7,7′-Bis[(aza-18-crown-6)carbonyl]thioindigo: Synthesis, Experimental, Theoretical Characterization and Biological Activities

Anahtar Kelimeler:

7, 7\’-bis[(aza-18-crown-6)carbonyl]thioindigo, dft, biological effects, mep

7,7′-Bis[(aza-18-crown-6)carbonyl]thioindigo: Synthesis, Experimental, Theoretical Characterization and Biological Activities

This work presents the characterization of 7,7'-Bis[(aza-18-crown-6)carbonyl]thioindigo (I) by quantum chemical calculations and spectral techniques. The molecular geometry, frontier molecular orbitals (FMO), molecular electrostatic potentials (MEP) and nonlinear optical properties of I in the ground state have been calculated using the density functional method (B3LYP) with the 6−31G(d,p) basis set. The calculated results show that the optimized geometry can well reproduce the crystal structure. The predicted non-linear optical properties of I are greater than ones of urea. The title compound has been tested in vitro for biological effects. The title compound was found to exhibit significant antimicrobial and antioxidant activity

Keywords:

7, 7\’-bis[(aza-18-crown-6)carbonyl]thioindigo, dft, biological effects, mep,

PDF

___

Hong J, Song J, Ham S. Molecular recognition of ammonium ion by tetrahomodioxacalix[4]biscrown. Tetrahedron Lett. 2007; 48:1327-30.
Anderson JD, Paulsen ES, Dearden DV. Alkali metal binding energies of dibenzo18-crown-6: experimental and computational results. Int. J. Mass Spectrom. 2003; 227:63-76.
Brodbelt J, Maleknia S. Gas-Phase selectivities of crown ethers for alkali-metal ion complexation. J. Am. Chem. Soc. 1192; 114:4295-8.
Takeda Y, Hashimoto K, Yoshiyama D, Katsuta S. Extraction of alkali metal (Li, Na, K) Picrates with benzo-15-crown-5 into various organic solvents. Elucidation of fundamental equilibria determining the extraction-ability and –selectivity. J. Incl. Phenom. Macro. 2002; 42:313-21.
Bourgoin M, Wong KH, HUI JY, SMID J. Interactions of macrobicyclic polyethers with ions and ion-pairs of picrate salts. J. Am. Chem. Soc. 1975; 97:3462-7.
Bandyopadhyay R, Cooper BFT, Rossini AJ, Schurko RW, Macdonald CLB. J. Organomet. Chem. 2010; 695:1012-8.
Dubonosov AD, Minkin VI, Bren VA, Shepelenko EN, Tsukanov AV, Starikov AG, Borodkin GS. Tautomeric crown-containing chemosensors for alkali-earth metal cations. Tetrahedron. 2008; 64:3160-7.
Sukwattanasinitt M, Rojanathanes R, Tuntulani T, Sritana-Anant Y, Ruangpornvisuti V. Synthesis of stilbene crown ether p-tert-butylcalix[4]arenes. Tetrahedron Lett. 2001; 42:5291-3.
Lehn JM. Perspectives in supramolecular chemistry – from molecular recognition towards molecular information-processing and self-organization. Angew. Chem. Int. Edit. 1990; 29:1304-19.
Proft FD, Geerlings P. Conceptual and computational DFT in the study of aromaticity. Chem. Rev. 2001; 101:1451-64.
Orek C, Koparir P, Koparir M. N-Cyclohexyl-2-[5-(4-pyridyl)-4-(p-tolyl)-4H-1,2,4triazol-3-ylsulfanyl]-acetamide dihydrate:Synthesis, experimental, theoretical characterization and biological activities. Spectrochim Acta. A. 2012; 97:923-34.
Cansiz A, Cetin A, Orek C, Karatep M, Sarac K, Kus A, Koparir P. 6-Phenyl-3-(4pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, experimental, theoretical characterization and biological activities. Spectrochim Acta. A. 2012; 97:607-15.
Tanak H. DFT computational modeling studies on 4-(2,3Dihydroxybenzylideneamino)-3-methyl-1H-1,2,4-triazol-5(4H)-one. Computational And Theoretical Chemistry. 2011; 967:93-101.
Andzelm J, Fitzgerald G. Chemical Applications of Density Funtional Theory Comparison to Experiment, Hartree-Fock, and Perturbation-Theory. J. Phys. Chem. Andzelm J, Wimmer E. Density Functional Gaussian-Type-Orbital Approach to Molecular Geometries, Vibrations, and Reaction Energies. J. Chem. Phys. 1992; 96:1280-303.
