Synthesis and Biological Studies of 4‐Methyl-7‐Ethylcoumarin Derivatives Containing Azo Group
DOI:
https://doi.org/10.21123/bsj.2023.9143Keywords:
Amino coumarin, Anti-microbial activity, Azo dyes, coumarin, Diazonium saltAbstract
New 4-methyl-7-ethylcoumarin derivatives bearing the azo group were synthesized through series of sequential reactions and tested for their biological activity. Starting from 4-methyl-7-ethylcoumarin prepared from a reaction of m-ethyl phenol and ethyl acetoacetate by pechmann condensation reaction, nitration of 4 -methyl-7-ethyl coumarin using nitric acid was carried out in the presence of sulfuric acid to produce one isomer from 4-methyl-7-ethyl-8-nitrocoumarin under the cold condition at (2-5Cº). Then reducing nitro group used iron metal in an acidic medium to form corresponding amino coumarin, which was converted to azo dyes by reacting its diazonium salt with different phenol derivatives. Mass, FT-IR, 1H-NMR, 13C-NMR, UV spectra, and TLC chromatography signposted the preparation compounds. The synthetic compounds' biological activities were evaluated against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) at 1×10-3M. It was found that compounds 4 and 6 have a broad spectrum against different types of bacteria, Staphylococcus aureus, and Escherichia coli, compared to the standard drug vancomycin. In contrast, all compounds showed moderate activity against fungi compared with nystatin. The newly synthesized compounds also showed powerful antioxidants compared with ascorbic acid as a standard, especially compound 7 , which showed high effectiveness as an antioxidant compared to the same reference Ascorbic Acid.
Received 28/05/2023
Revised 08/09/2023
Accepted 10/09/2023
Published Online First 25/12/2023
References
Lončarić M, Gašo-Sokač D, Jokić S, Molnar M. Recent advances in the synthesis of coumarin derivatives from different starting materials. Biomol. 2020; 10(1): 151-186. https://doi.org/10.3390/biom10010151
Pavela R, Maggi F, Benelli G. Coumarin (2H-1-benzopyran-2-one): a novel and eco-friendly aphicide. Nat Prod Res. 2021; 35(9): 1566-1571. https://doi.org/10.3390/app13116535
Zang Y. Pharmacological activities of coumarin compounds in licorice: a review. Nat Prod Commun. 2020; 15(9): 1-17. https://doi.org/10.1177/1934578X20953954
Hadaček F, Müller C, Werner A, Greger H, Proksch P. Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives from Peucedanum (Apiaceae: Apioideae). J Chem Ecol. 1994; 20(8): 2035-2054. https://doi.org/10.3390/molecules23051222
Gao L, Wang F, Chen Y, Li F, Han B, Liu D. The antithrombotic activity of natural and synthetic coumarins. Fitoterapia. 2021; 154: 104947-104964. https://doi.org/10.1016/j.fitote.2021.104947.
Jain P, Joshi H. Coumarin: Chemical and pharmacological profile. J Appl Pharm Sci. 2012; 2: 236-240. https://doi.org/10.3390/cancers12071959.
Omeonu FC, Jonathan SG, Salami AT, Laba SA, Azuh VO. Phytochemical Analysis and In-vitro Antioxidant Activities of Some Selected Higher Fungi from Oyo State, South West of Nigeria. Microbiol Res J Int. 2022; 32(5): 32-41. http://doi.org/10.9734/mrji/2022/v32i530389.
Lončar M, Jakovljević M, Šubarić D, Pavlić M, Buzjak Služek V, Cindrić I, et al. Coumarins in Food and Methods of Their Determination. Foods. 2020; 9(5): 645. https://doi.org/10.3390/foods9050645.
Karakaya S, Bingol Z, Koca M, Dagoglu S, Pınar NM, Demirci B, et al. Identification of non-alkaloid natural compounds of Angelica purpurascens (Avé-Lall.) Gilli. (Apiaceae) with cholinesterase and carbonic anhydrase inhibition potential. Saudi Pharm J. 2020; 28(1): 1-14. http://dx.doi.org/10.1016/j.jsps.2019.11.001.
