Email this article 
Novel synthesis of 3-(Phenyl) (ethylamino) methyl)-4-hydroxy-2H-chromen-2-one derivatives using biogenic ZnO nanoparticles and their applications
Abstract
The present work describes the novel synthesis of 3, 3'-((phenyl) (ethylamino) methyl)-4-hydroxy-2H-chromen-2-one derivatives catalyzed by biogenic ZnO nanoparticles. The synthesized heterocyclic compounds were characterized by fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) andmass spectrometric techniques. Absorption, distribution, metabolism and excretion properties and various toxicities (ADMET) studies and in silico molecular docking studies were carried out for the synthesized compounds. The synthesized compounds were screened for their efficacy towards the antioxidant activity and were subjected to corrosion inhibition study towards the mild steel in acidic medium by weight loss method. Additionally, the recyclability of the employed catalyst was studied.
Keywords
Full Text:
PDFReferences
Brahmachari G. Room temperature one-pot green synthesis of coumarin-3- carboxylic acids in water: a practical method for the large-scale synthesis. ACS Sustain Chem Eng. 2015;3:2350−2358. doi:10.1021/acssuschemeng.5b00826
Insuasty D, Castillo J, Becerra D, Rojas H, Abonia R. Synthesis of Biologically Active Molecules through Multicomponent Reac-tions. Mol. 2020;25:505. doi:10.3390/molecules25030505
Slobbe P, Ruijter E. Orru RVA. Recent applications of multi-component reactions in medicinal chemistry. Med Chem Comm. 2012;3:1189. doi:10.1039/c2md20089a
Rao P, Konda S, Iqubal J, Oruganti S. InCl3 catalyzed three-component synthesis of a-benzylamino coumarins and diketones. Tetrahedron Lett. 2012;53:5314–5317. doi:10.1016/j.tetlet.2012.07.098
Kumar A, Kumar Gupta M, Kumar M. An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel ben-zylamino coumarin derivative via Mannich type reaction in aqueous media. Tetrahedron Lett. 2011;52:4521–4525. doi:10.1016/j.tetlet.2011.06.040
Alinasab Amiri A, Javanshir S, Dolatkhah Z, Dekamin MG. SO3H-Functionalized Mesoporous Silica Materials as Solid Acid Catalyst for Facile and Solvent-free Synthesis of 2H-Indazolo [2, 1-b] phthalazine-1, 6, 11-trione derivatives. New J Chem. 2015;39:9665–9671. doi:10.1039/C5NJ01733E
El-Helw EAE, Sallam HA, Elgubbi AS. Antioxidant activity of some N-heterocycles derived from 2-(1-(2-oxo-2H-chromen-3- yl) ethylidene) hydrazinecarbothioamide. Synth Comm. 2019;49(20):2651–2661. doi:10.1080/00397911.2019.1638938
Chen C-M, Chen W-L, Yang S-T, Lin T-H, Yang S-M, et.al. New Synthetic 3-Benzoyl-5-Hydroxy-2H-Chromen-2-One (LM-031) inhibits polyglutamine aggregation and promotes neurite out-growth through enhancement of CREB, NRF2, and Reduction of AMPKα in SCA17 cell models. Oxid Med Cell Longev. 2020;3129497. doi:10.1155/2020/3129497
Qin H-L, Zhang Z-W, Ravindar L, Rakesh KP. Antibacterial activities with the structure-activity relationship of coumarin derivatives. Eur J Med Chem. 2020;207:112832. doi:10.1016/j.ejmech.2020.112832
Hosseinzadegan S, Hazeri N, Maghsoodlou MT. Synthesis and evaluation of antimicrobial and antioxidant activity of novel 7-Aryl-6H, 7H- benzo[f] chromeno [4, 3-b] chromen-6-one by MgO nanoparticle as green catalyst. J Heterocycl Chem. 2019;1–6. doi:10.1002/jhet.3796
Khdhiri E, Mnafgui K, Ncir M, Feriani A, Ghazouani L, et.al. Cardiopreventive capacity of a novel (E)‐Nʹ‐(1‐(7‐methoxy‐ 2‐oxo‐2H‐chromen‐3‐yl) ethylidene)‐4‐methylbenzenesulf ono-hydrazide against isoproterenol‐induced myocardial infarction by moderating biochemical, oxidative stress, and histological parameters. J Biochem Mol Toxicol. 2021;22747. doi:10.1002/jbt.22747
