Synthesis, spectral and quantum mechanical studies and molecular docking studies of Schiff base (E)2-hydroxy-5-(((4-(N-pyrimidin-2-yl)sulfamoyl)phenyl)imino)methyl benzoic acid from 5-formyl salicylic acid and sulfadiazine

Wang, 2010, Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities, Eur. J. Med. Chem., 45, 4631, 10.1016/j.ejmech.2010.07.031 Actor, 2000, Chemotherapeutics Smilack, 1999, Trimethoprim-sulfamethoxazole, Mayo Clin. Proc., 74, 730, 10.4065/74.7.730 Ong, 2010, Mycobacterium tuberculosis and sulfamethoxazole susceptibility, Antimicrob. Agents Chemother., 54, 2748, 10.1128/AAC.00029-10 Schiff, 1864, Mittheilungen aus dem Universitätslaboratorium in Pisa: eine neue Reihe organischer Basen, Justus Liebigs Ann. Chem., 131, 118, 10.1002/jlac.18641310113 Fabbrizzi, 2020, Beauty in chemistry: making artistic molecules with Schiff bases, J. Org. Chem., 85, 12212, 10.1021/acs.joc.0c01420 Kajal, 2013, Schiff bases: a versatile pharmacophore, J. Catal., 2013, 893512 da Silva, 2011, Schiff bases: a short review of their antimicrobial activities, J. Adv. Res., 2, 1, 10.1016/j.jare.2010.05.004 Sondhi, 2006, Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases, Bioorg. Med. Chem., 14, 3758, 10.1016/j.bmc.2006.01.054 Miri, 2013, QM study and conformational analysis of an isatin Schiff base as a potential cytotoxic agent, J. Mol. Model., 19, 727, 10.1007/s00894-012-1586-x Al Zoubi, 2017, Schiff bases and their complexes: recent progress in thermal analysis, Separ. Sci. Technol., 52, 1052, 10.1080/01496395.2016.1267756 Chohan, 1997, Structural and biological behaviour of Co(II), Cu(II) and Ni(II) metal complexes of some amino acid derived schiff-bases, Met. Based. Drugs., 4, 803138, 10.1155/MBD.1997.267 Kirubavathy, 2017, Structural and molecular docking studies of biologically active mercaptopyrimidine Schiff bases, J. Mol. Struct., 1127, 345, 10.1016/j.molstruc.2016.07.082 Pandeya, 1999, Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine, Farm, 54, 624, 10.1016/S0014-827X(99)00075-0 Tomma, 2014, Synthesis and characterization of novel Schiff bases containing pyrimidine unit, Arab. J. Chem., 7, 157, 10.1016/j.arabjc.2013.08.024 Issa, 2011, Charge–transfer complexes of pyrimidine Schiff bases with aromatic nitro compounds, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 79, 513, 10.1016/j.saa.2011.03.022 Qin, 2013, Schiff bases: a short survey on an evergreen chemistry tool, Molecules, 18, 12264, 10.3390/molecules181012264 Mumit, 2020, DFT studies on vibrational and electronic spectra, HOMO–LUMO, MEP, HOMA, NBO and molecular docking analysis of benzyl-3-N-(2,4,5-trimethoxyphenylmethylene)hydrazinecarbodithioate, J. Mol. Struct., 1220, 128715, 10.1016/j.molstruc.2020.128715 Ommenya, 2020, Characterization and antibacterial activity of Schiff base, 4-chloro-2-{(E)-[(4-Fluorophenyl)imino]methyl}phenol metal (II) complexes, J. Chem., 2020, 1745236 Omidi, 2020, A review on biological activities of Schiff base{,} hydrazone{,} and oxime derivatives of curcumin, RSC Adv., 10, 30186, 10.1039/D0RA05720G Haruna Veena, 2019, Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea, Heliyon, 5 Mary, 2019, Detailed quantum mechanical, molecular docking, QSAR prediction, photovoltaic light harvesting efficiency analysis of benzil and its halogenated analogues, Heliyon, 5, 10.1016/j.heliyon.2019.e02825 Elangovan, 2021, Synthesis, structural investigation, computational study, antimicrobial activity and molecular docking studies of novel synthesized (E)-4-((pyridine-4-ylmethylene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide from pyridine-4-carboxaldehyde and sulfadiazine, J. Mol. Struct., 1241, 130544, 10.1016/j.molstruc.2021.130544 Sureshkumar, 2018, Spectroscopic analysis of 8-hydroxyquinoline derivatives and investigation of its reactive properties by DFT and molecular dynamics simulations, J. Mol. Struct., 1156, 336, 10.1016/j.molstruc.2017.11.120 Armaković, 2012, Active components of frequently used β-blockers from the aspect of computational study, J. Mol. Model., 18, 4491, 10.1007/s00894-012-1457-5 Haruna, 2020, Spectral characterization, thermochemical studies, periodic SAPT calculations and detailed quantum mechanical profiling various physico-chemical properties of 3, 4-dichlorodiuron, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 228, 