Synthesis and Characterization of New Acrylamide Derivatives and Studying Their Antibacterial Activity

Authors

  • Ruaa M. Dhedan Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0003-1293-6706
  • Sana H. Awaad Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad, Iraq.
  • Suha. N. Fadhl Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad, Iraq.

DOI:

https://doi.org/10.21123/bsj.2024.8556

Keywords:

Acrylamide, Antibacterial activity, Heterocyclic compounds, Oxazepine, Schiff s bases.

Abstract

This study aims to test the new derivatives of polymers on the biological activities of two types of bacteria work describes the synthesis of 1,3-oxazepine and self-polymerization via a cycloaddition reaction between Schiff’s bases 2-methyl-N-(5-(2-methylbutanoylimino) pentylidene)but-2-enamide and succinic, maleic anhydride. The synthesized compounds were characterized by melting points, softening points, and physical properties such as swelling capacity, TGA, and FT-IR. The biological activity showed intermediate results against two bacterial isolates resistant to antibiotics.

References

Hansen BG, Munn SJ, Luotamo M, Musset C, Bruijn J de, Pakalin SF, et al. European Union Risk Assessment Report-Acrylamide Luxembourg. European Union Risk Assessment Report Acrylamide . United Kingdum: Office for Official Publications of the European Communities; 2002; 24: 1-221.

Zhang K, Chen S, Chang M, Du J, Yuan Z, Wang Y, et al. Treatment of polyacrylamide production wastewater by multistage contact reactor with activated and anammox sludge. Bioch Eng J. 2019 Oct 15; 150: 1-29. https://doi.org/10.1016/j.bej.2019.107287.

Agrimonti C, Lauro M, Visioli G. Smart agriculture for food quality: Facing climate change in the 21st century. Crit Rev Food Sci. 2021 Mar 26; 61(6): 971-981. https://doi.org/10.1080/10408398.2020.1749555

Derardja AA, Golea L, Benali-Cherif R, Luneau D, Boutobba Z, Boumedjane Y,et al. Synthesis, crystal structure, DFT calculations, Hirshfeld surface analysis and molecular docking studies of a new manganese complex. Inorg Chem Commun. 2022 Des; 146(10) :1-33. https://doi.org/10.1016/j.inoche.2022.110198

Venugopala KN, Kandeel M, Pillay M, Deb PK, Abdallah HH, Mahomoodally MF, et al. Anti-Tubercular Properties of 4-Amino-5-(4-Fluoro-3-Phenoxyphenyl)-4 H-1, 2, 4-Triazole-3-Thiol and Its Schiff Bases: Comput Input and Molec Dynam. Antibiotics. 2020 Aug 31; 9(9): 1-16. https://doi.org/10.3390/antibiotics9090559

Chen Y, Li P, Su S, Chen M, He J, Liu L, et al. Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1, 2, 4-triazole Schiff base. RSC Advances. 2019; 9(40): 23045-23052. https://doi.org/10.1039/C9RA05139B

Chaudhary A, Singh A. Schiff bases: An emerging potent class of pharmaceuticals. Int J Curr Res Med Sci 2017; 3(5): 60-74. https://doi.org/10.22192/ijcrms.2017.03.06.009

Govindarao K, Srinivasan N, Suresh R. Synthesis, characterization and antimicrobial evaluation of novel Schiff bases of aryl amines based 2-Azetidinones and 4-thiazolidinones. Office for Official Publications of the European Communities Res J Pharm Technol. 2020; 13(1): 168-172. http://dx.doi.org/10.5958/0974-360X.2020.00034.7

Borrego-Muñoz P, Becerra LD, Ospina F, Coy-Barrera E, Quiroga D. Synthesis (Z) vs (E) selectivity, antifungal activity against Fusarium oxysporum, and structure-based virtual screening of novel Schiff bases derived from L-tryptophan. ACS omega. 2022 Jul 7; 7(28): 24714-24726. https://doi.org/10.1021/acsomega.2c02614

AL-Joubory AK, Abdullah LW, Mohammed AJ. Synthesis, Characterization and Biological Activity Evaluation of Some Pyrazoles, Thiazoles and Oxazoles Derived from 2-Mercaptoaniline. Baghdad Sci J. 2021 Mar 30; 18(1): 764-774. http://dx.doi.org/10.21123/bsj.2021.18.1(Suppl.).0764.

Eftekhari S, Foroughifar N, Hallajian S, Khajeh-Amiri A. Green Synthesis of Some Novel Imidazole Schiff base Derivatives Under Microwave Irradiation/Reflux Conditions and Evaluations of the Antibacterial Activity. Curr. Microw Chem. 2020 Dec 1; 7(3): 207-215. https://doi.org/10.2174/2213335607999200520124245

Mahmoud MA. Synthesis and Characterization of Some New Heterocyclic Compounds Derived from Benzothiazole. In IOP Conference Series: Mat Sci Eng. 2019 Jun 1; 557(1): 1-5. IOP Publishing. https://doi.org/10.1088/1757-899X/557/1/012061

Shukkur A. Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl) methanimine. Baghdad Sci J. 2020 Mar 18; 17(Suppl.): 0272-0286. https://doi.org/10.21123/bsj.2020.17.1(Suppl.).0272.