Ali A, Ali A, Bakht MA, Ahsan MJ. Ultrasound promoted synthe-sis of N-(substituted phenyl)-2-(7– hydroxy-4-methyl-2H-chromen-2-ylidene) hydrazine-1-carboxamides as cytotoxic and antioxidant agents. J Mol Struct. 2021;1238:130452. doi:10.1016/j.molstruc.2021.130452
Bensalah D, Mnasri A, Chakchouk-Mtibaa A, Mansour L, Mellouli L, Hamdi N. Synthesis and antioxidant properties of some new thiazolyl coumarin derivatives. Green Chem Lett Rev. 2020;13(2):155–163. doi:10.1080/17518253.2020.1762935
Alshib HM, Al-Abdullah ES, Haiba ME, Alkahtani HM, Awad GEA, et al. Synthesis and evaluation of new coumarin deriva-tives as antioxidant, antimicrobial, and anti-inflammatory agents. Mol. 2020;25:3251. doi:10.3390/molecules25143251
Bansal Y, Sethi P, Bansal G. Coumarin: a potential nucleus for anti-inflammatory molecules. Med Chem Res. 2013;22:3049–3060. doi:10.1007/s00044-012-0321-6
Nagaraja O, Bodke YD, Pushpavathi I, Ravi Kumar S. Synthesis, characterization and biological investigations of potentially bio-active heterocyclic compounds containing 4-hydroxy coumarin. Heliyon. 2020;6:e042452. doi:10.1016/j.heliyon.2020.e04245
Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. A review on recent advances in nitrogen-containing molecules and their biological applications. Mol. 2020;25:1909. doi:10.3390/molecules25081909
Kamal LC, Sethuraman MG. Opuntiol: an active principle of opuntia elatior as an eco-friendly inhibitor of corrosion of mild steel in acid medium. ACS Sustain Chem Eng. 2014;2:606–613. doi:10.1021/sc4003642
Gopal J. Priyanka dwivedi, shanthi sundaram and rajiv pra-kash. Inhibitive effect of chlorophytum borivilianum root ex-tract on mild steel corrosion in HCl and H2SO4 solutions. Ind Eng Chem Res. 2013;52:10673–10681. doi:10.1021/ie4008387
Al-Amiery AA, Al-Majedy YK, Kadhum AAH, Mohamad AB. New coumarin derivative as an eco-friendly inhibitor of corrosion of mild steel in acid medium. Mol. 2015;20:366–383. doi:10.3390/molecules20010366
Singh AK, Shukla SK, Quraishi MA, Ebenso EE. Investigation of adsorption characteristics of N, N-[(methylimino)dimethylidyne] di-2,4-xylidine as corrosion in-hibitor at mild steel/sulphuric acid interface. J Taiwan Inst Chem Eng. 2012;43:463–472. doi:10.1016/j.jtice.2011.10.012
Ghosh PP, Das AR. Nano crystalline ZnO: a competent and re-usable catalyst for one pot synthesis of novel benzylamino coumarin derivatives in aqueous media. Tetrahedron Lett. 2012;53:3140–3143. doi:10.1016/j.tetlet.2012.04.033
Viradiya DJ, Kotadiya VC, Khunt MD, Baria BH, Bhoya UC. PEG mediated eco-friendly one pot synthesis of benzylamine cou-marin derivatives using multicomponent reactant. Int Lett Chem Phys Astron. 2014;11(2):177–184.
Cao B, Liu R, Huang ZX, Ge S. Flash synthesis of flower-like ZnO nanostructures by microwave-induced combustion pro-cess. Mater Lett. 2011;65:160–163. doi:10.1016/j.matlet.2010.09.072
Kumar B, Smita K, Cumbal L, Debut A. Green approach for fabrication and applications of zinc oxide nanoparticles. Bio-inorg Chem Appl. 2014;523869. doi:10.1155/2014/523869
Banerjee B. Recent developments on nano ZnO catalyzed syn-thesis of bioactive heterocycles. J Nanostruct Chem. 2017;7:389–413. doi:10.1007/s40097-017-0247-0
Molinspiration Cheminformatics. Available from: http://www.molinspiration.com/
ADMETlab. Available from: http://admet.scbdd.com/
Shwetha UR, Rajith Kumar CR, Kiran MS, Virupaxappa S. Be-tageri, Latha MS, et. al. Biogenic synthesis of NiO nanoparticles using areca catechu leaf extract and their antidiabetic and cy-totoxic effects. Mol. 2021;26(9):2448. doi:10.3390/molecules26092448
Lipinski CA. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discovery Today: Technol. 2004;1(4):337–341. doi:10.1016/j.ddtec.2004.11.007
Manjunatha KS, Satyanarayan ND, Kaviraj MY, Adarsha HJ. Anti-proliferative and ADMET screening of novel 3-(1H-indol-3-yl)-1, 3-diphenylpropan-1-one derivatives: Cogent Chem. 2016;2(1):1172542. doi:10.1080/23312009.2016.1172542
