Benzothiazolines are a class of heterocyclic compounds known for their diverse biological properties, as reported in the literature [1-2]. These properties have motivated extensive research to synthesize derivatives with enhanced and multiple biological activities.
Similarly, Schiff bases are well documented for their significant biological activity and diverse applications [3-5]. They remain a focus of research for the development of novel biologically active compounds.
In this study, we synthesized a Schiff base derivative of benzothiazolone, (E)-6-(((5-chloro-2-hydroxyphenyl)imino)methyl)-3-methylbenzo[d]thiazol-2(3H)-one, (1a), using a green chemistry approach. The reaction employed ultrasound-assisted synthesis in ethanol, resulting in an appreciable yield. Starting materials included 3-methyl-2-benzothiazolinone and 5-chloro-2-hydroxybenzaldehyde. The structure of SBM was confirmed using IR, ¹H NMR, and ¹³C NMR spectroscopic techniques.
Additionally, the pharmacokinetic and drug-likeness features of (1a) were evaluated using Lipinski's Rule of Five, a guideline that assesses a compound's potential as an orally active drug based on properties such as molecular weight, lipophilicity, and hydrogen bond donors/acceptors. The findings highlight the synthesized compound's potential biological relevance and suitability for further development.
[1] M. Erdogan et al., “Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer’s disease,” European J. of Med Chem, vol. 212, p. 113124, Feb. 2021, doi: 10.1016/j.ejmech.2020.113124.
[2] S. H. Ferreira, et al., “S14080, a peripheral analgesic acting by release of an endogenous circulating opioid‐like substance,” British J Pharmacology, vol. 114, no. 2, pp. 303–308, Jan. 1995, doi: 10.1111/j.1476-5381.1995.tb13227.x.
[3] N. Dharmaraj, et al., “Ruthenium(II) complexes containing bidentate Schi bases and their antifungal activity”.
[4] R. S. Joseyphus and M. S. Nair, “Antibacterial and Antifungal Studies on Some Schiff Base Complexes of Zinc(II),” Mycobiology, vol. 36, no. 2, pp. 93–98, Jun. 2008.
[5] A. Jarrahpour, et al., Molecules, vol. 12, no. 8, pp. 1720–1730, Aug. 2007, doi: 10.3390/12081720.