Rastija V, Vrandečić K, Ćosić J, Kanižai ŠG, Majić I, Karnaš M. Prospects of Computer-Aided Molecular Design of Coumarins as Ecotoxicologically Safe Plant Protection Agents. Appl Sci. 2023; 13: 6535. https://doi.org/10.3390/app13116535
Shu P, Li J, Fei Y, Zhu H , Yu M, Liu A.et al. Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots. J Nat Med. 2020; 74: 456-462. https://doi.org/ 10.1007/s11418-019-01375-8.
Stéphanie H ,Gilbert K. A rapid Access to Coumarin Derivatives (Using Vilsmeier—Haack and Suzuki Cross-Coupling Reactions). Tetrahedron Lett. 2002; 43(7): 1213-1215. https://doi.org/10.1016/S0040-4039(01)02373-5
Oviedo-Sarmiento JS, Cortes JJB, Ávila WAD, Cuca Suárez LE, Daza EH, Patiño-Ladino OJ, et al. Fumigant toxicity and biochemical effects of selected essential oils toward the red flour beetle, Tribolium castaneum (Coleoptera: Tenebrionidae). Pestic Biochem Physiol. 2021; 179: 104941. http://doi.org/10.1016/j.pestbp.2021.104941.
Phadtare SB, Shankarling GS. Greener coumarin synthesis by Knoevenagel condensation using biodegradable choline chloride. Environ Chem Lett. 2012; 10: 363–368.http://doi.org/10.3390/biom10010151
Adimule VM, Nandi SS, Kerur SS, Khadapure SA, Chinnam S. Recent advances in the one-pot synthesis of coumarin derivatives from different starting materials using nanoparticles: A review. Top Catal. Published online 2022: 1-31. https://doi.org/10.1016/j.saa.2023.123210
Zeydi MM, Kalantarian SJ, Kazeminejad Z. Overview on developed synthesis procedures of coumarin heterocycles. J Iran Chem Soc .2020; 17: 3031–3094.https://doi.org/10.1016/j.saa.2023.123210
Wen Z, Yang K, Deng J, Chen L. Advancements in the Preparation of 4H‐Chromenes: An Overview. Adv Synth Catal. 2023; 365(9): 1290-1331. https://doi.org/10.1002/adsc.202201409
Nagaraja O, Bodke YD, Pushpavathi I, Ravi KS. Synthesis, characterization and biological investigations of potentially bioactive heterocyclic compounds containing 4-hydroxy coumarin. Heliyon. 2020; 6(6): e04245. https://doi.org/10.1016/j.heliyon.2020.e04245
Maliyappa MR, Keshavayya J, Mahanthappa M, Shivaraj Y, Basavarajappa K V. 6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: synthesis, characterization, electrochemical and DFT studies. J Mol Struct. 2020; 1199: 126959.https://doi.org/10.1016/j.molstruc.2019.126959
Abdullah AF, Kadhim MM, Naser AW, WITHDRAWN: Novel azo compounds syntheses from sodium saccharin salt: Characterization and DFT studies. Mater Today: Proceedings. 2021. https://doi.org/10.1016/j.matpr.2021.04.522
Jha P, Modi N, Jobby R, Desai N. Differential Expression of Antioxidant Enzymes During Degradation of Azo Dye Reactive black 8 in Hairy roots of Physalis minima L. Int J Phytoremediation. 2015; 17(1-6): 305-312. https://doi.org/10.1080/15226514.2013.876963
Nuruki Y, Matsumoto H, Tsukada M, Tsukahara H, Takajo T, Tsuchida K, et al. Method to Improve Azo-Compound (AAPH)-Induced Hemolysis of Erythrocytes for Assessing Antioxidant Activity of Lipophilic Compounds. Chem Pharm Bull (Tokyo). 2021; 69(1): 67-71. https://doi.org/10.1248/cpb.c20-00568
Sezgin B, Tilki T, Karabacak A Ç, Dede B. Comparative in vitro and DFT antioxidant studies of phenolic group substituted pyridine-based azo derivatives. J Biomol Struct Dyn. 2022; 40(11): 4921-4932. https://doi.org/10.1080/07391102.2020.1863264
Samad MK, Hawaiz FE. Synthesis, characterization, antioxidant power and acute toxicity of some new azo-benzamide and azo-imidazolone derivatives with in vivo and in vitro antimicrobial evaluation. Bioorg Chem. 2019 Apr; 85: 431-444. https://doi.org/10.1016/j.bioorg.2019.01.014
