

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,*)



(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.
Announcements
One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.8.1.1-7.1512
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Piotr Stępnicki, Olga Wronikowska-Denysiuk, Agata Zięba, Katarzyna M. Targowska-Duda, Agata Bartyzel, Martyna Z. Wróbel, Tomasz M. Wróbel, Klaudia Szałaj, Andrzej Chodkowski, Karolina Mirecka, Barbara Budzyńska, Emilia Fornal, Jadwiga Turło, Marián Castro, Agnieszka A. Kaczor
Novel multi-target ligands of dopamine and serotonin receptors for the treatment of schizophrenia based on indazole and piperazine scaffolds–synthesis, biological activity, and structural evaluation
Journal of Enzyme Inhibition and Medicinal Chemistry 38(1), , 2023
DOI: 10.1080/14756366.2023.2209828

[2]. Piotr Stępnicki, Katarzyna M. Targowska-Duda, Antón L. Martínez, Agata Zięba, Olga Wronikowska-Denysiuk, Martyna Z. Wróbel, Agata Bartyzel, Alicja Trzpil, Tomasz M. Wróbel, Andrzej Chodkowski, Karolina Mirecka, Tadeusz Karcz, Katarzyna Szczepańska, Maria I. Loza, Barbara Budzyńska, Jadwiga Turło, Jadwiga Handzlik, Emilia Fornal, Ewa Poleszak, Marián Castro, Agnieszka A. Kaczor
Discovery of novel arylpiperazine-based DA/5-HT modulators as potential antipsychotic agents – Design, synthesis, structural studies and pharmacological profiling
European Journal of Medicinal Chemistry 252, 115285, 2023
DOI: 10.1016/j.ejmech.2023.115285

[3]. Li-Yan Zeng, Fubiao Yang, Kaixuan Chen, Yunong Zeng, Zhenzhou Jiang, Shuwen Liu, Baomin Xi
The one-pot synthesis of butyl-1H-indol-3-alkylcarboxylic acid derivatives in ionic liquid as potent dual-acting agent for management of BPH
European Journal of Medicinal Chemistry 205, 112616, 2020
DOI: 10.1016/j.ejmech.2020.112616

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
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

















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 - 2023 • 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 2010-2023 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.