Synthesis of New Series Bis-3-Chloro-β-Lactam Derivatives from Symmetrical Bis-Schiff Bases as Effective Antimicrobial Agents with Molecular Docking Studies
Endeavoring to find a new type of antimicrobial agents, a new sequence of bis-Schiff bases and bis-3-cholro-β-lactams are synthesized. An astonishing class of strained compounds is part of the symmetrical bis-Schiff bases that has widespread applications and building blocks for the combination of bis-3-cholro-β-lactams antibiotics. Bis-3-cholro-β-lactams are synthesized through (Staudinger) [2+2] ketene-imine cycloaddition reaction. Structures of the produced compounds are deduced by 1H, 13C-NMR, and FT-IR spectroscopies. All produced compounds are shown moderate to good antimicrobial activity compared to human pathogenic bacteria strains (Escherichia coli and Staphylococcus aureus), also compared to Aspergillus Niger and Trichophyton mentagrophytes fungi through the broth microdilution technique. A molecular docking study is used for showing the active sides and binding affinity of the products with the target proteins or receptors of E. coli (PDB ID: 3GI9).
AL-AZZAWI, A. & AL-OBIADI, K. 2016. Synthesis and antimicrobial screening of new BisSchiff bases and their acetyl oxadiazole azetidinone derivatives from pyromellitic diimid. Int J Res Pharm & Chem, 6, 1-8.
ANACONA, J. & ACOSTA, F. 2006. Synthesis and antibacterial activity of cephradine metal complexes. Journal of Coordination Chemistry, 59, 621-627.
ANUSHA, K., KUMAR, Y. P., PRASAD, M. V. & GOPINATH, C. A review on 2-Azetidinones. Journal of Global Trends in Pharmaceutical Sciences, 6, 2388-2402.
ARSHAD, I., SAEED, A., CHANNAR, P. A., SHEHZADI, S. A., AHMED, M. N. & SIDDIQ, M. 2020. Bis-Schiff bases of 2, 2′-dibromobenzidine as efficient corrosion inhibitors for mild steel in acidic medium. RSC Advances, 10, 4499-4511.
AZIZ, D. M. & AZEEZ, H. J. 2020. Synthesis of new ß-lactam-N-(thiazol-2-yl) benzene sulfonamide hybrids: Their in vitro antimicrobial and in silico molecular docking studies. Journal of Molecular Structure, 1222, 128904.
BEG, M. & ATHAR, F. 2020. Pharmacokinetic and molecular docking studies of Achyranthes aspera phytocompounds to exploring potential anti-tuberculosis activity. J Bacteriol Mycol Open Access, 8, 18-27.
ESSA, H. H., KANDIL, F. & FALAH, A. 2012. Synthesis and identification of Schiff bases and bilogical activity new study. Iraqi Journal of Science, 53, 230-240.
HALVE, A., DUBEY, R., BHADAURIA, D., BHASKAR, B. & BHADAURIA, R. 2006. Synthesis, antimicrobial screening and structure-activity relationship of some novel 2-hydroxy-5-(nitro-substituted phenylazo) benzylidine anilines. Indian journal of pharmaceutical sciences, 68.
HASSAN, S. A. 2019. Synthesis, Spectroscopic study and Biological activity of some New Heterocyclic compounds derived from Sulfadiazine. Zanco Journal of Pure and Applied Sciences, 31, 92-109.
HASSAN, S. A. & AZIZ, D. M. 2021. Synthesis, in vitro Antimicrobial assay and Molecular Docking Studies of some new Symmetrical Bis-Schiff Bases and their 2-Azetidinones. Zanco Journal of Pure and Applied Sciences, 33, 34-50.
JARRAHPOUR, A., KHALILI, D., DE CLERCQ, E., SALMI, C. & BRUNEL, J. M. 2007. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules, 12, 1720-1730.
KAJAL, A., BALA, S., KAMBOJ, S., SHARMA, N. & SAINI, V. 2013. Schiff bases: a versatile pharmacophore. Journal of Catalysts, 2013, 1-14.
KAUR, R., SINGH, R., AHLAWAT, P., KAUSHIK, P. & SINGH, K. 2020a. Contemporary advances in therapeutic portfolio of 2-azetidinones. Chemical Biology Letters, 7, 13-26.
KAUR, R., SINGH, R., KUMAR, A., KAUR, S., PRIYADARSHI, N., SINGHAL, N. K. & SINGH, K. 2020b. 1, 2, 3-Triazole β-lactam conjugates as antimicrobial agents. Heliyon, 6, e04241.
KAUR, R., TRIPATHI, D., SINGH, K. & SINGH, R. 2018. Recent advances in β-lactam chemistry. Integrated Research Advances, 5, 52-57.
KHAN, K. M., KHAN, M., AMBREEN, N., RAHIM, F., MUHAMMAD, B., ALI, S., HAIDER, S. M., PERVEEN, S. & CHOUDHARY, M. 2011. Bis-Schiff bases of isatins: a new class of antioxidant. J. Pharm. Res, 4, 3402-3404.
