Synthesis, Structural Study and Spectroscopic Characterization of a Quinolin-8-Yloxy Derivative with Potential Biological Properties

Elida Romano, María V. Castillo, Jorgelina L. Pergomet, Juan Zinczuk, Silvia A. Brandán

Chemistry Rosario Institute (CONICET-UNR), Faculty of Biochemistry and Pharmacists Sciences, Rosario, R. Argentina.
Faculty of Biochemistry, Chemistry and Pharmacy of the National University of Tucumán, Tucumán, R. Argentina.

DOI: 10.4236/ojsta.2013.21002                

Abstract

We have prepared the (5-chloro-quinolin-8-yloxy) acetic acid and characterized it by using infrared, Raman and multi-dimensional nuclear magnetic resonance spectroscopies. The density functional theory (DFT) together with the 6-31G* and 6-311++G** basis sets were used to study its structure and vibrational properties. Three stable conformations of the compound were theoretically determined in gas phase and probably these conformations are present in the solid phase. The harmonic vibrational wavenumbers for the optimized geometries were calculated at the same theory levels. For a complete assignment of the observed bands in the vibrational spectra, the DFT calculations were combined with Pulay’s scaled quantum mechanical force field (SQMFF) methodology in order to fit the theoretical wavenumber values to the experimental ones. Besides, the force constants of the three conformers of (5-chloro-quinolin-8-yloxy) acetic acid were calculated and compared with those obtained by us for the 2-(quinolin-8-yloxy) acetic acid. In addition, the characteristics of the electronic delocalization of those structures were performed by using natural bond orbital (NBO), while the corresponding topological properties of electronic charge density are analysed by employing Bader’s atoms in molecules theory (AIM).

Keywords

(5-Chloro-Quinolin-8-Yloxy) Acetic Acid; Vibrational Spectra; Molecular Structure; Force Field; DFT Calculations

