Synthesis, in vitro Antimicrobial assay and Molecular Docking Studies of some new Symmetrical Bis-Schiff Bases and their 2-Azetidinones.

Sangar Ali Hassan; Media Noori Abdullah; Dara Muhammed Aziz

doi:10.21271/ZJPAS.33.2.4

Authors

Sangar Ali Hassan Department of Chemistry, College of Science, Raparin University-Sulaymaniyah, Kurdistan Region, Iraq
Media Noori Abdullah Department of Chemistry, College of Science, Salahaddin University - Erbil, Kurdistan Region, Iraq
Dara Muhammed Aziz Department of Chemistry, College of Science, Raparin University-Sulaymaniyah, Kurdistan Region, Iraq

DOI:

https://doi.org/10.21271/ZJPAS.33.2.4

Keywords:

Symmetrical Bis-Schiff Base, 2-Azetidinone, Antimicrobial assay, and Molecular Docking Studies.

Abstract

Four membered cyclic amides that are a broadly utilized class of antimicrobial agents up to now. Moreover, Symmetrical Bis-Schiff bases constitute an extraordinary class of strained compounds with varied applications and building blocks for the synthesis of 2-Azetidinones antibiotics. Because of those over biological significance, this study concludes a versatile synthetic precursor for the synthesis of the new Symmetrical Bis-Schiff bases and 2-Azetidinones in an exceedingly high yield. 2-Azetidinones were synthesized through [2+2] dichloroketene-imine cycloaddition reaction. The structures of the synthesized compounds were characterized by FT-IR, ¹H-NMR, and ¹³C-NMR. Additionally, the products were assayed against two antibacterial types Gram-positive (S. aureus) and Gram-negative (E. coli) microorganisms and two varieties of fungal strains A. niger, T. mentagrophytes by broth microdilution method. As a result, all synthesized compounds displayed good antimicrobial activities against resistant strains. Finally, molecular docking studies were explained the inhibitory activities for the new products with the target (PDB ID: 1MWU) methicillin acyl-Penicillin binding protein 2a from methicillin-resistant Staphylococcus aureus strain 27r at 2.60 Å resolution.

References

ABBAS, S., NASIR, H. H., ZAIB, S., ALI, S., MAHMOOD, T., AYUB, K., TAHIR, M. N. & IQBAL, J. 2018. Carbonic anhydrase inhibition of Schiff base derivative of imino-methyl-naphthalen-2-ol: Synthesis, structure elucidation, molecular docking, dynamic simulation and density functional theory calculations. Journal of Molecular Structure, 11 (5), 183-200.

AL-MASOUDI, W. A., FAAZ, R. A., AL-ASADI, R. H. & JABBAR, H. S. 2016. Synthesis, antimicrobial activity and modelling studies of some new metal complexes of Schiff base derived from sulphonamide drug in vitro. European Journal of Chemistry, 7 (1), 102-106.

ALI, A., GHANIM, H. T. & SAID, M. H. 2015. Synthesis and Identification of Schiff Bases lidands as derivatives for Terephthaldehyde and studies it is complexes with some elements Journal of Applied, Physical and Biochemistry Research, 1 (1), 9-16.

ANACONA, J., NORIEGA, N. & CAMUS, J. 2015. Synthesis, characterization and antibacterial activity of a tridentate Schiff base derived from cephalothin and sulfadiazine, and its transition metal complexes. Journal of Spectrochimica, 137 (14), 16-22.

AYYASH, A. N. 2019. A Novel Bioactive Compounds of 2-Azetidinone Derived from Pyrazin Dicarboxylic Acid: Synthesis and Antmicrobial Screening. Journal of Acta Pharmaceutica Sciencia, 57 (4), 103-114.

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, 22 (2), 128-154.

AZZAWI, A. M. A. & AL-OBIADI, K. K. H. 2016. Synthesis and Antimicrobial screening of new Bis-Schiff Bases and their Acetyl Oxadiazole Azetidinone derivatives derived from Pyromellitidiimide. International Journal of Research in Pharmacy and chemistry, 6 (1), 1-8.

BEG, M. & ATHAR, F. 2020. Pharmacokinetic and molecular docking studies of Achyranthes aspera phytocompounds to exploring potential anti-tuberculosis activity. Journal of Bacteriology & Mycology, 8 (1), 18-27.

