European Journal of Chemistry 2017, 8(1), 1-7 | doi: https://doi.org/10.5155/eurjchem.8.1.1-7.1512 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Zarife Sibel Şahin (1,*) , Mine Yarım (2) , Meriç Köksal (3)

(1) Sinop University, Faculty of Engineering and Architectures, Department of Energy Systems Engineering, 57000, Sinop, Turkey
(2) Yeditepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34755, Kayışdağı, İstanbul, Turkey
(3) Yeditepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34755, Kayışdağı, İstanbul, Turkey
(*) Corresponding Author

Received: 01 Dec 2016 | Revised: 22 Dec 2016 | Accepted: 25 Dec 2016 | Published: 31 Mar 2017 | Issue Date: March 2017

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.


Keywords


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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.1.1-7.1512

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 653 times | PDF Article downloaded 195 times


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 information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Şahin, Z.; Yarım, M.; Köksal, M. Eur. J. Chem. 2017, 8(1), 1-7. doi:10.5155/eurjchem.8.1.1-7.1512
Şahin, Z.; 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), 1-7. doi:10.5155/eurjchem.8.1.1-7.1512
Şahin, Z., Yarım, M., & Köksal, M. (2017). Density functional computational and X-ray studies on pharmaceutical compound 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole. European Journal of Chemistry, 8(1), 1-7. doi:10.5155/eurjchem.8.1.1-7.1512
Şahin, Zarife, Mine Yarım, & Meriç Köksal. "Density functional computational and X-ray studies on pharmaceutical compound 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole." European Journal of Chemistry [Online], 8.1 (2017): 1-7. Web. 21 Oct. 2020
Şahin, Zarife, Yarım, Mine, AND Köksal, Meriç. "Density functional computational and X-ray studies on pharmaceutical compound 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole" European Journal of Chemistry [Online], Volume 8 Number 1 (31 March 2017)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


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

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2017, 8(1), 1-7 | doi: https://doi.org/10.5155/eurjchem.8.1.1-7.1512 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.