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New spiro-heterocyclic coumarin derivatives as antibacterial agents: design, synthesis and molecular docking

Abdallah F. Al-burgus, Omar T. Ali, Omar Y. Al-abbasy

Abstract


Coumarin derivatives were synthesized herein from 3-acetyl coumarin and 4-(pyrimidin-2-yldiazenyl) antipyrine, leading to the azo chalcone intermediate compound. The final spiro-heterocyclic coumarins were produced through the cyclization of the azo-chalcone with thiourea, guanidine hydrochloride, benzene-1,2-diamine, 2-aminophenol, and hydroxylamine hydrochloride, respectively. The obtained target compounds were purified by column chromatography and characterized by FT-IR, 1H NMR, 13C-NMR and elemental analysis. The antibacterial activity of the synthesized compounds was evaluated in vitro against Gram-negative and Gram-positive bacteria. One of the compounds showed significant antibacterial activity. Furthermore, the docking study of this compound with DNA gyrase for E. coli and S. aureus bacterial strains was investigated, which revealed vital interactions and binding.

Keywords


spiro-cyclic; coumarin derivatives; antibacterial agent; molecule docking

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References


Rodriguez-Enriquez F, Costas- Lago C, Besada P, Alonso-Pena M, Torres-Teran I, Vina D, Teran C. Novel coumarin-pyridazine hybrids as selective MAO-B inhibitors for the Parkinson’s disease therapy. Bioorg Chem. 2020; 104:104203. doi:10.1016/j.bioorg.2020.104203

García-Beltrán O, Mena NP, Aguirre P, Barriga-Gonzalez G, Galdámez A, Nagles E, Núñez MT. Development of an iron-selective antioxidant probe with protective effects on neu-ronal function. J PloS one. 2017;12(12):0189043. doi:10.1371/journal.pone.0189043

Aguirre P, García-Beltrán O, Tapia V, Muñoz Y, Cassels BK, Núñez MT. Neuroprotective effect of a new 7, 8-dihydroxycoumarin-based Fe2+/Cu2+ chelator in cell and an-imal models of Parkinson’s disease. ACS Chem Neurosci. 2017;8(1):178-185. doi:10.1021/acschemneuro.6b00309

Al-Abbasy OY, Younus SA, Rashan AI, Ahmad OA. Maillard reaction: formation, advantage, disadvantage and control. A review. Food Sci Appl Biotech. 2024;7(1):145–161. doi:10.30721/fsab2024.v7. i1.333

Shen YF, Liu L, Feng CZ, Hu Y, Chen C, Wang GX, Zhu B. Synthesis and antiviral activity of a new coumarin deriva-tive against spring viremia of carp virus. Fish Shellfish Im-munol. 2018; 81:57-66. doi:10.1016/j.fsi.2018.07.005

Sahoo CR, Paidesetty SK, Sarathbabu S, Dehury B, Senthil Kumar N, Padhy RN. Molecular dynamics simulation, syn-thesis and topoisomerase inhibitory actions of vanillin de-rivatives: a systematic computational structural integu-ment. J Biomol Struct Dyn. 2022;40(22):11653-11663. doi:10.1080/07391102.2021.1961867

Cione E, La Torre C, Cannataro R, Caroleo MC, Plastina P, Gallelli L. Quercetin, epigallocatechin gallate, curcumin, and resveratrol: from dietary sources to human microRNA modulation. Molecules. 2019;25(1):63. doi:10.3390/molecules25010063

Ali OT, Mohammed MO, Al Dulayymi JR, Baird MS. Synthe-sis of a di-mycoloyl tri-arabinofuranosyl glycerol fragment of the mycobacterial cell wall, based on synthetic mycolic acids. Molecules. 2019;24(19):3596. doi:10.3390/molecules24193596

Galvin CJ, Hobson M, Meng JX, Ierokomos A, Ivanov IE, Ber-ger JM, Bryant Z. Single-molecule dynamics of DNA gyrase in evolutionarily distant bacteria Mycobacterium tuberculo-sis and Escherichia coli. Bio chem; 2023: 299(5). doi:10.1016/j.jbc.2023.103003

Khan T, Sankhe K, Suvarna V, Sherje A, Patel K, Dravyakar BDN. A gyrase inhibitors: Progress and synthesis of potent compounds as antibacterial agents. Biomed Pharmacother; 2018; 103: 923-938‏. doi:10.1016/j.biopha.2018.04.021