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. Y. Cho, J. H. Ahn, J. D. Ha, S. K. Kang, J. Y. Baek, S. S. Han, E. Y. Shin, S. S. Kim, K. R. Kim, H. G. Cheon and J. K. Choi, “Protein Tyrosine Phosphatase 1B Inhibitors: Heterocyclic Carboxylic Acids,” Bulletin of the Korean Chemical Society, Vol. 24, No. 10, 2003, pp. 1455-1464. doi:10.5012/bkcs.2003.24.10.1455
[2]	B. P. Kennedy and C. Ramachandran, “Protein Tyrosine Phosphatase-1B in Diabetes,” Biochemical Pharmacology, Vol. 60, No. 7, 2000, pp. 877-883. doi:10.1016/S0006-2952(00)00305-1
[3]	N. Moller, L. Iversen, H. Andersen, J. McCormack, “Protein Tyrosine Phosphatases (PTPs) as Drug Targets: Inhibitors of PTP-1 for the Treatment of Diabetes,” Current Opinion in Drug Discovery & Development, Vol. 3, No. 5, 2000, pp. 527-540.
[4]	A. Hubele, “Use of Quinoline Derivatives for the Protection of Cultivated Plants from Herbicides,”US Patent No. 4902340, 1990.
[5]	F. Hayat, A. Salahuddin, J. Zargan and A. Azam, “Synthesis, Characterization, Antiamoebic Activity and Cytotoxicity of Novel 2-(Quinolin-8-Yloxy) Acetohydrazones and Their Cyclized Products (1,2,3-Thiadiazole and 1,2,3-Selenadiazole Derivatives),” European Journal of Medicinal Chemistry, Vol. 45, No. 12, 2010, pp. 6127-6134. doi:10.1016/j.ejmech.2010.09.066
[6]	G. R. Arga?araz, E. Romano, J. Zinczuk and S. A. Brandán, “Structural and Vibrational Study of 2-(Quinolin-8-yloxy)-Acetic Acid Based on FT-IR-Raman Spectroscopy and DFT Calculations,” Journal of Chemistry and Chemical Engineering, Vol. 5, No. 8, 2011, pp. 747-758.
[7]	P. Pulay, G. Fogarasi, F. Pang and E. J. Boggs, “Systematic ab Initio Gradient Calculation of Molecular Geometries, Force Constants, and Dipole Moment Derivatives,” Journal of the American Chemical Society, Vol. 101, No. 10, 1979, pp. 2550-2560. doi:10.1021/ja00504a009
[8]	P. Pulay, G. Fogarasi, G. Pongor, J. E. Boggs and A. Vargha, “Combination of Theoretical ab Initio and Experimental Information to Obtain Reliable Harmonic Force Constants. Scaled Quantum Mechanical (QM) Force Fields for Glyoxal, Acrolein, Butadiene, Formaldehyde, and Ethylene,” Journal of the American Chemical Society, Vol. 105, No. 24, 1983, pp. 7037-7047. doi:10.1021/ja00362a005
[9]	G. Rauhut and P. Pulay, “Transferable Scaling Factors for Density Functional Derived Vibrational Force Fields,” The Journal of Physical Chemistry, Vol. 99, No. 39, 1995, pp. 3093-3100. doi:10.1021/j100039a056
[10]	A. E. Reed, L. A. Curtis and F. Weinhold, “Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint,” Chemical Review, Vol. 88, No. 6, 1988, pp. 899-926. doi:10.1021/cr00088a005
[11]	J. P. Foster and F. J. Weinhold, “Natural Hybrid Orbitals,” Journal of the American Chemical Society, Vol. 102, No. 24, 1980, pp. 7211-7218. doi:10.1021/ja00544a007
[12]	A. E. Reed and F. Weinhold, “Natural Localized Molecular Orbitals,” Chemical Physics, Vol. 83, No. 4, 1985, pp. 1736-1740.
[13]	R. F. W. Bader, “Atoms in Molecules: A Quantum Theory,” Oxford University Press, Oxford, 1990.
[14]	F. Sun, L. Chen, H. C. Fang, X. M. Lin and Y. P. Cai, “8-(Carboxymethoxy)Quinolinium Nitrate Monohydrate,” Acta Crystallographica, Vol. 64, 2008, p. 1641.
[15]	F. Biegler-K?ning, J. Sch?nbohm and D. Bayles, “AIM 2000—A Program to Analyze and Visualize Atoms in Molecules,” Journal of Computational Chemistry, Vol. 22, No. 5, 2001, pp. 545-559.
[16]	E. D. Glendening, J. K. Badenhoop, A. D. Reed, J. E. Carpenter and F. Weinhold, “Natural Bond Orbital: NBO 3.1,” University of Wisconsin, Madison, 1996.
[17]	M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, “Gaussian 03, Revision B.01,” Gaussian, Inc., Pittsburgh, 2003.
[18]	G. Fogarasi, X. Zhou, P. Taylor and P. Pulay, “The Calculation of Ab Initio Molecular Geometries: Efficient Optimization by Natural Internal Coordinates and Empirical Correction by Offset Forces,” Journal of the American Chemical Society, Vol. 114, No. 21, 1992, pp. 8191-8201. doi:10.1021/ja00047a032
[19]	T. Sundius, “Molvib—A Flexible Program for Force Field Calculations,” Journal of Molecular Structure, Vol. 218, No.1-2, 1990, pp. 321-326. doi:10.1016/0022-2860(90)80287-T
[20]	T. Sundius, “Scaling of Ab Initio Force Fields by MOLVIB,” Vibrational Spectroscopy, Vol. 29, No. 1-2, 2002, pp. 89-95. doi:10.1016/S0924-2031(01)00189-8