BENDALE, A. R., BHATT, R., NAGAR, A., JADHAV, A. G. & VIDYASAGAR, G. 2011. Schiff base synthesis by unconventional route: an innovative green approach. Jornal of Der Pharma Chemica, 3 (2), 34-38.

BHUYAR, S., JUNEJA, H. & PAIWAL, L. 2013. Synthesis, spectroscopic and thermal studies of newly synthesized transition metal coordination polymers. Journal of Pharmaceutical, Biological and Chemical Sciences.Research Res. 20 (4), 557-564.

BORAZJANI, N., BEHZADI, M., DADKHAH ASEMAN, M., JARRAHPOUR, A., RAD, J. A., KIANPOUR, S., IRAJI, A., NABAVIZADEH, S. M., GHANBARI, M. M. & BATTA, G. 2020. Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates. Journal of Medicinal Chemistry Research, 5 (1), 1-21.

DA SILVA, C. M., DA SILVA, D. L., MODOLO, L. V., ALVES, R. B., DE RESENDE, M. A., MARTINS, C. V. & DE FÁTIMA, Â. 2011. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced research, 2 (1), 1-8.

DEEP, A., KUMAR, P., NARASIMHAN, B., LIM, S. M., RAMASAMY, K., MISHRA, R. K. & MANI, V. 2016. 2-Azetidinone derivatives: synthesis, antimicrobial, anticancer evaluation and QSAR studies. Journal of Acta Poloniae Pharmaceutica-Drug Research, 73 (1), 65-78.

ELSAYED, B. A., ELHENAWY, A. A. & SULTANAH, A. 2014. Synthesis, Characterization, Antimicrobial and Cytotoxic Studies on Some Novel Transition Metal Complexes of Schiff Base Ligand Derived From Sulfadiazine with Molecular Orbital Calculations. International Journal of Chemistry and Materials Research, 2 (1), 1-16.

HAMDAN, I. A.-A., HAMDAN, A. A.-A. & ALI, A. J. 2018. Synthesis, characterization and evolution of biological activity for new heterocyclic derivatives Schiff bases. Journal of Pharmaceutical Sciences and Research, 10 (7), 1710-1715.

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 (6), 92-109.

IBRAHIM, A. R. 2015. Preparation and Characterization of some transition metal complexes of bis Schiff Base Ligand. International Journal of Advanced Research, 8 (3), 315-324.

JURCIK, V., SLAWIN, A. M. & O'HAGAN, D. 2011. Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam. Beilstein journal of organic chemistry, 7 (1), 759-766.

KAJAL, A., BALA, S., KAMBOJ, S., SHARMA, N. & SAINI, V. 2013. Schiff bases: a versatile pharmacophore. Journal of Catalysts, 20 (3), 1-15.

KHAJAVI, M. 1998. Reaction of Imines with Trichloroacetic Esters or Anhydride Promoted by Iron Carbonyl or Microwave Irradiation. Preparation of 3, 3-Dichloro-β-Lactams. Journal of Chemical Research, 2 (1), 724-725.

KHDUR, R. A. & ZIMAM, E. H. 2018. Synthesis and Characterization of some new β-Lactam Derivatives from Azo Sulphadiazine and its Biological Evaluation as Anticancer. Journal of Oriental Chemistry, 34 (1), 371-380.

KHDUR, R. A. & ZIMAM, E. H. 2018. Synthesis, characterization and study biological screening of some new azetidinone derivatives from azo-sulphadiazine. Journal of Pak Biotechnol. 15 (2), 201-217.

KRATKY, M., DZURKOVA, M., JANOUSEK, J., KONECNA, K., TREJTNAR, F., STOLARIKOVA, J. & VINSOVA, J. 2017. Sulfadiazine salicylaldehyde-based Schiff bases: Synthesis, antimicrobial activity and cytotoxicity. Journal of Molecules, 22 (4), 1573-1588.

KRATKY, M., VINSOVA, J., VOLKOVA, M., BUCHTA, V., TREJTNAR, F. & STOLARIKOVA, J. 2012. Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold. European journal of medicinal chemistry, 50 (12), 433-440.

KUMAR, S., LIM, S. M., RAMASAMY, K., VASUDEVAN, M., SHAH, S. A. A., SELVARAJ, M. & NARASIMHAN, B. 2017. Synthesis, molecular docking and biological evaluation of bis-pyrimidine Schiff base derivatives. Journal of Chemistry Central, 89 (11), 1-16.

