Structural Characterization and pharmacokinetic profile of boronic acid-functionalized bis-Schiff base
Abstract
A new bis-Schiff base molecule (E) derived from 1,5-diaminonaphthalene and 4-formylphenylboronic acid was synthesized via a condensation reaction and obtained in high yield. The molecular structure was unambiguously established by single-crystal X-ray diffraction analysis, revealing a centrosymmetric bis-imine framework crystallizing in the triclinic P-1 space group with DMF solvation. The azomethine (C=N) bond length confirms the formation of the imine linkage, while intermolecular O-H···O hydrogen bonds between boronic acid groups generate one-dimensional supramolecular chains in the solid state. The structure is further stabilized by CH···π and CH···O interactions. The compound was fully characterized by FT-IR and 1H/13C NMR spectroscopy and elemental analysis results were consistent with the calculated values. UV-Vis absorption and photoluminescence studies indicate the presence of an extended π-conjugated system. In silico pharmacokinetic evaluation using SwissADME suggests favorable drug-likeness, high predicted gastrointestinal absorption, and compliance with major drug-likeness rules. The combined structural, optical, and theoretical pharmacokinetic findings highlight the multifunctional potential of this boronic acid-functionalized Schiff base scaffold.
Keywords
Boronic acid, Pharmacokinetic properties, Schiff base, Single-crystal X-ray diffraction
Ethical Statement
References
- Lv, L., Zheng, T., Tang, L., Wang, Z., & Liu, W. (2025). Recent advances of Schiff base metal complexes as potential anticancer agents. Coordination Chemistry Reviews, 525, 216327. https://doi.org/10.1016/j.ccr.2024.216327
- Chaihan, K., Semakul, N., Promarak, V., Bui, T.-T., Kungwan, N., & Goubard, F. (2022). Tunable far-red fluorescence utilizing π-extension and substitution on the excited state intramolecular proton transfer (ESIPT) of naphthalene-based Schiff bases: A combined experimental and theoretical study. Journal of Photochemistry and Photobiology A: Chemistry, 431, 114047. https://doi.org/10.1016/j.jphotochem.2022.114047
- Mirtamizdoust, B., Karamad, A., Rahmani, N., Hanifehpour, Y., & Joo, S. W. (2023). Synthesis, characterization and DFT calculation of naphthalene-based crystal structure with pyridylimine-binding units. Crystals, 13(7), 1129. https://doi.org/10.3390/cryst13071129
- Burkhanova, T. M., Babashkina, M. G., Taskin-Tok, T., Sharov, A. V., & Safin, D. A. (2022). Naphthalene-based bis-N-salicylidene aniline dyes: Crystal structures, Hirshfeld surface analysis, computational study and molecular docking with the SARS-CoV-2 proteins. Journal of the Iranian Chemical Society, 19(6), 1979–1991. https://doi.org/10.1007/s13738-021-02438-y
- Karakaş, A., Elmali, A., Ünver, H., & Svoboda, I. (2004). Nonlinear optical properties of some derivatives of salicylaldimine-based ligands. Journal of Molecular Structure, 702(1–3), 103–110. https://doi.org/10.1016/j.molstruc.2004.06.017
- Lacroix, P. G. (2001). Second-order optical nonlinearities in coordination chemistry: The case of bis(salicylaldiminato)metal Schiff base complexes. European Journal of Inorganic Chemistry, 2001(2), 339–348. https://doi.org/10.1002/1099-0682(200102)2001:2
- Costes, J. P., Lamère, J. F., Lepetit, C., Lacroix, P. G., Dahan, F., & Nakatani, K. (2005). Synthesis, crystal structures, and nonlinear optical (NLO) properties of new Schiff-base nickel(II) complexes: Toward a new type of molecular switch? Inorganic Chemistry, 44(6), 1973–1982. https://doi.org/10.1021/ic048578n
- Matela, G. (2020). Schiff bases and complexes: A review on anti-cancer activity. Anticancer Agents in Medicinal Chemistry, 20(15), 1908–1917. https://doi.org/10.2174/1871520620666200507091207
- da Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B., & de Fátima, Â. (2011). Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2(1), 1–8. https://doi.org/10.1016/j.jare.2010.05.004
- Pandeya, S. N., Sriram, D., Nath, G., & De Clercq, E. (1999). Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl] thiosemicarbazide. European Journal of Pharmaceutical Sciences, 9(1), 25–31. https://doi.org/10.1016/S0928-0987(99)00038-X