[21]	F. Kalincsák and G. Pongor, “Extension of the Density Functional Derived Scaled Quantum Mechanical Force Field Procedure,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 58, No. 5, 2002, pp. 999-1011. doi:10.1016/S1386-1425(01)00572-8
[22]	A. B. Nielsen and A. J. Holder, “Gauss View, User’s Reference,” GAUSSIAN, Inc., Pittsburgh, 1997-1998.
[23]	A. E. Ledesma, S. A. Brandán, J. Zinczuk, O. Piro, J. J. L. González, A. B. Altabef, “Structural and Vibrational Study of 2-(2’-Furyl)-1H-Imidazole,” Journal of Physical Organic Chemistry, Vol. 21, No. 12, 2008, pp. 1086-1097. doi:10.1002/poc.1449
[24]	E. Romano, A. B. Raschi, A. Benavente and S. A. Brandán, “Structural Analysis, Vibrational Spectra and Coordinated Normal of 2R-(?)-6-Hydroxytremetone,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 84, No. 1, 2011, pp. 111-116. doi:10.1016/j.saa.2011.09.011
[25]	S. A. Brandán, G. Benzal, et al., “Theoretical and Experimental Atudy of the Vibrational Apectra of 1,5-Simethylcytosine,” Vibrational Spectroscopy, Vol. 46, No. 2, 2008, pp. 89-99. doi:10.1016/j.vibspec.2007.11.001
[26]	A. E. Ledesma, J. Zinczuk, A. B. Altabef, J. J. López-González and S. A. Brandán, “Synthesis and Vibrational Analysis of N-(2’-Furyl)-Imidazole,” Journal of Raman Spectroscopy, Vol. 40, No. 8, 2009, pp. 1004-1010.
[27]	J. Zinczuk, A. E. Ledesma, S. A. Brandán, O. E. Piro, J. J. López-González, A. B. Altabef, “Structural and Vibrational Study of 2-(2’-Furyl)-4,5-1H-Dihydroimidazole,” Journal of Physical Organic Chemistry, Vol. 22, No. 12, pp. 1166-1167. doi:10.1002/poc.1572
[28]	S. A. Brandán, E. Erog?lu, A. E. Ledesma, O. Oltulu and O. B. Yal??nkaya, “A New Vibrational Study of Acetazolamide Compound Based on Normal Coordinate Analysis and DFT Calculations,” Journal of Molecular Structure, Vol. 993, No. 1-3, 2011, pp. 225-231. doi:10.1016/j.molstruc.2010.11.012
[29]	L. C. Bichara, H. E. Lanús, C. G. Nieto and S. A. Brandán, “Density Functional Theory Calculations of the Molecular Force Field of l-Ascorbic Acid, Vitamin C,” The Journal of Physical Chemistry A, Vol. 114, No. 14, 2010, pp. 4997-5004. doi:10.1021/jp912251g
[30]	S. A. Brandán, F. M. López and M. Montejo, J. J. L. González, A. B. Altabef, “Theoretical and Experimental Vibrational Spectrum Study of 4-Hydroxybenzoic Acid as Monomer and Dimer,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 75, No. 5, 2010, pp. 1422-1434. doi:10.1016/j.saa.2010.01.012
[31]	A. E. Ledesma, C. Contreras, J. Svoboda, A. Vektariane and S. A. Brandán, “Theoretical Structures and Experimental Vibrational Spectra of Isomeric Benzofused thieno [3,2-b] Furan Compounds,” Journal of Molecular Structure, Vol. 967, No. 1-3, 2010, pp. 159-165. doi:10.1016/j.molstruc.2009.12.050
[32]	C. D. Contreras and M. Montejo, J. J. L. González, J. Zinczuk and S. A. Brandán, “Structural and Vibrational Analyses of 2-(2-Benzofuranyl)-2-Imidazoline,” Journal of Raman Spectroscopy, Vol. 42, No. 1, 2011, pp. 108-116. doi:10.1002/jrs.2659
[33]	J. Antony, G. V. Helden, G. Meijer and B. Schmidt, “Anharmonic Midinfrared Vibrational Spectra of Benzoic Acid Monomer and Dimer,” Journal of Chemical Physics, Vol. 123, No. 1, 2005, pp. 14305-14311. doi:10.1063/1.1947191
[34]	C. D. Contreras, A. E. Ledesma, H. E. Lanús, J. Zinczuck and S. A. Brandán, “Hydration of L-Tyrosine in Aqueous Medium. An Experimental and Theoretical Study by Mixed Quantum Mechanical/Molecular Mechanics Methods,” Vibrational Spectroscopyc, Vol. 57, No. 1, 2011, pp. 108-115.
[35]	S. Ghose and J. K. Dattagupta, “Crystal Structure of Tolazoline Hydrochloride (Priscoline), an α-Adrenergic Antagonist,” Journal of the Chemical Society, Perkin Transactions 2, Vol. 200, No. 1-2, 1989, pp. 599-601.
[36]	C. D. Contreras, A. E. Ledesma, J. Zinczuk and S. A. Brandán, “Vibrational Study of Tolazoline Hydrochloride by Using FTIR-Raman and DFT Calculations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 79, No. 5, 2011, pp. 1710-1714. doi:10.1016/j.saa.2011.05.041
[37]	E. Romano, M. V. Castillo, J. L. Pergomet, J. Zinczuk and S. A. Brandán, “Synthesis and Structural and Vibrational Analysis of (5,7-Dichloro-Quinolin-8-Yloxy) Acetic Acid,” Journal of Molecular Structure, Vol. 1018, No. 27, 2012, pp. 149-155. doi:10.1016/j.molstruc.2012.03.013