Synthesis and characterization of binary compounds of the novel Azetidin-2-one ring and comparison of its biological activity

Duaa Jassim Ayed; Marwan Mohammed Farhan

doi:10.53730/ijhs.v6nS8.13206

Authors

Duaa Jassim Ayed
dua20s3007@uoanbar.edu.iq
Department Chemistry, College of Sciences, University Of Anbar, Ramadi 31007, Anbar, Iraq
Marwan Mohammed Farhan Department of Applied Chemistry, College of Applied Sciences-Hit, University Of Anbar, Hit 31007, Anbar, Iraq

Keywords:

β-lactams, Schiff base, antimicrobial, binary azetidin-2-one ring

Abstract

New organic compounds were prepared with two groups of azetidine-2-one, respectively.And that through the first two steps: New compounds were prepared with two groups of azomethine, by reacting benzaldehyde derivatives with primary amino compounds with di-amino groups. The result was diagnosed by following TLC, M.P, FT.IR.The second step: The azomethine compounds prepared in the previous step reacted with acetic acid dichloride with different molar numbers (1:2) and were diagnosed spectroscopically and physically by (TLC, M.P, FT.IR,H1NMR,C13.NMR.C.H.N.X.) to confirm the correctness of the structural formula of the resulting compounds. Finally, the effect of these prepared compounds on types of gram-positive and gram-negative bacteria (Escherichia Coli, Klebsiella pneumoniae, Staphylococcus aureus P.aeruginosa.) was studied and the results were compared with types of drugs available in pharmacies (Cefotaxime (C.C.X 10) 5 mg/ disc, Chloramphenicol (C.C.30) 30mg/ disc, Cefixime (C.F.M5) 10mg/ disc, Amoxicillin (A.M.C30) 30 mg/ disc). The results were very satisfactory against the growth of types of bacteria, and the reason was due to the increase in the number of azetidine-2-one rings, meaning the greater the number of these rings, the greater the killing of bacteria.

Downloads

Download data is not yet available.

References

Aguilar, L., Gimenez, M.J., Garcia-Rey, C. and Martin, J.E., 2002. New strategies to overcome antimicrobial resistance in Streptococcus pneumoniae with β-lactam antibiotics. Journal of Antimicrobial Chemotherapy, 50(suppl_3), pp.93-100.

Alcaide, B., Almendros, P. and Arangocillo, C., 2010. Highly reactive 4-membered ring nitrogen-containing heterocycles: synthesis and properties.

Aljamali, D.N.M. and Aljammali, D.Z.M., 2016. Survey on Beta–Lactam Drugs in Medicine. IOSRD International Journal of Medicine, 2(1), pp.6-10.

Al-Majidi, S.M. and Hama, L.H.K., 2015. Synthesis and antimicrobial evaluation activity of some new substituted spirothiazolidine, imidazolinone and azetidine derivatives of 5-bromo isatin. Journal of Zankoi Sulaimani, 17(1), pp.49-59.

Al-Majidi, S.M., Rasheed, H.M. and Al-Mugdadi, S.F.H., IjsSynthesis, Identification and Evaluation of Antimicrobial Activities of some New N-substituted 2-azetidinone, Imidazolidinone and tetrazole derivatives of 2-(methylthio) benzimidazole.

Asif, M., 2018. Antimicrobial potential of various substituted azetidine derivatives. MOJ Biorg Org Chem, 2(2), pp.36-40.

Cossio, F.P., Arrieta, A. and Sierra, M.A., 2008. The mechanism of the ketene− imine (Staudinger) reaction in its centennial: still an unsolved problem?. Accounts of chemical research, 41(8), pp.925-936.

Delpiccolo, C.M., Fraga, M.A. and Mata, E.G., 2003. An efficient, stereoselective solid-phase synthesis of β-lactams using Mukaiyama's salt for the staudinger reaction. Journal of Combinatorial Chemistry, 5(3), pp.208-210.

Desai, N.C., Pandya, D.D., Kotadiya, G.M. and Desai, P., 2014. Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles. Medicinal Chemistry Research, 23(4), pp.1725-1741.

