The Use of the Products of the Bijnelli Reaction as Nucleophiles for the Preparation of New Derivatives of Azetidine and the Evaluation of the Bacterial Effectiveness of the Resulting Compounds
Keywords:
azetidine, Pignelli reaction, biological activity
Abstract
This study produced new azetidine derivatives by reacting derivatives of
hydrazones (Benelli reaction products were used for this preparation) with chloroacetyl
chloride. The produced compounds were then identified using spectroscopic techniques
like infrared spectra (FT-IR) and resonance spectra (H1-NMR & C13-NMR). Among the
four bacterial isolates used to evaluate the biological efficacy of some of the prepared
compounds on their growth were Escherichia coli and Staphylococcus aureus. Thin layer
chromatography (TLC) was employed in addition to these analyses to monitor the
reactions' progress and ascertain the purity and melting points of the produced
compounds.
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Shukla, P., Deswal, D., & Narula, A. K. (2023). Antifungal activity of novel Azetidine tethered chitosansynthesized via Multicomponent reaction approach. Journal of Medical Mycology, 101409.
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Naser, A. W. (2013). Synthesis of Some New Heterocyclic Compounds Using α-(N-Saccharin) Acetohydrazide. Iraqi National Journal of Chemistry, 50, 199-206.
Pagani, N. R., Moverman, M. A., Puzzitiello, R. N., Menendez, M. E., Barnes, C. L., & Kavolus, J. J. (2021). Preoperative allergy testing for patients reporting penicillin and cephalosporin allergies is cost-effective in preventing infection after total knee and hip arthroplasty. The Journal of Arthroplasty, 36(2), 700-704.
Bijo, M., Mathew, G. E., Nirmal, M., & Vijayabaskaran, M. (2010). Synthesis, characterisation of some 2-azetidinone derivatives from 2-aminopyridine and evaluation of their antimicrobial activity. Der Pharma Chemica, 2(6), 238-242.
Sukhramani, P. S., Sukhramani, P. S., Tirthani, S. R., Desai, S. A., & Suthar, M. P. (2011). Biological cytotoxicity evaluation of spiro [azetidine-2, 3’-indole]-2’, 4 (1’H)-dione derivatives for anti-lung and anti-breast cancer activity. Der Pharmacia Lettre, 3(5), 236-243.
Shukla, P., Deswal, D., & Narula, A. K. (2023). Antifungal activity of novel Azetidine tethered chitosansynthesized via Multicomponent reaction approach. Journal of Medical Mycology, 101409.
Han, L., Zhao, W., Li, A., Zhou, B., Zhang, J., & Wu, W. (2022). Antifungal activity of l‐azetidine‐2‐carboxylic acid isolated from Disporopsis aspera rhizomes against Podosphaera xanthii. Pest Management Science, 78(5), 1946-1952.
Kusurkar, R. V., Rayani, R. H., Parmar, D. R., Patel, D. R., Patel, M. J., Pandey, N. O., ... & Soni, J. Y. (2023). Phenyl substituted 3-chloro 2-azetidinones: Design, green synthesis, antimicrobial activity, and molecular docking studies. Journal of Molecular Structure, 1272, 134185.
Rokde, V. V., Danao, K., Nimje, J., Nandurkar, D., Yerne, T., Yadav, P., & Mahajan, U. (2023). DESIGN, SYNTHESIS, ANTIMICROBIAL EVALUATION OF NOVEL 2‐OXO‐4‐SUBSTITUTED ARYL‐AZETIDINE BENZOTRIAZOLE DERIVATIVE. Chemistry & Biodiversity, e202300433.
Yue, P., Zhu, Y., Brotherton-Pleiss, C., Fu, W., Verma, N., Chen, J., ... & Turkson, J. (2022). Novel potent azetidine-based compounds irreversibly inhibit Stat3 activation and induce antitumor response against human breast tumor growth in vivo. Cancer letters, 534, 215613.
Imaizumi, T., Akaiwa, M., Abe, T., Nigawara, T., Koike, T., Satake, Y., ... & Kuramoto, K. (2022). Discovery and biological evaluation of 1-{2, 7-diazaspiro [3.5] nonan-2-yl} prop-2-en-1-one derivatives as covalent inhibitors of KRAS G12C with favorable metabolic stability and anti-tumor activity. Bioorganic & Medicinal Chemistry, 71, 116949.