Nagasundaram N, Govindhan C, Sumitha S, Nagarajan S, Krishnan R. Sigamani S. et al. Synthesis, characterization and biological evaluation of novel azo fused 2, 3-dihydro-1H-perimidine derivatives: In vitro antibacterial, antibiofilm, anti-quorum sensing, DFT, in silico ADME and Molecular docking studies. J Mol Struct. 2022; 1248: 131437. https://doi.org/10.1016/j.molstruc.2021.131437
Di Martino M, Sessa L, Di Matteo M, Panunzi B, Piotto S, Concilio S. Azobenzene as Antimicrobial Molecules. Molecules. 2022 Sep 1; 27(17): 5643. https://doi.org/10.3390/molecules27175643
Kyei SK, Akaranta O, Darko G. Synthesis, characterization and antimicrobial activity of peanut skin extract-azo-compounds, Sci Afr. 2020; 8: e00406.https://doi.org/10.1016/j.sciaf.2020.e00406
Banaszak-Leonard E, Fayeulle A, Franche A, Sagadevan S , Billamboz M . Antimicrobial azo molecules: a review. J Iran Chem Soc. 2021; 18: 2829-2851. https://doi.org/10.3390/molecules27186060
Nagasundaram N, Govindhan C, Sumitha S, Nagarajan S, Krishnan R. Sigamani S. et al. Synthesis and anticancer activity of new azo compounds containing extended π-conjugated systems. Chem Pap. 2017; 71: 1463–1469. http://doi.org/10.1007/s11696-017-0140-9
Tahir T, Shahzad MI, Tabassum R, Rafiq M, Ashfaq M, Hassan M et al. Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies. J Enzyme Inhib Med Chem. 2021; 36(1): 1509-1520.https://doi.org/10.1080/14756366.2021.1929949
Maliyappa MR, Keshavayya J. Cu (II), Co (II), Ni (II), Zn (II) and Cd (II) complexes of novel azo ligand 6-hydroxy-4 methyl-2 oxo-5-[(4, 5, 6, 7-tetrahydro-1, 3-benzothiazol-2-yl) diazenyl]-1, 2-dihydropyridine 3-carbonitrile as potential biological agents: synthesis and spectroscop. Chem Pap. 2022; 76(6): 3485-3498. http://doi.org/10.1007/s11696-022-02101-7
Rabbani MAD, Khalili B, Saeidian H. Novel edaravone-based azo dyes: efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra. RSC Adv. 2020; 10(59): 35729-35739. https://doi.org/10.1039/D0RA06934E
Zeebaree SYS, Zeebaree AYS, Zebari OIH. Diagnosis of the multiple effect of selenium nanoparticles decorated by Asteriscus graveolens components in inhibiting HepG2 cell proliferation. Sustain Chem Pharm. 2020; 15: 100210. https://doi.org/10.1016/j.scp.2019.100210
Maliyappa M, Keshavayya J, Mallikarjuna N, Pushpavathi I. Novel substituted aniline based heterocyclic dispersed azo dyes coupling with 5-methyl-2-(6-methyl-1, 3-benzothiazol-2-yl)-2, 4-dihydro-3H-pyrazol-3-one: synthesis, structural, computational and biological studies. J Mol Struct. 2020; 1205: 127576. https://doi.org/10.1016/j.molstruc.2019.127576
Bisht B, Imandi V, Pant S, Sen A. Solvent-dependent spectral properties in diverse solvents, light harvesting and antiviral properties of Mono-azo Dye (Direct Yellow-27): A combined experimental and theoretical study. J Comput Biophys Chem. 2021; 20(06): 619-630.https://doi.org/10.1142/S2737416521500368
Abbas GJ, Mosaa Z, Radhi AJ, Abbas HK, Najem WM. Synthesis, studying analytical properties and biological activity of new transition metal complexes with sulfadiazine derivative as reagent. Egypt J Chem. 2023; 66(1): 55-61. http://doi.org/10.21608/EJCHEM.2022.104212.4814
Mallikarjuna NM, Keshavayya J. Synthesis, spectroscopic characterization and pharmacological studies on novel sulfamethaxazole based azo dyes. J King Saud Univ. 2020; 32(1): 251-259. https://doi.org/10.1016/j.jksus.2018.04.033