Bien JT, Shang MY, Smith BD. 7,7'-bis[(aza-18-crown-6)carbonyl]thio-indigo. Acta Crystallogr. C. 1996; 52(1):183-6.
Schlegel HB. Optimization of Equilibrium Geometries and Transition Structure. Journal of Computional Chemistry. 1996; 3:214-8.
Peng C, Ayala PY, Schlegel HB. Using Redundant Internal Coordinates to Optimize Equilibrium Geometries and Transition States. Journal of Computational Chemistry. 1996; 17:49-56.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyata K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honca Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Strarmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J and Fox DJ, Gaussian Inc, Wallingford CT.2009.
Woods GL, Washington JA, Antibacterial susceptibility tests: dilution and disk diffusion methods, in: Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken RH, eds, 6th ed. American Society for Microbiology, Washington, 1995;1327-41.
Roberts J. The Cephalosporins in Kirk-Othmer Encyclopedia of Chemical Technology. 3nd ed. John Wiley & Sons Inc., 1992;28-82
M.M. Hossain, M.F. Aziz, R. Ahmed, M. Hossain, A. Mahmuda, T. Ahmed, M.H. Mazumder, Int. J. Pharm. Sci. 2 (2010) 60–3.
Haasewessel W, Ohmasa M, Süsse P. Thioindigo – crystal structural data for modification-2. Naturwissenschaften. 1977; 64:435
Süsse P, Neuling H. Crystal-structure of 7,7’-dimethylthioindigp. Z. Kristallogr. Gokel GW, Garcia BJ. Crown-cation complex effects .3. chemistry and complexes of monoaza-18-crown-6. Tetrahedron Lett. 1977; 77:317-28.
Tanak H. Crystal Structure, Spectroscopy, and Quantum Chemical Studies of €-2[(2Chlorophenyl)iminomethyl]-4-trifluoromethoxyphenol. Journal of Physical Chemistrya. 2011; 115:13865-76.
Politzer P, Murray JS. Theoretical biochemistry and molecular biophysics: a comprehensive survey. Adenine Press, Schenectady, NY, 1991.
Politzer P, Murray JS. The Fundamental Nature and Role of the Electorstatic Potential in Atoms and Molecules. Theor. Chem. Acc. 2002; 108:34.
Amalanathan M, Rastogi VK, Joe IH, Palafox MA, Tomar R. Density functional theory calculations and vibrational spectral analysis of 3,5-(dinitrobenzoic acid). Spectrochim Acta A. 2009; 78:1437-44.
Padmaja L, Ravikumar C, Sajan D, Joe IH, Jayakumar VS, Pettit GR, Nielsen OF. Density Functional Study on the Structural Conformations and Intramolecular Charge transfer From the Vibrational Spectra of the Anticancer Drug Combretastatin. J. Raman. Spectrosc. 2009; 40:419-28.
Sagdinc S, Pir H. Spectroscopic and DFT studies of flurbiprofen as dimer and its Cu(II) and Hg(II) complexes. Spectrochim Acta A. 2009; 73:181-7.
Thanthiriwatte KS, de Silva KMN. Non-linear Optical Properties of Novel Fluorenyl Derivatives - ab Initio Quantum Chemical Calculations. J. Mol. Struc-Theochem. 2002; 617:169-75.
Maroulis G, Begue D, Pouchan C. Accurate Dipole Polarizabilities of Small Silicon Clusters From ab Initio and Density Functional Theory Calculations. Journall of Chemical Physics. 2003; 119:794-8.
Maroulis G. How Large is the Static Electric (hyper)Polarizability Anisotropy in HXeI. Journal of Chemical Physics. 2008; 129:044313-21.
Qin C, Si Y, Yang G, Su Z. Quantum Chemical Study of Structures, Electronic Spectrum, and Nonlinear Optical Properties of Polynuclear Lithium Compounds. Computational and Theoretical Chemistry. 2011; 966:14-9.
Bondet V, Brandwilliams W, Berset C. Kinetics and mechanisms of antioxidant activity using the DPPH free radical method. Food Science and TechnologyLebensmittel-Wissenschaft & Technologie. 1997; 30:609-15.