Maxwell A. DNA gyrase as a drug target. Trends Microbiol. 1997; 5:102–109. doi:10.1016/S0966-842X(96)10085-8

Rashan AI, Altaee RT, Salh FS, AL-Abbasy OY, Al-Lehebe N. The role of polyamines in plants: A review. Plant Sci Today. 2023; 10:164–171. doi:10.14719/pst.2520

Patil SA, Unki SN, Kulkarni AD, Naik VH, Badami PS. Co (II), Ni (II) and Cu (II) complexes with coumarin-8-yl Schiff-bases: spectroscopic, in vitro antimicrobial, DNA cleavage and fluorescence studies. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79(5):1128-1136.‏ doi:10.1016/j.saa.2011.04.032

Abdelmohsen SA, El-Emary T. Synthesis, characterization and antimicrobial activity of novel pyrazolo [3, 4-b] pyri-dines and their spiro-hetero cyclic derivatives. J Adv Chem. 2014;10(7).‏ doi:10.24297/jac. v10i7.6802

Patagar D, Uttarkar A, Patra SM, Patil JH, Kusanur R, Niran-jan V, Kumar HA. Spiro benzodiazepine substituted fluo-rocoumarins as potent anti-anxiety agents. Russ J Bioorg Chem. 2021;47(2):390-398. doi:10.1134/S1068162021020199

Abd Allah OA, Elkhayat ES, Moustafa AH, Fahmy AA. Synthe-sis and Characterization of Some Novel Indole-2-One-Coumarin Hybrids. Sohag J Sci. 2024;9(2):186-189. doi:10.21608/sjsci.2024.248555.1148

‏Özer H, Sökmen M, Güllüce M, Adigüzel A, Şahin F, Sökmen A, Bariş Ö. Chemical composition and antimicrobial and an-tioxidant activities of the essential oil and methanol extract of Hippomarathrum microcarpum (Bieb.) from Turkey. J Agric Food. 2007;55(3):937-942.‏ doi:10.1021/jf0624244

Vashistha VK, Mittal A, Bala R, DASa DK, Singh PP. Synthe-sis, characterization, electrochemical and antibacterial studies of mn4-type macrocyclic complexes of Ni (II). Rev Roum Chim. 2023;68(9):447-452. doi:10.33224/rrch.2023.68.9.05

Almaghrabi M, Musa A, Aljohani AK, Ahmed HE, Alsulaim-any M, Miski SF, El-Agrody AM. Introducing of novel class of pyrano [2, 3-c] pyrazole-5-carbonitrile analogs with potent antimicrobial activity, DNA gyrase inhibition, and promi-nent pharmacokinetic and CNS toxicity profiles supported by molecular dynamic simulation. ACS Omega. 2023;8(20):17948–17965. doi:10.1080/07391102.2023.2252088

Rodriguez SV, Guíñez RF, Matos MJ, Azar CO, Maya JD, San-tana L, Borges F. Synthesis and trypanocidal properties of new coumarin-chalcone derivatives. Med Chem. 2015;(5):173-177.‏ doi:10.4172/2161-0444.1000260

Ahmed EY, Abdelhafez OM, Zaafar D, Serry AM, Ahmed YH, El‐Telbany RFA, Ali HI. Antitumor and multikinase inhibi-tion activities of some synthesized coumarin and benzofu-ran derivatives. Archiv der Pharmazie. 2022;355(6):2100327. doi:10.1002/ardp.202100327

Dar PA, Bhat BA, Mir MA, Chaudhari SY, Shah WA. Synthe-sis, biological profile and computational insights of new de-rivatives of benzo [B][1, 4] diazepines as prospective anti-cancer agents for inhibiting the CDK-2 protein. J Biomol Struct Dyn. 2024:1-16.‏ doi:10.1080/07391102.2024.2314270

Solankee A, Tailor R. Synthesis, characterization and biolog-ical screening of s-triazine based chalcones and its derivati-zation into phenyl pyrazolines, isoxazoles. Int Lett Chem Phys Astron. 2015; 47:109-119. doi:10.56431/p-jy3j82




DOI: https://doi.org/10.15826/chimtech.2024.11.3.08

Copyright (c) 2024 Abdallah F. Al-burgus, Omar T. Ali, Omar Y. Al-abbasy

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