Angiogenesis, Inflammation & Therapeutics | Online ISSN  2207-872X
RESEARCH ARTICLE   (Open Access)

Design, Synthesis, And Characterization Of New Schiff Bases For 3-Amino-1,2,4-Triazole-5-Thiolate Salt, Bearing Morpholine Ring And Biological Evaluation As Antibacterial Agents

Abeer Hussein Alia, and Mukhlif Mohsin Slaihimb*.

+ Author Affiliations

Journal of Angiotherapy 7(1) 1-9 https://doi.org/10.25163/angiotherapy.717333

Submitted: 04 March 2023  Revised: 23 July 2023  Published: 29 July 2023 

Antibacterial efficacy of new chemical compounds named benzaldehyde derivatives.

Abstract


Schiff bases (T1-T10) were prepared from the reaction of various benzaldehyde derivatives with 3-amino-1,2,4-triazole-5-thiol in the presence of Morpholine, and all the prepared compounds were characterized using UV, FIR spectroscopy, in addition to GC-Mass, 1H-NMR for some combinations and measuring their melting points. The obtained results confirmed the validity of the proposed structures of the prepared compounds. The biological activity of all prepared compounds (T1-T10) was tested against four types of Gram-positive and Gram-negative bacteria. The study showed that the compound T8 inhibited Staphylococcus aureus with an IC50 of 22 µg/mL, followed by T1, T10, T2, and T3 with IC50 values of 25, 26, 33, and 33 µg/mL, respectively. In addition, T3, T10, T2, T1, and T4 had an inhibitory effect on Pseudomonas aeruginosa with IC50 values of 22, 28, 39, 44, and 50 µg/mL, respectively. T4, T2, and T5 inhibited Streptococcus mutans with IC50 values of 28, 32, and 38 µg/mL, respectively. Interestingly, T6 had the strongest inhibitory effect on Klebsiella pneumoniae with an IC50 of 15 µg/mL. The results of this study suggest that T8, T3, T4, and T6 may be potential new antibiotics for the treatment of Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus mutans, and Klebsiella pneumoniae. However, further studies are needed to confirm these findings and to evaluate the safety and efficacy of these compounds in humans.

Keywords: 3-amino-1,2,4-triazole-5-thiol, morpholinium salt, Schiff base, antibacterial activity.

References


Amin, N. H., El-Saadi, M. T., Ibrahim, A. A., & Abdel-Rahman, H. M. (2021). Design, synthesis and mechanistic study of new 1, 2, 4-triazole derivatives as antimicrobial agents. Bioorganic chemistry, 111, 104841.

Arafath, M.A., Adam, F., Al-Suede, F.S.R., Razali, M.R., Ahamed, M.B.K., Majid, A.M.S.A., Hassan, M.Z., Osman, H. and Abubakar, S., 2017. Synthesis, characterization, X-ray crystal structures of heterocyclic Schiff base compounds and in vitro cholinesterase inhibition and anticancer activity. Journal of Molecular Structure, 1149, pp.216-228.

Chen, Y., Li, P., Su, S., Chen, M., He, J., Liu, L., ... & Xue, W. (2019). Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1, 2, 4-triazole Schiff base. RSC advances, 9(40), 23045-23052.

Dahham, S.S., Majid, A.M.S.A., Saghir, S.M. and Al suede, F.S., 2014. Antibacterial, antifungal, and antioxidant activities of Aquilaria crassna. Int J Adv Sci Technol, 2(3), pp.196-200.

Gupta, O., Pradhan, T., & Chawla, G. (2023). An updated review on diverse range of biological activities of 1, 2, 4-triazole derivatives: Insight into structure activity relationship. Journal of Molecular Structure, 1274, 134487.

Karrouchi, K., Chemlal, L., Taoufik, J., Cherrah, Y., Radi, S., Faouzi, M. E. A., & Ansar, M. H. (2016, November). Synthesis, antioxidant and analgesic activities of Schiff bases of 4-amino-1, 2, 4-triazole derivatives containing a pyrazole moiety. In Annales Pharmaceutiques Françaises (Vol. 74, No. 6, pp. 431-438). Elsevier Masson.

Khairuddean, M., Slaihim, M.M., Alidmat, M.M., Al-Suede, F.S.R., Ahamed, M.B.K., Shah, A.M. and Majid, A., 2020. Synthesis, characterisation of some new schiff base for the piperidinium 4-amino-5-substituted-4h-1, 2, 4-triazole-3-thiolate, and their in-vitro anticancer activities. Int. J. Natural Sci. Human Sciences., 1(1), pp.48-58.

Küçükgüzel, I., Küçükgüzel, S. G., Rollas, S., Ötük-Sanis, G., Özdemir, O., Bayrak, I., ... & Stables, J. P. (2004). Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1, 2, 4-triazole derivatives and their anticonvulsant activity. Il Farmaco, 59(11), 893-901.

Li, W., & Zhang, J. (2020). Synthesis of heterocycles through denitrogenative cyclization of triazoles and benzotriazoles. Chemistry–A European Journal, 26(52), 11931-11945.

Li, X., Li, X. Q., Liu, H. M., Zhou, X. Z., & Shao, Z. H. (2012). Synthesis and evaluation of antitumor activities of novel chiral 1, 2, 4-triazole Schiff bases bearing γ-butenolide moiety. Organic and medicinal chemistry letters, 2, 1-5.

Nahlé, A., Salim, R., El Hajjaji, F., Aouad, M. R., Messali, M., Ech-Chihbi, E., ... & Taleb, M. (2021). Novel triazole derivatives as ecological corrosion inhibitors for mild steel in 1.0 M HCl: experimental & theoretical approach. RSC advances, 11(7), 4147-4162.

Nalawade, T. M., Bhat, K. G., & Sogi, S. (2016). Antimicrobial activity of endodontic medicaments and vehicles using agar well diffusion method on facultative and obligate anaerobes. International Journal of clinical pediatric dentistry, 9(4), 335.

Neto, J. S., & Zeni, G. (2020). A decade of advances in the reaction of nitrogen sources and alkynes for the synthesis of triazoles. Coordination Chemistry Reviews, 409, 213217.

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