Drew, W.L., Barry, A.L., O'Toole, R. and Sherris, J.C., 1972. Reliability of the Kirby-Bauer disc diffusion method for detecting methicillin-resistant strains of Staphylococcus aureus. Applied microbiology, 24(2), pp.240-247.

Geesala, R., Gangasani, J.K., Budde, M., Balasubramanian, S., Vaidya, J.R. and Das, A., 2016. 2-Azetidinones: Synthesis and biological evaluation as potential anti-breast cancer agents. European journal of medicinal chemistry, 124, pp.544-558.

Gilani, S.J., Khan, S.A., Alam, O., Singh, V. and Arora, A., 2011. Thiazolidin-4-one, azetidin-2-one and 1, 3, 4-oxadiazole derivatives of isonicotinic acid hydrazide: synthesis and their biological evaluation. Journal of the Serbian Chemical Society, 76(8), pp.1057-1067.

Jaberi, H.R., Fattahi, H., Ahmannasrollahi, A., Yarandpour, M. and Sedaghatizadeh, S., 2019. Synthesis of New 2-Azetidinone Derivatives and Related Schiff Bases from 3-Phenyl-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole. Organic Chemistry Research, 5(1), pp.42-50.

MahmoodHelmi, A.I., Mahdi, M.F. and Al-Smaism, R.F., Comparative studies on Conventional-Microwave assisted synthesis of 2-azetidinone derivatives.

Mandal, M.K., Ghosh, S., Bhat, H.R., Naesens, L. and Sin U.P., 2020. Synthesis and biological evaluation of substituted phenyl azetidine-2-one sulphonyl derivatives as potential antimicrobial and antiviral agents. Bioorganic Chemistry, 104, p.104320.

Mandal, M.K., Ghosh, S., Bhat, H.R., Naesens, L. and Singh, U.P., 2020. Synthesis and biological evaluation of substituted phenyl azetidine-2-one sulphonyl derivatives as potential antimicrobial and antiviral agents. Bioorganic Chemistry, 104, p.104320.

Olazaran, F.E., Rivera, G., Pérez-Vázquez, A.M., Morales-Reyes, C.M., Segura-Cabrera, A. and Balderas-Rentería, I., 2017. Biological Evaluation in vitro and in silico of Azetidin-2-one Derivatives as Potential Anticancer Agents. ACS medicinal chemistry letters, 8(1), pp.32-37.

Oliveira, P.F., Guidetti, B., Chamayou, A., André-Barrès, C., Madacki, J., Korduláková, J., Mori, G., Orena, B.S., Chiarelli, L.R., Pasca, M.R. and Lherbet, C., 2017. Mechanochemical synthesis and biological evaluation of novel isoniazid derivatives with potent antitubercular activity. Molecules, 22(9), p.1457.

Papp-Wallace, K.M., Docquier, J.D., Kerff, F. and Power, P., 2022. Structural and Biochemical Aspects of the Interaction of β-Lactamases With State-of-the-Art Inhibitors. Frontiers in Microbiology, 13.

Pawar, P.Y., Kalure, S.U. and Kulkarni, R.B., 2012. Synthesis and Pharmacological Screening of some new azetidinone derivatives. Int. J. Pharm. Sci, 4(5), pp.464-467.

Racha, U., 2016. Synthesis and Anti-Inflammatory Activity of Some New Schiff’s Bases and Azetidinones. International journal of science and research methodology, 4(3), pp.163-181.

Rajasekaran, A., Periasamy, M. and Venkatesan, S., 2010. Synthesis, characterization and biological activity of some novel azetidinones. J. Dev. Biol. Tissue Eng, 2(1), pp.5-13.

Swamy, P.V., Chandrasekhar, K.B. and Kambhampati, P.C., 2015. Synthesis and antibacterial activity of novel substituted azetidinones bearing 3, 4, 5-trimethoxy phenyl ring. Der Pharma Chemica, 7(6), pp.338-345.