Synthesis, experimental, theoretical study and molecular docking of 1-ethylpiperazine-1,4-diium bis(nitrate)

Solid State Sciences - Tập 106 - Trang 106326 - 2020
Sofian Gatfaoui1, Abir Sagaama2, Noureddine Issaoui2, Thierry Roisnel3, Houda Marouani1
1Université de Carthage, Faculté des Sciences de Bizerte, LR13ES08 Laboratoire de Chimie des Matériaux, 7021, Bizerte, Tunisia
2University of Monastir, Laboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, Monastir 5079, Tunisia
3Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) − UMR 6226, F-35000, Rennes, France

Tài liệu tham khảo

Englebienne, 2005, Goldeconductive polymer nanoparticles: a hybrid material with enhanced photonic reactivity to environmental stimuli, J. Colloid Interface Sci., 292, 445, 10.1016/j.jcis.2005.06.001 Müller, 1995, Supramolecular inorganic chemistry: small guests in small and large hosts, Angew. Chem., Int. Ed. Engl., 34, 2328, 10.1002/anie.199523281 Li, 2013, Processable polyaniline/titania nanocomposites with good photocatalytic and conductivity properties prepared via peroxotitanium complex catalyzed emulsion polymerization approach, Appl. Surf. Sci., 273, 135, 10.1016/j.apsusc.2013.01.213 Gribble, 1984, Synthesis and dielsalder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine, J. Org. Chem., 49, 4518, 10.1021/jo00197a039 Müller, 1998, Polyoxometalates: very large clusters-nanoscale magnets, Chem. Rev., 98, 239, 10.1021/cr9603946 Novena, 2016, Improved solubility and bioactivity oftheophylline (a bronchodilator drug) through its new nitrate salt analysed by experimental and theoretical approaches, J. Mol. Struct., 1116, 45, 10.1016/j.molstruc.2016.03.014 Braun, 1999, Nanostructure templating in inorganic solids with organic lyotropic liquid crystals, J. Am. Chem. Soc., 121, 7302, 10.1021/ja9833725 Daniel, 2004, Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology, Chem. Rev., 104, 293, 10.1021/cr030698+ Bogaert, 1994, Clinical pharmacokinetics of nitrates, Cardiovasc. Drugs Ther., 8, 693, 10.1007/BF00877116 2012 Brandan, 2012, A structural and vibrational study of the chromyl chlorosulfate, fluorosulfate, and nitrate compounds, vol. 1, 3311 2015 Castillo, 2011, Theoretical structural and experimental vibrational study of niobyl nitrate, J. Mol. Struct., 994, 202, 10.1016/j.molstruc.2011.03.018 Torfgård, 1994, Mechanisms of action of nitrates, Cardiovasc. Drugs Ther., 8, 701, 10.1007/BF00877117 Gatfaoui, 2017, Synthesis, characterization, Hirshfeld surface analysis and antioxidant activity of a novel organic-inorganic hybrid material 1-methylpiperazine-1,4-diium bis(nitrate), J. Mol. Struct., 1139, 52, 10.1016/j.molstruc.2017.03.028 Gatfaoui, 2017, Synthesis, structural and spectroscopic features, and investigation of bioactive nature of a novel organic-inorganic hybrid material 1H-1,2,4-triazole-4-ium trioxonitrate, J. Mol. Struct., 1150, 242, 10.1016/j.molstruc.2017.08.092 Sotriffer, 2000, Automated docking of ligand to antibodies: methods and applications, Methods, 20, 280, 10.1006/meth.1999.0922 Coupez, 2006, Docking and scoring theoretically easy, practically impossible, Curr. Med. Chem., 13, 2995, 10.2174/092986706778521797 Noureddine, 2020, Structural, docking and spectroscopic studies of a new piperazine derivative, 1-phenylpiperazine-1,4-diium-bis (hydrogen sulfate), J. Mol. Struct., 1202, 127351, 10.1016/j.molstruc.2019.127351 Carlson, 2000, Accomodating protein flexibility in computational drug