MEHTA, P., DAVADRA, P., PANDYA, J. R. & JOSHI, H. S. 2014. Synthesis, characterization and antimicrobial activity of 2-azetidinone derivatives of benzimidazoles. Journal of International Letters of Chemistry, Physics and Astronomy, 30 (11), 81-88.

MEHTA, P., SENGAR, N. P., SUBRAHMANYAM, E. V. & SATYANARAYANA, D. 2006. Synthesis and biological activity studies of some thiazolidinones and azetidinones. Indian journal of pharmaceutical sciences, 68 (1), 103-106.

MOHAMMED, H. A. & TAHA, N. I. 2017. Microwave Preparation and Spectroscopic Investigation of Binuclear Schiff Base Metal Complexes Derived from 2, 6-Diaminopyridine with Salicylaldehyde. International Journal of Organic Chemistry, 7 (4), 412-419.

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 (6), 3226-3234.

NOORI, N. S., ZAIDAN, T. A. & MESHER, M. F. 2019. Synthesis and Characterization of New Complexes for (1e,1'e)-N,N'-(Thiobis (4,1-Phenylene)) Bis(1-Phenylmethanimine) Substituted Ligands with Fe3+. International Research Journal Of Pharmacy, 9 (12), 57-63.

OZDEMIR GUNGOR, O. 2017. Intramolecular Proton Transfer Equilibrium in Salicylidene-and Naphthalene-based Tetraimine Schiff Bases. Journal of Science, 30 (1), 191-214.

PIENS, N. 2017. Synthesis of new β-lactam building blocks and their application in heterocyclic chemistry. Ph.D Dissertation, Ghent University.

SHARMA, R., SAMADHIYA, P., SRIVASTAVA, S. & SRIVASTAVA, S. 2012. Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine. Journal of Chemical Sciences, 12 (4), 633-637.

SHAYGAN, S., PASDAR, H., FOROUGHIFAR, N., DAVALLO, M. & MOTIEE, F. 2018. Cobalt (II) complexes with Schiff base ligands derived from terephthalaldehyde and ortho-substituted anilines: synthesis, characterization and antibacterial activity. Journal of Applied Sciences, 85 (8), 385-397.

SHINDE, A., ZANGADE, S., CHAVAN, S. & TİWDE, S. Yeni. 2015. Synthesis and antioxidant activity of some novel derivatives of bis-2-azetidinones and bis-4-thiazolidinones. Journal of the Turkish Chemical Society Section, 2 (4), 22-31.

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, 3 (2), 656-658.

SINGH, G. S. & SUDHEESH, S. 2014. Advances in synthesis of monocyclic beta-lactams. Journal of Arkivoc, 14 (1), 337-385.

SINGH, M., HAZRA, A., BHARITKAR, Y. P., KALIA, R., SAHOO, A., SAHA, S., RAVICHANDIRAN, V., GHOSH, S. & MONDAL, N. B. 2018. Synthesis of diversely substituted bis-pyrrolizidino/thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition. Royal Society Journal of Chemistry, 21 (8), 18938-18951.

TURAN, B., ŞENDIL, K., ŞENGÜL, E., GÜLTEKIN, M. S., TASLIMI, P., GULCIN, I. & SUPURAN, C. T. 2016. The synthesis of some β-lactams and investigation of their metal-chelating activity, carbonic anhydrase and acetylcholinesterase inhibition profiles. Journal of enzyme inhibition and medicinal chemistry, 31 (1), 79-88.

TURAN, N. & SEKERCI, M. 2009. Metal complexes of Schiff base derived from terephthalaldehyde and 2-amino-5-ethyl-1, 3, 4-thiadiazole synthesis, spectral and thermal characterization. Journal of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 39 (10), 651-657.

VAN BRABANDT, W., DEJAEGHER, Y. & DE KIMPE, N. 2005. New reactions of functionalized β-lactams. Journal of Pure and applied chemistry, 77 (12), 2061-2071.

ZIWAR, J. B. & MUSHEER, N. 2016. Synthesis of some Heterocyclic Compounds (Oxazepine, Diazepine) using Ultrasound Irradiation. ZANCO Journal of Pure And Applied Sciences, 28 (2), 235-239.