Djuidje EN, Barbari R, Baldisserotto A, Durini E, Sciabica S, Balzarini J, et al. Benzothiazole derivatives as multifunctional antioxidant agents for skin damage: Structure–activity relationship of a scaffold bearing a five-membered ring system. Antioxidants. 2022 Feb 17; 11(2): 407-1-16. https://doi.org/10.3390/antiox11020407

Geronikaki A, Theophilidis G. Synthesis of 2-(aminoacetylamino) thiazole derivatives and comparison of their local anaesthetic activity by the method of action potential. Eur J Med Chem. 1992 Oct 1; 27(7): 709-716. https://doi.org/10.1016/0223-5234(92)90091-E

Pessoa JC, Correia I. Salan VS. Salen metal complexes in catalysis and medicinal applications: Virtues and pitfalls. Coord Chem Rev. 2019 Jun 1; 388: 227-247. https://doi.org/10.1016/j.ccr.2019.02.035

Ebosie NP, Ogwuegbu MO, Onyedika GO, Onwumere FC. Biological and analytical applications of Schiff base metal complexes derived from salicylidene-4-aminoantipyrine and its derivatives: A review. J Iran Chem Soci. 2021 Dec; 18(12): 3145-3175. https://doi.org/10.1007/s13738-021-02265-1

Nagamine S T, Januszko A, Ohta K, Kaszynski P, Endo Y. A comparison of mesogenic properties of p‐carborane‐1, 12‐dicarbaldehyde schiff bases with their terephthaldehyde analogues. Liq Cryst. 2005 Sep 1; 32(8): 985-995. http://dx.doi.org/10.1080/02678290500291756.

Abdullah MN, Ziwar JB, Musheer NY. Synthesis of some Heterocyclic Compounds (Oxazepine, Diazepine) using Ultrasound Irradiation,''. ZANCO. J Pure Appl Sci. 2016; 28(2): 235-239.

Al-Temimi RB. Preparation, spectral and biological assessment of copper (ii), nickel (ii), zinc (ii), cadmium (ii), vanadium (iv), and zirconium (iv) complexes with azo ligand derived from 4-methoxy-6-methyl-2-H-pyran-2-one. Res J Pharm Tech. 2020; 13(10): 4950-4956. https://doi.org/10.5958/0974-360X.2020.00868.9.

Dalaf AH, Jumaa FH, Yass IA. Synthesis, characterization, biological evaluation, molecular docking, assess laser efficacy, thermal performance and optical stability study for new derivatives of bis-1, 3-oxazepene and 1, 3-diazepine. AIP Conf Proc. 2022 Nov 8; 2394 (1): 1-24. https://doi.org/10.1063/5.0121213.

Hassan SA, Aziz DM, Abdullah MN, Bhat AR, Dongre RS, Ahmed S,et al. Design and synthesis of oxazepine derivatives from sulfonamide Schiff bases as antimicrobial and antioxidant agents with low cytotoxicity and hemolytic prospective. J Mol. Struct. 2023 Nov 15; 1292: 136121. https://doi.org/10.1016/j.molstruc.2023.136121.

Aftan MM, Jabbar MQ, Dalaf AH, Salih HK. Application of biological activity of oxazepine and 2-azetidinone compounds and study of their liquid crystalline behavior. Mater Today: Proceedings. 2021 Jan 1; 43: 2040-2050. https://doi.org/10.1016/j.matpr.2020.11.838

Hou Y, Guo Y, Qian S, Khan H, Han G, Zhang W. A new thermoresponsive polymer of poly (N-acetoxylethyl acrylamide). Polymer. 2019 Mar 22; 167: 159-166. https://doi.org/10.1016/j.polymer.2019.02.008

Alzahrani A, Mirallai SI, Chalmers BA, McArdle P, Aldabbagh F. Synthesis of N-[(dialkylamino) methyl] acrylamides and N-[(dialkylamino) methyl] methacrylamides from Schiff base salts: useful building blocks for smart polymers. Org Biomol Chem. 2018; 16(22): 4108-4016. https://doi.org/10.1039/C8OB00811F.

Alsahib SA, Baqer SR. Synthesis, identification of some new derivatives of 4-amino antipyrine bearing six and seven membered rings. J Phys: Conf Ser. 2021 Mar 1; 1853(1): 1-12.https://doi.org/10.1088/1742-6596/1853/1/012010.

Al-Juburi RM. Synthesis and characterization of some heterocyclic compounds (oxazepine, tetrazole) derived from Schiff bases. Al-Nahrain J Sci. 2012; 15(4): 60-67.

Hussein NN, Muslim AH. Detection of the antibacterial activity of AgNPs biosynthesized by Pseudomonas aeruginosa. Iraqi J Agric Sci. 2019; 50(2): 617-625.

Ibrahim OM, Abed AM, Yahea NZ. Evaluation of Biological Activity of Greenly Synthesized Silver Nanoparticles Using Aloe Vera Gel Extract As Antibacterial Agent In-Vitro and In-Vivo. Iraqi J Agric Sci. 2020; 51(6): 1706-1715.

Silverstein RM, Bassler GC. Spectrometric identification of organic compounds. J Chem Edu.. 1962 Nov; 39(11): 546. https://doi.org/10.1021/ed039p546

Downloads

Issue

Section

article

How to Cite

1.
Synthesis and Characterization of New Acrylamide Derivatives and Studying Their Antibacterial Activity. Baghdad Sci.J [Internet]. [cited 2024 Dec. 21];22(3). Available from: https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/8556