Synthesis, antibacterial and computational studies of Halo Chalcone hybrids from 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one

Journal of the Indian Chemical Society - Tập 98 - Trang 100051 - 2021
Rahul A. Shinde1, Vishnu A. Adole1, Bapu S. Jagdale1, Bhatu S. Desale1
1PG Department of Chemistry, Mahatma Gandhi Vidyamandir's Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune) Manmad, Maharashtra, India

Tài liệu tham khảo

Yin, 2019, Design, synthesis and biological evaluation of chalcones as reversers of P-glycoprotein-mediated multidrug resistance, Eur. J. Med. Chem., 180, 350, 10.1016/j.ejmech.2019.05.053 da Cunha Xavier, 2021, Structural characterization, DFT calculations, ADMET studies, antibiotic potentiating activity, evaluation of efflux pump inhibition and molecular docking of chalcone (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl) prop-2-en-1-one, J. Mol. Struct., 1227, 129692, 10.1016/j.molstruc.2020.129692 Božić, 2014, Antibacterial activity of three newly-synthesized chalcones & synergism with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus, Indian J. Med. Res., 140, 130 Rammohan, 2020, Chalcone synthesis, properties and medicinal applications: a review, Environ. Chem. Lett., 18, 433, 10.1007/s10311-019-00959-w Gaonkar, 2017, Synthesis and pharmacological properties of chalcones: a review, Res. Chem. Intermed., 43, 6043, 10.1007/s11164-017-2977-5 K Sahu, 2012, Exploring pharmacological significance of chalcone scaffold: a review, Curr. Med. Chem., 19, 209, 10.2174/092986712803414132 Riaz, 2019, Synthesis and evaluation of novel α-substituted chalcones with potent anti-cancer activities and ability to overcome multidrug resistance, Bioorg. Chem., 87, 123, 10.1016/j.bioorg.2019.03.014 Burmaoglu, 2017, Design of potent fluoro-substituted chalcones as antimicrobial agents, J. Enzym. Inhib. Med. Chem., 32, 490, 10.1080/14756366.2016.1265517 Mathew, 2017, Anti-oxidant behavior of functionalized chalcone-a combined quantum chemical and crystallographic structural investigation, J. Mol. Struct., 1146, 301, 10.1016/j.molstruc.2017.05.100 Bhale, 2017, Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents, Bioorg. Med. Chem. Lett, 27, 1502, 10.1016/j.bmcl.2017.02.052 Anandam, 2018, Synthesis of new C-dimethylated chalcones as potent antitubercular agents, Med. Chem. Res., 27, 1690, 10.1007/s00044-018-2183-z Mirossay, 2018, Antiangiogenic effect of flavonoids and chalcones: an update, Int. J. Mol. Sci., 19, 27, 10.3390/ijms19010027 Lee, 2021, Antibreast cancer activity of aspirin-conjugated chalcone polymeric micelles, Macromol. Res., 29, 105, 10.1007/s13233-021-9010-y Mt Albuquerque, 2014, Chalcones as versatile synthons for the synthesis of 5-and 6-membered nitrogen heterocycles, Curr. Org. Chem., 18, 2750, 10.2174/1385272819666141013224253 Nair, 2016, Regioselective synthesis of pyrazole and pyridazine esters from chalcones and α-diazo-β-ketoesters, Tetrahedron Lett., 57, 3146, 10.1016/j.tetlet.2016.06.020 Wang, 2017, Synthesis, cytotoxic activity and drug combination study of tertiary amine derivatives of 2′,4′-dihydroxyl-6′-methoxyl-3′,5′-dimethylchalcone, RSC Adv., 7, 48031, 10.1039/C7RA08639C Goyal, 2021, Chalcones: a review on synthesis and pharmacological activities, J. Appl. Pharmaceut. Sci., 11, 1 Gomes, 2017, Chalcone derivatives: promising starting points for drug design, Molecules, 22, 1210, 10.3390/molecules22081210 Asadi, 2017, A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy, J. Mol. Struct., 1128, 552, 10.1016/j.molstruc.2016.09.027 Humphries, 2009, A structural study of bis-(trimethylamine)alane, AlH3·2NMe3, by variable temperature X-ray crystallography and DFT calculations, J. Mol. Struct., 923, 13, 10.1016/j.molstruc.2008.12.022 Raja, 2017, Synthesis, spectroscopic (FT-IR, FT-Raman, NMR, UV–Visible), NLO, NBO, HOMO-LUMO, Fukui function and molecular docking study of (E)-1-(5-bromo-2-hydroxybenzylidene) semicarbazide, J. Mol. Struct., 1141, 284, 10.1016/j.molstruc.2017.03.117 Karthikeyan, 2015, Spectroscopic [FT-IR and FT-Raman] and theoretical [UV–Visible and NMR] analysis on α-Methylstyrene by DFT calculations, Spectrochim. Acta Mol. Biomol. Spectrosc., 143, 107, 10.1016/j.saa.2015.02.015 Dhonnar, 2021, Structural, spectroscopic (UV-vis and IR), electronic and chemical reactivity studies of (3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)(phenyl)methanone, Phys. Chem. Res., 9, 193 Adole, 2020, Solvent-free grindstone synthesis of four new (E)-7-(arylidene)-indanones and their structural, spectroscopic and quantum chemical study: a comprehensive theoretical and experimental exploration, Mol. Simulat., 46, 1045, 10.1080/08927022.2020.1800690 Adole, 2020, Ultrasound promoted stereoselective synthesis of 2,3-dihydrobenzofuran appended chalcones at ambient temperature, S. Afr. J. Chem., 73, 35 Khadri, 2020, Synthesis, structural, thermal, Hirshfeld surface and DFT studies on a new hybrid compound: bis[4-(dimethylamino)pyridinium]tetrachloridomanganate(II), J. Coord. Chem., 73, 609, 10.1080/00958972.2020.1738408 Adole, 2021, DFT computational insights into structural, electronic and spectroscopic parameters of 2-(2-Hydrazineyl)thiazole derivatives: a concise theoretical and experimental approach, J. Sulphur Chem., 42, 131, 10.1080/17415993.2020.1817456 Pathade, 2020, Experimental and computational investigations on the molecular structure, vibrational spectra, electronic properties, FMO and mep analyses of 4,6-Bis(4-Fluorophenyl)-5,6-dihydropyrimidin-2(1H)-one: a DFT insight, Phys. Chem. Res., 8, 671 Sadgir, 2020, Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one, SN Appl. Sci., 2, 1, 10.1007/s42452-020-2923-9 Devi, 2020, One-pot synthesis, spectroscopic characterizations, quantum chemical calculations, docking and cytotoxicity of 1-((dibenzylamino)methyl)pyrrolidine-2,5-dione, J. Mol. Struct., 1203, 127403, 10.1016/j.molstruc.2019.127403 Adole, 2020, Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)-7-(arylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one derivatives: a comparative study, J. Chin. Chem. Soc., 67, 1763, 10.1002/jccs.202000006 Rajamani, 2020, Synthesis, characterization, spectroscopic, DFT and molecular docking studies of 3-(3,4-dihydroxyphenyl)-1-phenyl-3-(Phenylamino)Propan-1-one, Polycycl. Aromat. Comp., 1, 10.1080/10406638.2020.1837190 Mariappan, 2014, FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra, molecular geometry, conformational stability and some molecular properties of 1-Bromo-2,3-dimethoxynaphthalene, J. Mol. Struct., 1074, 51, 10.1016/j.molstruc.2014.04.022 Pradeepa, 2015, Spectroscopic and molecular structure investigations of 9-vinylcarbazole by DFT and ab initio method, Spectrochim. Acta A Mol. Biomol. Spectrosc., 136, 690, 10.1016/j.saa.2014.09.083 Mariappan, 2013, Structural, vibrational, electronic and NMR spectral analysis of benzyl phenyl carbonate, Spectrochim. Acta A Mol. Biomol. Spectrosc., 110, 169, 10.1016/j.saa.2013.03.019 Govindarasu, 2015, Synthesis, structural and spectral analysis of (E)-N′-(4-Methoxybenzylidene) pyridine-3-carbohydrazide dihydrate by density functional theory. Spectrochim, Acta A Mol. Biomol. Spectrosc., 135, 1123, 10.1016/j.saa.2014.08.014 Khan, 2019, Microwave-assisted synthesis, characterization, and density functional theory study of biologically active ferrocenyl bis-pyrazoline and bis-pyrimidine as organometallic macromolecules, J. Heterocycl. Chem., 56, 312, 10.1002/jhet.3381 Pitchumani Violet Mary, 2019, Theoretical insights into the metal chelating and antimicrobial properties of the chalcone based Schiff bases, Mol. Simulat., 45, 636, 10.1080/08927022.2019.1573370 Khan, 2019, Microwave assisted synthesis of chalcone and its polycyclic heterocyclic analogues as promising antibacterial agents: in vitro, in silico and DFT studies, J. Mol. Struct., 1190, 77, 10.1016/j.molstruc.2019.04.046 Rathi, 2020, Quantum parameters based study of some heterocycles using density functional theory method: a comparative theoretical study, J. Chin. Chem. Soc., 67, 213, 10.1002/jccs.201900134 Shinde, 2020, Efficient synthesis, spectroscopic and quantum chemical study of 2,3-dihydrobenzofuran labelled two novel arylidene indanones: a comparative theoretical exploration, Mat. Sci. Res. India, 17, 146, 10.13005/msri/170207 Pearson, 1989, Absolute electronegativity and hardness: applications to organic chemistry, J. Org. Chem., 54, 1423, 10.1021/jo00267a034 Frisch, 2004 Jorgensen, 2015, Susceptibility test methods: dilution and disk diffusion methods, Manual of clinical microbiology, 1253, 10.1128/9781555817381.ch71 Johnson, 2015, Susceptibility test methods: yeasts and filamentous fungi, Manual of Clinical Microbiology, 2255, 10.1128/9781555817381.ch131