Shatokhin SS, Tuskaev VA, Gagieva SCh, Ybalkina EYu, et.al. Synthesis, structural characterization, antioxidant and cytotox-ic activity towards human cancer cell lines and computational studies of new Ni(II), Co(II) and Pd(II) complexes with 3-[bis(3,5-dimethylpyrazol-1-yl)methyl]chromen-4-one deriva-tives. J Mol Struct. 2021. doi:10.1016/j.molstruc.2021.130706
Kara J, Suwanhom P, Wattanapiromsakul C, Nualnoi T, Pu-ripattanavong J, et.al. Synthesis of 2‐(2‐oxo‐2H‐chromen‐4‐yl) acetamides as potent acetylcholinesterase inhibitors and mo-lecular insights into binding interactions. Chem Life Sci. 2019;1800310. doi:10.1002/ardp.201800310
Dong J, Wang N-N, Yao Z-J. ADMETlab: a platform for system-atic ADMET evaluation based on a comprehensively collected ADMET database. J Chem. 2018;10. doi:10.1186/s13321-018-0283-x
Rowlinson SW, Kiefer JR, Prusakiewicz JJ, Pawlitz JL, Kozak KR, Kalgutkar AS, Stallings WC, Kurumbail RG, Marnett LJ. A Novel mechanism of cyclooxygenase-2 inhibition involving in-teractions with Ser-530 and Tyr-385, J Biol Chem. 2003;278:45763–45769. doi:10.1074/jnc.M305481200
RCSB PDB. Available from: https://www.rcsb.org
Gaillard T. Evaluation of AutoDock and AutoDock Vina on the CASF-2013 Benchmark. J Chem Inf Model. 2018;58:1697−1706. doi:10.1021/acs.jcim.8b00312
Bhowmik D, Sharma RD, Prakash A, Kumar D. Identification of nafamostat and VR23 as COVID-19 drug candidates by targeting 3CLpro and PLpro. J Mol Struct. 2021;1233:130094. doi:10.1016/j.molstruc.2021.130094
Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. A visualization system for exploratory research and analysis. J Comput Chem. 2004;25(13):1605–1612. doi:10.1002/jcc.20084
Pradeep P, Archana Y, Laxman B, Nippu BN, Satyanarayan ND, Anand M, Akshay G, Shankar H, Sandeep S. [MerDABCO-SO3H]Cl catalyzed synthesis, antimicrobial and antioxidant evaluation and molecular docking study of pyrazolopyranopy-rimidines. J Mol Struct. 2021;1242:130672. doi:10.1016/j.molstruc.2021.130672
Sahar A, Khan ZA, Ahmad M, Zahoor AF, Mansha A, et.al. Syn-thesis and antioxidant potential of some biscoumarin deriva-tives. Tropical J Pharm Res. 2017;16(1):203–210. doi:10.4314/tjpr.v16i1.27
Nagaraja O, Bodke YD, Kenchappa R, Ravi Kumar S. Synthesis and characterization of 3-[3-(1H-benzimidazol-2-ylsulfanyl)-3-phenyl propanoyl]-2H-chromen-2-one derivatives as potential biological agents. Chem Data Collect. 2020;27:100369. doi:10.1016/j.cdc.2020.100369
Yasar Q, Zahee Z. 4-aminoantipyrine analogs as anti-inflammatory and antioxidant agents: synthesis, biological evaluation and molecular docking studies. Int J Pharm Investig. 2021;11(1):14–22. doi:10.5530/ijpi.2021.1.4
Al-Azawi KF, Al-Baghdadi SB, Mohamed AZ, Al-Amiery AA, Abed TK, Mohammed SA, et. al. Synthesis, inhibition effects and quantum chemical studies of a novel coumarin derivative on the corrosion of mild steel in a hydrochloric acid solution. Chem Cent J. 2016;10:23. doi:10.1186/s13065-016-0170-3
Abdallah M, Zaafarany IA, Foudaand AS, El-Nagar W. Coumarin Derivatives as Corrosion Inhibitors for Zinc in HCl Solutions. J Electrochem Plat Technol. 2014. doi:10.12850/ISSN2196-0267.JEPT3190
Vinutha MR, Venkatesha TV, Nagaraja C. Anticorrosive ability of electrochemically synthesized 2, 2′ disulfanediyldianiline for mild steel corrosion: electrochemical and thermodynamic studies. Int J Ind Chem. 2018;9:185–197. doi:10.1007/s40090-018-0149-0
DOI: https://doi.org/10.15826/chimtech.2022.9.1.04
Copyright (c) 2021 G.C. Anjan Kumar, Yadav D. Bodke, B. Manjunatha, N.D. Satyanarayan, B.N. Nippu, Muthipeedika Nibin Joy
This work is licensed under a Creative Commons Attribution 4.0 International License.
Chimica Techno Acta, 2014-2024
ISSN 2411-1414 (Online)
Copyright Notice