Green Synthesis Of New (E)-3-methyl-6-((naphthalene-1-ylimino)methyl)benzo[d]thiazol-2(3h)-one Schiff Base, ADME Study

The chemistry of heterocycles has received a great deal of attention in recent times due to their importance, and among these heterocycles is benzothiazolinone, which has received a great deal of attention due to its biological, pharmacological [1], [2], and agricultural [3] benefits.
Schiff bases, which are molecules whose structure contains imine functions (C=N), have also been the subject of constant attention and development due to their different biological properties [4], [5].
In this context, we synthesized an imine-benzothiazolinone molecule (E)-3-methyl-6-((naphthalen-1-ylimino)methyl)benzo[d]thiazol-2(3H)-one according to an environmentally friendly green chemistry approach using ultrasound in ethanol, which enabled the target compound to be recovered in high yield in a short and pure time without the need for purification techniques.
The structure of the compound was confirmed by IR, ¹H NMR and ¹³C NMR spectroscopic methods. Additionally, a study was conducted to examine the synthetic compound's pharmacological ADME properties based on lipinski's rule of five , revealing favorable drug-likeness characteristics and supporting its potential for further pharmaceutical development." .

References

[1] M. Ciba, F. Kaynak, S. Ozgen, et al., “Microwave Synthesis and Antimicrobial Evaluation of Mannich Bases of 6-Benzoyl-2(3H)-benzothiazolone,” Asian J. Chem..

[2] J.-Q. Weng, X.-H. Liu, H. Huang, C.-X. Tan, and J. Chen, “Synthesis, Structure and Antifungal Activity of New 3-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol-2(3H)-ones,” Molecules, vol. 17, no. 1, pp. 989–1001, Jan. 2012, doi: 10.3390/molecules17010989.

[3] “Elderfield, R.C. Heterocyclic Compounds; John Wiley & Sons: New York, NY, USA, 1957; p. 484.”.

[4] S. S. Tajudeen and G. Kannappan, “Schiff Base–Copper(II) Complexes: Synthesis, Spectral Studies and Anti-tubercular and Antimicrobial Activity,” Indian Journal of Advances in Chemical Science, 2016.

[5] A. Jarrahpour, D. Khalili, E. De Clercq, C. Salmi, and J. M. Brunel, “Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives,” Molecules, vol. 12, no. 8, pp. 1720–1730, Aug. 2007, doi: 10.3390/12081720.