-Bis(bromomethyl)durene

• Published in: Journal of molecular structure 2020-12, Vol.1222, p.128894, Article 128894
• Main Authors: Daisy, Caroline, Asha, R. Nandini, Kumar, G.S. Suresh, Vadivel, E., Bhuvanesh, N., Nayagam, B. Ravindran Durai
• Format: Article
• Language: English
• Subjects: Benzothiazole; DFT; DNA binding; Hirshfeld surface analysis; Molecular docking; Weak bonding interactions
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.128894

•BTM1 and BTD2 were crystallized as a triclinic system and well associated.•DFT calculations revealed that BTD2 had higher stability than BTM1.•Molecular docking exposed BTM1 and BTD2 as efficient anti-cancer drugs.•DNA binding studies displayed that both benzothiazole compounds had hyperchromism and had good binding efficiency with CT-DNA.•When compared with BTD2, BTM1 exhibited good activity against the microbes that were taken for study. Biologically important 2-(2,4,6-trimethylbenzylthio)benzo[d]thiazole[BTM1] and 2-(4-((benzo[d]thiazol-2-ylthio)methyl)-2,3,5,6-tetramethylbenzylthio)benzo[d]thiazole [BTD2] were synthesized and characterised using FT-IR, NMR and single-crystal XRD (SCXRD). SCXRD revealed that both compounds were crystallized as a triclinic system and were associated through weak intermolecular interactions like H-bondings (CH…N, sp3-, and sp2-CH…π), π-π stackings and Vander Waals interactions. These weak intermolecular interactions in BTM1 and BTD2 were studied using Crystal Explorer and Gaussian. The interaction of title compounds with epidermal growth factor receptor (EGFR)tyrosine kinase protein was performed using AutoDock Vina. Molecular docking study revealed an efficient interaction of compounds with the protein resulting in good anti-cancer activity. DNA binding studies were explored against calf thymus (CT) DNA using a spectrophotometric titration method and was found that benzothiazole compounds showed hyperchromism and good binding efficiency. In-vitro anti-microbial activities against some bacterial and fungal strains were investigated. BTM1exhibited a better inhibition against bacterial (Bacillus subtilis and Staphylococcus aureus) and fungal (Aspergillus niger) strains than BTD2. [Display omitted]