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

PDF CIF FILE

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.

This Abstract was viewed 1500 times |

Article PDF downloaded 701 times

Article CIF FILE downloaded 0 times

How to Cite

(1)

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.

Links for Article

Crossref - Scopus - Google - European PMC

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

Supporting Agencies

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Downloads

Metrics