117580, 10.1016/j.saa.2019.117580 Frisch, 2013 Dennington, 2009 Becke, 2014, Perspective: fifty years of density-functional theory in chemical physics, J. Chem. Phys., 140, 18A301, 10.1063/1.4869598 Becke, 1988, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev., 38, 3098, 10.1103/PhysRevA.38.3098 Schmider, 2000, Chemical content of the kinetic energy density, J. Mol. Struct. THEOCHEM., 527, 51, 10.1016/S0166-1280(00)00477-2 Becke, 1993, A new mixing of Hartree-Fock and local density-functional theories, J. Chem. Phys., 98, 1372, 10.1063/1.464304 Becke, 2005, Exchange-hole dipole moment and the dispersion interaction, J. Chem. Phys., 122, 154104, 10.1063/1.1884601 Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913 Dunning, 1970, Gaussian basis functions for use in molecular calculations. I. Contraction of (9s5p) atomic basis sets for the first-row atoms, J. Chem. Phys., 53, 2823, 10.1063/1.1674408 Dunning, 1989, Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen, J. Chem. Phys., 90, 1007, 10.1063/1.456153 Kendall, 1992, Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions, J. Chem. Phys., 96, 6796, 10.1063/1.462569 Sets, 2008, 115 Jamróz, 2013, Vibrational energy distribution analysis (VEDA): scopes and limitations, spectrochim, Acta Part A Mol. Biomol. Spectrosc., 114, 220, 10.1016/j.saa.2013.05.096 Jamroz, 2004, Vibrational Energy Distribution Analysis VEDA, 4 Trott, 2010, Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31, 455, 10.1002/jcc.21334 Morris, 2009, AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility, J. Comput. Chem., 30, 2785, 10.1002/jcc.21256 Discovery Studio, 2017 Lu, 2012, Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33, 580, 10.1002/jcc.22885 Surendar, 2021, Quasi liquid Schiff bases from trans -2-hexenal and cytosine and l -leucine with potential antieczematic and antiarthritic activities ​: synthesis , structure and quantum mechanical studies, J. Mol. Liq., 334, 116448, 10.1016/j.molliq.2021.116448 Burke, 2013, DFT in a nutshell, Int. J. Quant. Chem., 113, 96, 10.1002/qua.24259 Politzer, 2021, Electrostatic potentials at the nuclei of atoms and molecules, Theor. Chem. Acc., 140, 7, 10.1007/s00214-020-02701-0 Politzer, 1991, Molecular electrostatic potentials and chemical reactivity, Rev. Comput. Chem., 273, 10.1002/9780470125793.ch7 Politzer, 2002, The fundamental nature and role of the electrostatic potential in atoms and molecules, Theor. Chem. Acc., 108, 134, 10.1007/s00214-002-0363-9 Carbó-Dorca, 2004, Quantum mechanical basis for mulliken population analysis, J. Math. Chem., 36, 231, 10.1023/B:JOMC.0000044221.23647.20 Ed Glendening, 2003 Srikanth, 2020, Detailed molecular structure (XRD), conformational search, spectroscopic characterization (IR, Raman, UV, fluorescence), quantum mechanical properties and bioactivity prediction of a pyrrole analogue, Heliyon, 6, 10.1016/j.heliyon.2020.e04106 Alsalme, 2021, Structural, physico-chemical landscapes, ground state and excited state properties in different solvent atmosphere of Avapritinib and its ultrasensitive detection using SERS/GERS on self-assembly formation with graphene quantum dots, J. Mol. Liq., 322, 114555, 10.1016/j.molliq.2020.114555 Al-Zaqri, 2020, First-Principle studies of istradefylline with emphasis on the stability, reactivity, interactions and wavefunction-dependent properties, Polycycl. Aromat. Comp., 1, 10.1080/10406638.2020.1857273 Pooventhiran, 2021, Structural aspects, conformational preference and other physico-chemical properties of Artesunate and the formation of self-assembly with graphene quantum dots: a first principle analysis and surface enhancement of Raman activity investigation, J. Mol. Liq., 325, 114810, 10.1016/j.molliq.2020.114810 Al-Zaqri, 2021, Structural investigations, quantum mechanical studies on proton and metal affinity and biological activity predictions of selpercatinib, J. Mol. Liq., 325, 114765, 10.1016/j.molliq.2020.114765 Kyriakidou, 2017, Natural bond orbitals: local sets showing minimal intra-pair correlations and minimal unpaired electron populations, Comput. Theor. Chem., 1100, 1, 10.1016/j.comptc.2016.11.017 Reed, 1988, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint, Chem. Rev., 88, 899, 10.1021/cr00088a005 Dunnington, 2012, Generalization of natural bond orbital analysis to periodic systems: