Density functional computational and X-ray studies on pharmaceutical compound 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole

Zarife Sibel Şahin; Mine Yarım; Meriç Köksal

doi:10.5155/eurjchem.8.1.1-7.1512

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Published: Mar 31, 2017

DOI: https://doi.org/10.5155/eurjchem.8.1.1-7.1512

Keywords:

Indole, Piperazine, DFT calculations, Crystal structure, Frontier molecular orbitals, Molecular electrostatic potential map

Section

Research Article

Issue

Vol. 8 No. 1 (2017): March 2017

Dates

Received 2016-12-01
Accepted 2016-12-25
Published 2017-03-31

Zarife Sibel Şahin

Sinop University, Faculty of Engineering and Architectures, Department of Energy Systems Engineering, 57000, Sinop, Turkey

Mine Yarım

Yeditepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34755, Kayışdağı, İstanbul, Turkey

Meriç Köksal

Yeditepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34755, Kayışdağı, İstanbul, Turkey

Abstract

The crystal and molecular structure of 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole (I) has been determined by single-crystal X-ray diffraction. Molecular geometry of compound I in the ground state has been calculated using the density functional method (DFT) with B3LYP/6-31G(d,p) basis set and compared with the experimental data. In addition, density functional calculations of the structure, molecular electrostatic potential map, frontier molecular orbitals, atomic charges, thermodynamic functions and global chemical reactivity descriptors of compound I were performed.

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Şahin, Z. S.; Yarım, M.; Köksal, M. Density Functional Computational and X-Ray Studies on Pharmaceutical Compound 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-Indole. Eur. J. Chem. 2017, 8, 1-7.

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References

[1]. Aydar, E.; Palmer, C. P.; Klyachko, V. A.; Jackson, M. B. Neuron 2002, 34, 399-410.
https://doi.org/10.1016/S0896-6273(02)00677-3

[2]. Jbilo, O.; Vidal, H.; Paul, R.; Nys, N. D.; Bensaid, M.; Silve, S.; Carayon, P.; Davi, D.; Galiegue, S.; Bourrie, B.; Guillemot, J. C.; Ferrara, P.; Loison, G.; Maffrand, J. P.; Le Fur, G.; Casellas, P. J. Biol. Chem. 1997, 272, 27107-27115.
https://doi.org/10.1074/jbc.272.43.27107

[3]. Hanner, M.; Moebius, F. F.; Flandorfer, A. A.; Knaus, H. G.; Striessnig, J.; Kempner, E.; Glossmann, H. Proc. Natl. Acad. Sci. USA 1996, 93, 8072-8077.
https://doi.org/10.1073/pnas.93.15.8072

[4]. Mei, J. F.; Pasternak, G. W. Biochem. Pharmacol 2001, 62, 349-355.
https://doi.org/10.1016/S0006-2952(01)00666-9

[5]. Pan, Y. X.; Mei, J.; Xu, J.; Wan, B. L.; Zuckerman, A.; Pasternak, G. W. J. Neurochem. 1998, 70, 2279-2285.
https://doi.org/10.1046/j.1471-4159.1998.70062279.x

[6]. Seth, P.; Leibach, F. H.; Ganapathy, V. Biochem. Biophys. Res. Commun 1997, 241, 535-540.
https://doi.org/10.1006/bbrc.1997.7840

[7]. Seth, P.; Fei, Y. J.; Li, H. W.; Huang, W.; Leibach, F. H.; Ganapathy, V. J. Neurochem. 1998, 70, 922-931.
https://doi.org/10.1046/j.1471-4159.1998.70030922.x

[8]. Abou-Gharbia, M.; Ablordeppey, S. Y.; Glennon, R. Ann Rep Med Chem. 1993, 28, 1-10.
https://doi.org/10.1016/S0065-7743(08)60871-4

[9]. Hayashi, T.; Su, T. P. CNS Drugs 2004, 18, 269-284.
https://doi.org/10.2165/00023210-200418050-00001

[10]. Sorbera, L. A.; Silvestre, J.; Castaner, J. Drugs Fut. 1999, 24, 133-140.
https://doi.org/10.1358/dof.1999.024.02.474038

[11]. Foster, A.; Wu, H.; Chen, W.; Williams, W.; Bowen, W. D.; Matsumoto, R. R. A. Coop, Bioorg. Med. Chem. Lett. 2003, 13, 749-751.
https://doi.org/10.1016/S0960-894X(02)01034-X

[12]. Matsumoto, R. R.; Liu, Y.; Lerner, M.; Howard, E. W.; Bracket, D. J. Eur. J. Pharmacol. 2003, 469, 1-12.
https://doi.org/10.1016/S0014-2999(03)01723-0

[13]. Matsumoto, R. R.; McCracken, K. A.; Pouw, B.; Miller, J.; Bowen, W. D.; Williams, W.; deCosta, B. R. Eur. J. Pharmacol. 2001, 411, 261-273.
https://doi.org/10.1016/S0014-2999(00)00917-1

[14]. Crawford, K. W.; Bowen, W. D. Cancer Res. 2002, 62, 313-322.