Ravi BN, Keshavayya J, Mallikarjuna NM, Santhosh HM. Synthesis, characterization, cyclic voltammetric and cytotoxic studies of azo dyes containing thiazole moiety. Chem Data Collect. 2020; 25: 100334. https://doi.org/10.1016/j.cdc.2019.100334
Ahamed LS. Synthesis of new five-membered hetrocyclic compounds from 2-furfuryl mercaptan derivative and evaluation of their biological activity
J. Glob. Pharma Technol. 2019; 10 (11): 298-304 http://www.jgpt.co.in/index.php/jgpt/article/view/1795
Aly AA, Sayed SM, Abdelhafez ESMN, Naguib SM, Abdelzaher WY, Raslan MA. et al. New quinoline-2-one/pyrazole derivatives; design, synthesis, molecular docking, anti-apoptotic evaluation, and caspase-3 inhibition assay. Bioorg Chem. 2020; 94: 103348. https://doi.org/10.1016/j.bioorg.2019.103348
Sahib HA, Hadi MK, Abdulkadir MQ. Synthesis, and Antimicrobial Evaluation of New hydrazone Derivatives of (2, 4-dinitrophenyl) hydrazine. Res J Pharm Technol. 2022; 15(4): 1743-1748. https://doi.org/10.1016/j.bmc.2014.07.022
Zhou D, Zhuang Y, Sheng Z. Study on effective synthesis of 7-hydroxy-4-substituted coumarins. Heterocycl. Commun. 2022; 28(1): 181-187.https://doi.org/10.1515/hc-2022-0154
Sahoo SS, Shukla S, Nandy S, Sahoo HB. Synthesis of novel coumarin derivatives and its biological evaluations Euro J Exp Bio. 2012; 2 (4): 899-908.https://doi.org/10.1016/j.ejmech.2021.113739
Nofal ZM, El-Zahar MI, Abd El-Karim SS. Novel Coumarin Derivatives with Expected Biological Activity. Molecules. 2000; 5(2): 99-113. https://doi.org/10.3390/50200099
Yazdanbakhsh R, Ghanadzadeh A, Moradi E. Synthesis of some new azo dyes derived from 4-hydroxy coumarin and spectrometric determination of their acidic dissociation constants, J Mol Liq. 2007; 136(1–2): 165-168. https://doi.org/10.1016/j.molliq.2007.03.005
Alsahib SA. Characterization and Biological Activity of Some New Derivatives Derived from Sulfamethoxazole Compound. Baghdad Sci J. 2020; 17(2): 471-480. https://doi.org/10.21123/bsj.2020.17.2.0471
Maged AS, Ahamed LS. Synthesis of new heterocyclic derivatives from 2-furyl methanethiol and study their applications. Eurasian Chem Commun. 2021; 3(7): 461-476. https://doi.org/10.22034/ecc.2021.279489.1158
Fenjan AM, Mahdi IS. Synthesis and Characterization of New Mannich Bases Derived from 7-hydroxy-4-methyl Coumarin. Baghdad Sci J. 2016; 13(2): 235-243.https://doi.org/10.21123/bsj.2016.13.2.2NCC.0235
Fzaa WT. Gamma Ray Effect on the Properties of Coumarin C47 Laser Dye. Baghdad Sci J. 2018; 15(3): 310-313. https://doi.org/10.21123/bsj.2018.15.3.0310
lsahib SA, Dhedan RM. Synthesis and Characterization of some Tetrazole Derivatives and Evaluation of their Biological Activity. E J Chem. 2021; 64(6): 2925-2936.https://doi.org/10.21608/EJCHEM.2021.54356.3165
Alkalidi RAA, Al-Tamimi EO, Al-Shammaree SA. Synthesis and Identification of New 2-Substituted-1, 3, 4- Oxadiazole Compounds from Creatinine and Study Their Antioxidant Activities. J Med Chem Sci. 2023; 6(6): 1216-1229. https://doi.org/10.26655/JMCHEMSCI.2023.6.2
Al-Jeilawi OHR, Oleiwi AQ. Preparation, characterization, antioxidant activity of 1-(2-furoyl) thiourea derivatives and study the molecular docking of them as potent inhibitors of Urease enzyme. Baghdad Sci J. 2023; 20(3): 994-1011. https://doi.org/10.21123/bsj.2023.7745
Downloads
Issue
Section
License
Copyright (c) 2023 Baghdad Science Journal
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
