Synthesis and Estimation of the Insecticide and Antibacterial Activities for Some New Amide Derivatives

https://doi.org/10.22146/ijc.81972

Zinah Hussein Ali(1), Dina Saleem(2*), Abbas Khudhair Abbas(3), Baneen Salam Rasool(4), Mustafa Sabri Cheyad(5)

(1) Department of Pharmaceutical Chemistry, College of Pharmacy, Al-Mustansiriyah University, Baghdad 10052, Iraq
(2) Department of Pharmaceutical Chemistry, College of Pharmacy, Al-Mustansiriyah University, Baghdad 10052, Iraq
(3) Muthanna Agriculture Directorate, Ministry of Agriculture, Al-Muthanna 66001, Iraq
(4) College of Science, Al-Nahrain University, Baghdad 10072, Iraq
(5) Oil Products Distribution Company (OPDC), Ministry of Oil, Baghdad 10022, Iraq
(*) Corresponding Author

Abstract


In this work, new compounds of amide derivatives (C1-C3) were synthesized through the conversion reaction of p-chloroaniline to diazonium salt (B1), which reacts with aniline to form a new azo-compound (B3). Synthesized of p-alkoxybenzoic acid (A1-A3) and reacts with SOCl2 to form A4-A6 compounds that react with B3 compound to form amide compounds (C1-C3). The synthesized derivatives were tested by docking analysis and characterized via FTIR, 1H-NMR spectra. In the docking study, the interaction diagram also displays many van der Waals interactions, which are used to estimate the synthetic compounds' activity as insecticides like anti-termites. Heptyl came in first on the binding score, followed by octyl and then nonyl. Due to the compounds' modified conformation in interacting with the enzyme's binding pocket, the length of the alkyl residue of the derivative adversely impacted their binding inhibition. The synthesized compounds (C1 and C3) give a good result as anti-E. coli and anti-Staphylococcus strains.

 


Keywords


amide; azo; insecticide; bacterial



References

[1] Massolo, E., Pirola, M., and Benaglia, M., 2020, Amide bond formation strategies: Latest advances on a dateless transformation, Eur. J. Org. Chem., 2020 (30), 4641–4651.

[2] Adler, P., Gras, M., and Smietana, M., 2023, Catalytic and sustainable amide bond formation using a DABCO/Dichlorotriazine system, ChemCatChem, 15 (20), e202300264.

[3] Haas, B., Goetz, A., Bahamonde, A., McWilliams, J.C., and Sigman, M.S., 2022, Predicting relative efficiency of amide bond formation using multivariate linear regression, Proc. Natl. Acad. Sci. U. S. A., 119 (16), e2118451119.‏

[4] Weiser, L.J., and Santiso, E.E., 2019, A CGenFF‐based force field for simulations of peptoids with both cis and trans peptide bonds, J. Comput. Chem., 40 (22), 1946–1956.‏

[5] Conic, D., Pierloot, K., Parac-Vogt, T.N., and Harvey, J.N., 2020, Mechanism of the highly effective peptide bond hydrolysis by MOF-808 catalyst under biologically relevant conditions, Phys. Chem. Chem. Phys., 22 (43), 25136–25145.

[6] Henninot, A., Collins, J.C., and Nuss, J.M., 2018, The current state of peptide drug discovery: Back to the future, J. Med. Chem., 61 (4), 1382–1414.

[7] Bousfield, T.W., Pearce, K.P.R., Nyamini, S.B., Angelis-Dimakis, A., and Camp, J.E., 2019, Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™, Green Chem., 21 (13), 3675–3681.

[8] Sanz Sharley, D.D., and Williams, J.M.J., 2017, Acetic acid is a catalyst for the N-acylation of amines using esters as the acyl source, Chem. Commun., 53 (12), 2020–2023.

[9] Shankarling, G.S., Deshmukh, P.P., and Joglekar, A.R., 2017, Process intensification in azo dyes, J. Environ. Chem. Eng., 5 (4), 3302–3308.

[10] Gürses, A., Açıkyıldız, M., Güneş, K., and Gürses, M., 2016, “Classification of Dye and Pigments” in Dyes and Pigments, Springer International Publishing, Cham, Switzerland, 31–45.

[11] Shah, M., 2014, Effective treatment systems for azo dye degradation: A joint venture between Physico-chemical & microbiological process, Int. J. Environ. Biorem. Biodegrad., 2 (5), 231–242.

[12] Zhu, Y., and Zhang, S., 2020, Antibacterial activity and mechanism of lacidophilin from Lactobacillus pentosus against Staphylococcus aureus and Escherichia coli, Front. Microbiol., 11, 582349.‏

[13] Cheung, G.Y.C., Bae, J.S., and Otto, M., 2021, Pathogenicity and virulence of Staphylococcus aureus, Virulence, 12 (1), 547–569.‏

[14] Sharma, K., 2019, Cholinesterase inhibitors as Alzheimer's therapeutics (Review), Mol. Med. Rep., 20 (2), 1479–1487.‏

[15] Al-Jamali, N.M., 2013, Synthesis and identification of oxazipen, diazipene compounds via peri cyclic reactions, J. Chem. Chem. Sci., 3 (2), 64–69.

[16] Sivasri, J., Pardhasaradhi, P., Madhav, B.T.P., Tejaswi, M., and Manepalli, R.K.N.R., 2020, Birefringence studies on alkoxy benzoic acids with dispersed Fe3O4 nanoparticles, Liq. Cryst., 47 (32), 330–344.

[17] Gaffer, H.E., 2019, Antimicrobial sulphonamide azo dyes, Color. Technol., 135 (6), 484–500.‏

[18] Hadi, D.M., and Jber, N.R., 2017, Synthesis and spectroscopic characterization of bis-swallow tailed mesogen, Int. J. Sci. Res., 6 (1), 1909–1915.

[19] Eberhardt, J., Santos-Martins, D., Tillack, A.F., and Forli, S., 2021, AutoDock Vina 1.2.0: New docking methods, expanded force field, and Python bindings, J. Chem. Inf. Model., 61 (8), 3891–3898.

[20] Trott, O., and Olson, A.J., 2010, AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31 (2), 455–461.

[21] Ozaki, Y., Huck, C., Tsuchikawa, S., and Engelsen, S.B., 2021, Near-Infrared Spectroscopy: Theory, Spectral Analysis, Instrumentation, and Applications, Springer, Singapore.

[22] Sharma, S.K., Verma, D.S., Khan, L.U., Kumar, S., and Khan, S.B., 2018, Handbook of Materials Characterization, Springer, Cham, Switzerland.

[23] Singh, K.D., Labala, R.K., Devi, T.B., Singh, N.I., Chanu, H.D., Sougrakpam, S., Nameirakpam, B.S., Sahoo, D., and Rajashekar, Y., 2017, Biochemical efficacy, molecular docking and inhibitory effect of 2,3-dimethylmaleic anhydride on insect acetylcholinesterase, Sci. Rep., 7 (22), 12483.



DOI: https://doi.org/10.22146/ijc.81972

Article Metrics

Abstract views : 1265 | views : 638 | views : 292


Copyright (c) 2023 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.