[15]. Spruce, B. A.; Campbell, L. A.; McTavish, N.; Cooper, M. A.; Appleyard, V. L.; O'Neill, M.; Howie, J.; Samson, J.; Watt, S.; Murray, K.; McLean, D.; Leslie, N. R.; Safrany, S. T.; Ferguson, M. R.; Peters, J. A.; Prescott, A. R.; Box, G.; Hayes, A.; Nutley, B.; Raynaud, F.; Downes, C. P.; Lambert, J. J.; Thompson, A. M.; Eccles, S. Cancer Res. 2004, 64, 4875-4886.
https://doi.org/10.1158/0008-5472.CAN-03-3180

[16]. Choi, S. R.; Yang, B.; Plossl, K.; Chumpradit, S.; Wey, S. P.; Acton, P. D.; Wheeler, K.; Mach, R. H.; Kung H. F. Nucl. Med. Biol. 2001, 28, 657-666.
https://doi.org/10.1016/S0969-8051(01)00234-7

[17]. John, C. S.; Lim, B. B.; Vilner, B. J.; Geyer, B. C.; Bowen, W. D. J. Med. Chem. 1998, 41, 2445-2450.
https://doi.org/10.1021/jm9800447

[18]. Lipkowitz, K. B.; Boyd, D. Reviews in Computational Chemistry, Eds.; VCH: New York, Vols. 1-13, 1990-1999.

[19]. Zhang, Y.; Guo, A. J.; You, X. Z. J Am Chem Soc. 2001, 123, 9378-9387.
https://doi.org/10.1021/ja0023938

[20]. Yarim, M.; Koksal, M.; Schepmann, D.; Wünsch, B. Chem Biol Drug Des. 2011, 78(5), 869-875.
https://doi.org/10.1111/j.1747-0285.2011.01215.x

[21]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[22]. Farrugia, L. J. WINGX-A Windows Program for Crystal Structure Analysis, University of Glasgow, 1998.

[23]. Farrugia, L. J. J. Appl Crystallogr. 1999, 30, 837-838.
https://doi.org/10.1107/S0021889899006020

[24]. Mercury, version 3. 0; CCDC, available online via ccdc. cam. ac. uk/products/mercury.

[25]. Spek, A. L. PLATON-A Multipurpose Crystallographic Tool, Utrecht, Utrecht University, The Netherlands, 2005.

[26]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Jr. Montgomery, J. A.; Vreven, J. T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski J. W.; Ayala P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Lui, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W. B.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. GAUSSIAN 03, Revision C. 02, Gaussian Inc, Wallingford CT., 2004.

[27]. Frisch, A.; Dennington II, R. D.; Keith, T. A.; Milliam, J.; Nielsen, A. B.; Holder, A. J.; Hiscocks, J. GaussView Reference, Version 4. 0. Gaussian Inc., Pittsburgh, 2007.

[28]. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 846-864.

[29]. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133-1138.
https://doi.org/10.1103/PhysRev.140.A1133

[30]. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J Comput Chem. 1996, 17, 43-49.
https://doi.org/10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0

[31]. Stephens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J Phys Chem. 1994, 98, 11623-11627.
https://doi.org/10.1021/j100096a001

[32]. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354-1358.
https://doi.org/10.1021/ja00839a011

[33]. Sahin, Z. S.; Isık, S.; Salgın-Goksen, U.; Gokhan-Kelekci, N. Chinese J. Struct. Chem. 2010, 29, 700-705.

[34]. Sahin, Z. S.; Ozkan, I.; Koksal, M.; Isık, S. J. Struct. Chem. 2012, 53, 938-941.
https://doi.org/10.1134/S0022476612050162

[35]. Li, Y.; Sun, H.; Jiang, H.; Xu, N.; Xu, H. Acta Cryst. E 2014, 70, 259-261.
https://doi.org/10.1107/S1600536814020686

[36]. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
https://doi.org/10.1002/anie.199515551

[37]. Leach, A. R. Molecular modelling-Principles and applications, Prentice Hall, 2nd edn, Harlow, 2001.

[38]. Jensen, F. Introduction to computational chemistry, Wiley: 2nd ed. Chichester, UK, 2006.

[39]. Aihara, J. J. Phys. Chem. A 1999, 103, 7487-7495.
https://doi.org/10.1021/jp990092i

[40]. Politzer, P.; Daiker, K. C. Models for Chemical Reactivity. In The Force Concept in Chemisty Van Nostrand Reinhold New York, 1981.

[41]. Cox, S. R.; Williams, D. E. J. Compt. Chem. 1981, 2, 304-323.
https://doi.org/10.1002/jcc.540020312

[42]. Carbo, R.; Calabuig, B. Compt. Phys. Commun. 1989, 55, 117-126.
https://doi.org/10.1016/0010-4655(89)90070-2

[43]. Politzer, P.; Truhlar, D. G. In: Chemical Applications of Atomic and Molecular Electrostatic Potentials Plenum, New York, 1981.
https://doi.org/10.1007/978-1-4757-9634-6

[44]. Scrocco, E.; Tomasi, J. Top. Curr. Chem. 1973, 42, 69-95.

[45]. Sahin, Z. S.; Salgin-Goksen, U.; Gokhan-Kelekci, N.; Isik, S. J. Mol. Struct. 2011, 1006, 147-158.
https://doi.org/10.1016/j.molstruc.2011.08.061

[46]. McQuarrie, D. A. Molecular Thermodynamics, Calif., University Science Books, Sausalito, 1999.

[47]. Hehre, W. J. AB initio Molecular Orbital Theory, Wiley: New York, 1986.

[48]. Li, X. W.; Shibata, E.; Nakamura, T. Materials Trans. 2003, 44-5, 1004-1007.
https://doi.org/10.2320/matertrans.44.1004

[49]. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700.
https://doi.org/10.1021/jp073974n

[50]. Sahin, Z. S.; Kaya-Kantar, G.; Sasmaz, S.; Buyukgungor, O. J. Mol. Struct. 2015, 1087, 104-112.
https://doi.org/10.1016/j.molstruc.2015.01.039

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