Beatriz, A., Mondino, M. G., & de Lima, D. P. (2022). Lactams, Azetidines, Penicillins, and Cephalosporins: An Overview on the Synthesis and Their Antibacterial Activity. N-Heterocycles: Synthesis and Biological Evaluation, 97-142.
Rajulu, G. G., Naik, H. S. B., Kumar, G. C., Ramaraj, S., Sambasivam, G., & Koppolu, K. P. (2014). New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties. Medicinal Chemistry Research, 23, 2856-2868.
Layim, M. D., & Magtoof, M. S. (2022). Material design and biologically activity of some new azetidines and azetidine-2-ones as antioxident. Materials Today: Proceedings, 61, 878-886.
Dequina, H. J., Jones, C. L., & Schomaker, J. M. (2023). Recent updates and future perspectives in aziridine synthesis and reactivity. Chem.
Saleh, M. J., & Al-Badrany, K. A. (2023). Preparation, Characterization of New 2-Oxo Pyran Derivatives by AL2O3-OK Solid Base Catalyst and Biological Activity
Evaluation. Central Asian Journal of Medical and Natural Science, 4(4), 222-230.
Saleh, J. N., & Khalid, A. (2023). Synthesis, Characterization and Biological Activity Evaluation of Some New Pyrimidine Derivatives by Solid Base Catalyst AL2O3-OBa. Central Asian Journal of Medical and Natural Science, 4(4), 231-239.
Al-Joboury, W. M., Al-Badrany, K. A., & Asli, N. J. (2022, November). N-alkylation of substituted 2-amino benzothiazoles by 1, 4-bis (bromo methyl) benzene on mixed oxides at room temperature and study their biological activity. In AIP Conference Proceedings (Vol. 2394, No. 1). AIP Publishing.
Mohamed, S. A., Al-Badrany, K. A., & Huseen, M. S. (2022). PREPARATION AND STUDY OF BIOLOGICAL ACTIVITY OF PYRIMIDINE COMPOUNDS DERIVED FROM 2-ACETYLPYRIDINE. Vegueta. Anuario de la Facultad de Geografía e Historia, 22, 8.
Al-Hadidi, O. A. F., Al-Badrany, K. A., & Al-Bajari, S. A. (2022). Synthesis some of thiazepine compounds from 2-carbboxyaldehyde-5-methyl thiophene and study their biological activity on infected male rats epileptic. Journal of Education and Scientific Studies, 2(20).
Yang, X. B., Jia, C. H., Miao, X. Y., Li, Y. C., & Pang, S. P. (2023). Synthesis and characterization of potential polycyclic energetic materials using bicyclic triazole and azetidine structures as building blocks. RSC advances, 13(4), 2600-2610.
Layim, M. D., & Magtoof, M. S. (2023). Synthesis and Characterization of Some New Azetidines and Azetidine-2-Ones. HIV Nursing, 23(2), 695-699.
Shukla, P., Deswal, D., & Narula, A. K. (2023). Antifungal activity of novel Azetidine tethered chitosansynthesized via Multicomponent reaction approach. Journal of Medical Mycology, 101409.
Al-Joboury, W. M., Al-Badrany, K. A., & Asli, N. J. (2021). Synthesis of new azo dye compounds derived from 2-aminobenzothiazole and study their biological activity. Materials Today: Proceedings, 47, 5977-5982.
Al Rashidy, A. A. M., Al Badrany, K. A., & Al Garagoly, G. M. (2020, August). Spectrophotometric determination of sulphamethoxazole drug by new pyrazoline derived from 2, 4-dinitro phenyl hydrazine. In Materials Science Forum (Vol. 1002, pp. 350-359). Trans Tech Publications Ltd.
Al-Tufah, M. M., Jasim, S. S., & Al-Badrany, K. A. (2020). Synthesis and Antibacterial Evaluation of some New Pyrazole Derivatives. Prof.(Dr) RK Sharma, 20(3), 178
Published
2024-02-13
How to Cite
Hamad, D. T., Karim, M. G. A., & Jasim, S. S. (2024). The Use of the Products of the Bijnelli Reaction as Nucleophiles for the Preparation of New Derivatives of Azetidine and the Evaluation of the Bacterial Effectiveness of the Resulting Compounds. Central Asian Journal of Medical and Natural Science, 5(1), 600-607. Retrieved from https://cajmns.centralasianstudies.org/index.php/CAJMNS/article/view/2382
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