design, Mol. Pharmacol., 57, 213 Halperin, 2002, Principles of docking: an overview of search algorithms and a guide to scoring functions, Proteins: Struct. Func. Bioinfo., 47, 409, 10.1002/prot.10115 Abagyan, 2001, High-throughput docking for lead generation, Curr. Opin. Chem. Biol., 5, 375, 10.1016/S1367-5931(00)00217-9 Bruker, 2006 Altomare, 1999, J. Appl. Crystallogr., 32, 115, 10.1107/S0021889898007717 Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Crystallogr., C71, 3 Farrugia, 2012, WinGX and ORTEP for windows: an update, J. Appl. Crystallogr., 45, 849, 10.1107/S0021889812029111 Brandenburg, 1998 Wolff, 2013, 3.1 Frisch, 2009 Becke, 1993, Becke's three parameter hybrid method using the LYP correlation functional, J. Chem. Phys., 98, 5648, 10.1063/1.464913 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Runge, 1984, Phys. Rev. Lett., 52, 997, 10.1103/PhysRevLett.52.997 Humphrey, 1996, VMD—visual molecular dynamics, J. Mol. Graph., 14, 10.1016/0263-7855(96)00018-5 Glendening, 1996, 1990 Yang, 2004, GEMDOCK: a generic evolutionary method for molecular docking, Proteins Struct. Funct. Bioinforma., 55, 288, 10.1002/prot.20035 Visualizer, 2005, Accelrys software inc, Discovery Studio Visualizer, 2 Gatfaoui, 2013, 4-Methylbenzylammonium nitrate, Acta Crystallogr., E69, o1453 Gatfaoui, 2014, 1,1,4,7,7-Pentamethyldiethylenetriammonium trinitrate, Acta Crystallogr., E70, o198 Gatfaoui, 2014, Acta Crystallogr., E70, o398 Gatfaoui, 2014, Dopaminium nitrate, Acta Crystallogr., E70, o571 Gatfaoui, 2014, trans-2,5-Dimethylpiperazine-1,4-diium dinitrate, Acta Crystallogr., E70, o725 Ben M'leh, 2018, Synthesis, molecular structure, vibrational and theoretical studies of a new non-centrosymmetric organic sulphate with promising NLO properties, J. Mol. Struct., 1171, 771, 10.1016/j.molstruc.2018.06.041 Brown, 1976, Acta Crystallogr., A32, 24, 10.1107/S0567739476000041 Blessing, 1986, Acta Crystallogr., B42, 613, 10.1107/S0108768186097641 Gatfaoui, 2019, A proton transfer compound template phenylethylamine: synthesis, a collective experimental and theoretical investigations, J. Mol. Struct., 1191, 183, 10.1016/j.molstruc.2019.04.093 Gatfaoui, 2018, Synthesis and characterization of p-xylylenediaminium bis(nitrate).Effects of the coordination modes of nitrate groups on their structural and vibrational properties, J. Mol. Struct., 1151, 152, 10.1016/j.molstruc.2017.09.027 Bader, 1990 E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, R. Molins, J. Chem. Phys. Lett., 336. Majerz, 2004, Acta Crystallogr., B60, 406, 10.1107/S0108768104010365 Popelier, 1994, J. Phys. Chem., 98, 4473, 10.1021/j100067a040 Koch, 1995, J. Phys. Chem., 99, 9747, 10.1021/j100024a016 Espinosa, 2001, J. Chem. Phys. Lett., 336, 457, 10.1016/S0009-2614(01)00178-6 Rozas, 2000, Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors, J. Am. Chem. Soc., 122, 11154, 10.1021/ja0017864 Johnson, 2010, J. Am. Chem. Soc., 132, 6498, 10.1021/ja100936w Mulliken, 1934, J. Chem. Phys., 2, 782, 10.1063/1.1749394 Pearson, 1997 Parr, 1999, J. Am. Chem. Soc., 121, 1922, 10.1021/ja983494x Reed, 1985, J. Chem. Phys., 83, 1736, 10.1063/1.449360 Kosar, 2011, Spectrochim. Acta, A78, 160, 10.1016/j.saa.2010.09.016 Gunasekaran, 2008, J. Chem. Sci., 120, 315, 10.1007/s12039-008-0054-8 Mulliken, 1955, J. Chem. Phys., 23, 1833, 10.1063/1.1740588 https://doi.org/10.2210/pdb6W63/pdb. https://doi.org/10.2210/pdb6W4B/pdb. Kose, 2018, J. Mol. Struct., 10, 2 Weinhold, 2005