KHAN, T., YADAV, R. & GOUND, S. S. 2018. An Efficient Synthesis and Antibacterial Activity of Some Novel 2‐Azetidinone Derivatives of 4H‐1, 2, 4‐Triazoles Under Mild Conditions. Journal of Heterocyclic Chemistry, 55, 1042-1047.
LIANG, C., LIU, Z., LIANG, Q., HAN, G.-C., HAN, J., ZHANG, S. & FENG, X.-Z. 2019. Synthesis of 2-aminofluorene bis-Schiff base and corrosion inhibition performance for carbon steel in HCl. Journal of Molecular Liquids, 277, 330-340.
MCLOUGHLIN, E., MEEGAN, M. & O’BOYLE, N. 2019. Stories from Staudinger: Synthesis of chiral beta-lactams, 5th International Electronic Conference on Medicinal Chemistry.
MÉNDEZ, L., POEYLAUT-PALENA, A. A. & MATA, E. G. 2018. Molecular diversity by olefin cross-metathesis on solid support. Generation of libraries of biologically promising β-lactam derivatives. Molecules, 23, 1193.
MOHATNTA, MISHRA, SAHU, MOHANTA & BANERJEE. 2014. Insilico designing of Pyrazol-1-Yl Azetidin-2-One derivatives as drug like molecules for possible inhibition of Anti Microbial 3GI9, 4AE5, 3FHU and 5COX target Proteins. International Journal of Drug Development and Research., 6, 78-91.
MY, N. H., HIRAO, H., VAN, D. U. & MOROKUMA, K. 2011. Computational studies of bacterial resistance to β-lactam antibiotics: mechanism of covalent inhibition of the penicillin-binding protein 2a (PBP2a). Journal of chemical information and modeling, 51, 3226-3234.
N’DRI, J. S., KABLAN, A., OUATTARA, B., KONÉ, M., OUATTARA, L., KODJO, C. G. & ZIAO, N. 2019. QSAR Studies of the Antifungal Activities of α-Diaminophosphonates Derived from Dapsone by DFT Method. Journal of Materials Physics and Chemistry, 7, 1-7.
NAZERUDDIN, K. P. A. G. M. 2016. synthesis characterization and antimicrobial evaluation of some novel bis schiff bases. Journal of Chemical and Pharmaceutical Research, 8, 906-911.
NWORIE, F. S. 2016. Bis (salicylidene) ethylenediamine (salen) and bis (salicylidene) ethylenediamine-metal complexes: From structure to biological activity. Journal of Analytical & Pharmaceutical Research, 3, 76-85.
PAGADALA, R., MESHRAM, J. S., CHOPDE, H. N. & JETTI, V. 2010. Synthesis of novel bis (β-Lactams) from bis (ketene) and imines. Inter. J. Chem. Tech. Pharma, 2, 1581-1585.
PATEL HM, RAJANI DP, SHARMA MG, BHATT HG, 2019. Synthesis, molecular docking and biological evaluation of mannich products based on thiophene nucleus using ionic liquid. Journal of Letters in Drug Design, 16, 119-126.
PETRUS, M., BOUWER, R., LAFONT, U., ATHANASOPOULOS, S., GREENHAM, N. & DINGEMANS, T. 2014. Small-molecule azomethines: organic photovoltaics via Schiff base condensation chemistry. Journal of Materials Chemistry A, 2, 9474-9477.
SHARMA, M., SAHU, N., KOHLI, D., CHATURVEDI, S. & SHARMA, S. 2009. Synthesis, Characterazation and biological activity of some 1-(Nicotinylamino)-2-substituted Azetidine-4-ones as potential Antibacterial agents. Digest Journal of Nanomaterials & Biostructures 4, 361-367.
SHINDE, A., ZANGADE, S., CHAVAN, S. & TİWDE, S. 2015. Yeni bis-2-azetidinon ve bis-4-tiyazolidinon türevlerinin sentezi ve antioksidan aktivitesi. Journal of the Turkish Chemical Society Section A: Chemistry, 2, 22-31.
SHNEINE, J., AL-ARAJI, Y. & SHAYEA, A. 2017. Synthesis of Bis-Heterocyclic Compounds and Study their Antimicrobial Activity. International Journal of Science and Research, 6, 1387-1392.
SHOCKRAVI, A., SADEGHPOUR, M. & OLYAEI, A. 2009. A convenient synthesis of novel symmetrical bis-Schiff bases of 2, 2'-thio-bis [4-methyl (2-aminophenoxy) phenyl ether] in solution and under solvent-free conditions. Journal of Chemical Research, 2009, 656-658.
TAHA, M., SAIN, A. A., ALI, M., RAHIM, F., ISMAIL, N. H., ADENAN, M. I., IMRAN, S., AL-HARRASI, A., NAWAZ, F. & IQBAL, N. 2020. Synthesis of symmetrical bis-Schiff base disulfide hybrids as highly effective anti-leishmanial agents. Bioorganic chemistry, 99, 103819.
TROISI, L., GRANITO, C. & PINDINELLI, E. 2010. Novel and recent synthesis and applications of β-lactams. Heterocyclic scaffolds I. Springer.
Copyright (c) 2021 Media N. Abdullah
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License [CC BY-NC-SA 4.0] that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work, with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online.