applications to solids and surfaces via plane-wave density functional theory, J. Chem. Theor. Comput., 8, 1902, 10.1021/ct300002t Liakos, 2015, Exploring the accuracy limits of local pair natural orbital coupled-cluster theory, J. Chem. Theor. Comput., 11, 1525, 10.1021/ct501129s Weinhold, 2012, Natural bond orbital analysis: a critical overview of relationships to alternative bonding perspectives, J. Comput. Chem., 33, 2363, 10.1002/jcc.23060 Glendening, 2012, Natural bond orbital methods, WIREs Comput. Mol. Sci., 2, 1, 10.1002/wcms.51 Alsalme, 2020, Modelling the structural and reactivity landscapes of tucatinib with special reference to its wavefunction-dependent properties and screening for potential antiviral activity, J. Mol. Model., 26, 341, 10.1007/s00894-020-04603-1 Pooventhiran, 2021, Detailed structural examination, quantum mechanical studies of the aromatic compound solarimfetol and formation of inclusion compound with cucurbituril, Polycycl. Aromat. Comp., 1, 10.1080/10406638.2021.1937238 Bhattacharyya, 2021, Adsorption of the drug bempedoic acid over different 2D/3D nanosurfaces and enhancement of Raman activity enabling ultrasensitive detection: first principle analysis, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 119630, 10.1016/j.saa.2021.119630 Al-Zaqri, 2020, Structural and physico-chemical evaluation of melatonin and its solution-state excited properties, with emphasis on its binding with novel coronavirus proteins, J. Mol. Liq., 318, 114082, 10.1016/j.molliq.2020.114082 Alharthi, 2021, Excited-state electronic properties, structural studies, noncovalent interactions, and inhibition of the novel severe acute respiratory syndrome coronavirus 2 proteins in Ripretinib by first-principle simulations, J. Mol. Liq., 324, 115134, 10.1016/j.molliq.2020.115134 Jacobsen, 2008, Localized-orbital locator (LOL) profiles of chemical bonding, Can. J. Chem., 86, 695, 10.1139/v08-052 Rizwana, 2019, Molecular docking studies, charge transfer excitation and wave function analyses (ESP, ELF, LOL) on valacyclovir: a potential antiviral drug, Comput. Biol. Chem., 78, 9, 10.1016/j.compbiolchem.2018.11.014 Koumpouras, 2020, Distinguishing between chemical bonding and physical binding using electron localization function (ELF), J. Phys. Condens. Matter, 32, 315502, 10.1088/1361-648X/ab7fd8 Fuster, 2000, Topological analysis of the electron localization function (ELF) applied to the electrophilic aromatic substitution, J. Phys. Chem., 104, 852, 10.1021/jp992783k Fuentealba, 2007, Chapter 5 Understanding and using the electron localization function, 57 V Gibbs, 2003, The electron localization function: a tool for locating favorable proton docking sites in the silica polymorphs, Phys. Chem. Miner., 30, 305, 10.1007/s00269-003-0318-2 Domingo, 2016, Applications of the conceptual density functional theory indices to organic chemistry reactivity, Molecules, 21, 748, 10.3390/molecules21060748 Lefebvre, 2017, Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient: versus electron density, Phys. Chem. Chem. Phys., 19, 17928, 10.1039/C7CP02110K Boto, 2017, Revealing strong interactions with the reduced density gradient: a benchmark for covalent, ionic and charge-shift bonds, Theor. Chem. Acc., 136, 1, 10.1007/s00214-017-2169-9 Pooventhiran, 2020, Structural aspects, conformational preference and other physico-chemical properties of Artesunate and the formation of self-assembly with graphene quantum dots: a first principle analysis and surface enhancement of Raman activity investigation, J. Mol. Liq., 114810 Daina, 2017, SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Sci. Rep., 7, 42717, 10.1038/srep42717 Filimonov, 2014, Prediction of the biological activity spectra of organic compounds using the pass online web resource, Chem. Heterocycl. Compd., 50, 444, 10.1007/s10593-014-1496-1 Lagunin, 2000, PASS: prediction of activity spectra for biologically active substances, Bioinformatics, 16, 747, 10.1093/bioinformatics/16.8.747 Tereshko, 2003, Encapsulating Streptomycin within a small 40-mer RNA, Chem. Biol., 10, 175, 10.1016/S1074-5521(03)00024-3 Burley, 2018, RCSB Protein Data Bank: biological macromolecular structures enabling research and education in fundamental biology, biomedicine, biotechnology and energy, Nucleic Acids Res., 47, D464, 10.1093/nar/gky1004