

QSAR rationales for the 1,2-diarylcyclopentenes as prostaglandin EP1 receptor antagonists: Potentially useful in the treatment of inflammatory pain
Brij Kishore Sharma (1,*)



(1) Department of Chemistry, Shri Kalyan Government College, Sikar, IN-332001, India
(2) Department of Chemistry, Shri Kalyan Government College, Sikar, IN-332001, India
(3) Department of Chemistry, Shri Kalyan Government College, Sikar, IN-332001, India
(*) Corresponding Author
Received: 06 Jul 2010 | Revised: 28 Aug 2010 | Accepted: 01 Sep 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
The EP1 receptor inhibitory activity of 1,2-diarylcyclopentene derivatives have been quantitatively analyzed in terms of Dragon descriptors. The derived QSAR models have provided rationales to explain the EP1 receptor inhibitory activity of 1,2-diarylcyclopentene derivatives. The 2D-autocorrelation descriptors (MATS4e, MATS5e, MATS7v, GATS5e and GATS7v) have highlighted the role of atomic properties in respective lags of autocorrelations to explain the biological actions of 1,2-diarylcyclopentene analogues. Presence of fluorine atom (nF) and smaller distance between N and O atoms (T(N..O)) in molecular structures, in addition to Kier-Hall electrotopological states (Ss) have also shown prevalence to optimize the EP1 receptor inhibitory activity. Partial least square analysis has confirmed the dominance of information content of the combinatorial protocol in multiple linear regression identified descriptors. Applicability domain analysis revealed that the suggested model matches the high quality parameters with good fitting power and capability of assessing external data. All the compounds are within the applicability domain of the proposed model and were evaluated correctly.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.1.4.325-334.195
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Tawassl Tajelsir Hassan Hajalsiddig, Ahmed Elsadig Mohammed Saeed
QSAR and molecular docking studies on 4-quinoline carboxylic acid derivatives as inhibition of vesicular stomatitis virus replication
European Journal of Chemistry 10(1), 45, 2019
DOI: 10.5155/eurjchem.10.1.45-51.1795

[2]. Mukesh C. Sharma, Smita Sharma, Shivangi Sharma
Computational study of diarylcyclopentene derivatives as selective prostaglandin EP1 receptor antagonist: QSAR approach
Network Modeling Analysis in Health Informatics and Bioinformatics 5(1), , 2016
DOI: 10.1007/s13721-016-0120-y

References
[1]. Murakami, M.; Nakatani, Y.; Tanioka, T.; Kudo, I. Prostaglandins Other Lipid Mediat. 2002, 68-69, 383-399.
doi:10.1016/S0090-6980(02)00043-6
[2]. Claveau, D.; Sirinyan, M.; Guay, J.; Gordon, R.; Chan, C-C.; Bureau, Y.; Riendeau, D.; Mancini, J. A. J. Immunol. 2003, 170, 4738-4744.
[3]. Trebino, C. E.; Stock, J. L.; Gibbons, C. P.; Naiman, B. M.; Wachtmann, T. S.; Umland, J. P.; Pandher, K.; Lapointe, J-M.; Saha, S.; Roach, M. L.; Carter, D.; Thomas, N. A.; Durtschi, B. A.; McNeish, J. D.; Hambor, J. E.; Jakobsson, P-J.; Carty, T. J.; Perez J. R.; Audoly, L. P. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9044-9049.
doi:10.1073/pnas.1332766100
PMid:12835414 PMCid:166435
[4]. Kamei, D.; Yamakawa, K.; Takegoshi, Y.; Mikami-Nakanishi, M.; Nakatani, Y.; Oh-ishi, S.; Yasui, H.; Azuma, Y.; Hirasawa, N.; Ohuchi, K.; Kawaguchi, H.; Ishikawa, Y.; Ishii, T.; Uematsu, S.; Akira, S.; Murakami, M.; Kudo, I. J. Biol. Chem. 2004, 279, 33684-33695.
doi:10.1074/jbc.M400199200
PMid:15140897
[5]. Mabuchi, T.; Kojima, H.; Abe, T.; Takagi, K.; Sakurai, M.; Ohmiya, Y.; Uematsu, S.; Akira, S.; Watanabe, K.; Ito, S. Neuroreport 2004, 15, 1395-1398.
doi:10.1097/01.wnr.0000129372.89000.31
PMid:15194860
[6]. Camu, F.; Shi, L.; Vanlersberghe, C. Drugs 2003, 63(suppl. 1), 1-7.
doi:10.2165/00003495-200363001-00002
PMid:14506906
[7]. Bianchi, M.; Broggini, M. Drugs 2003, 63(suppl. 1), 37-46.
doi:10.2165/00003495-200363001-00006
PMid:14506910
[8]. Jeger, R. V.; Greenberg, J. D.; Ramanathan, K.; Farkouh, M. E. Exp. Rev. Clin. Immunol. 2005, 1, 37-45.
doi:10.1586/1744666X.1.1.37
PMid:20477653
[9]. Lee, Y.; Rodriguez, C.; Dionne, R. A. Curr. Pharm. Des. 2005, 11, 1737-1755.
doi:10.2174/1381612053764896
PMid:15892672
[10]. Akarca, U. S. Curr. Pharm. Des. 2005, 11, 1779-1793.
doi:10.2174/1381612053764904
PMid:15892675
[11]. Sheen, C. L.; MacDonald, T. M. Exp. Opin. Pharmacother. 2002, 3, 265-269.
doi:10.1517/14656566.3.3.265
PMid:11866677
[12]. Hawkey, C. J.; Jackson, L.; Harper, S. E.; Simon, T. J.; Mortensen, E.; Lines, C. R. Aliment. Pharmacol. Ther. 2001, 15, 1-9.
doi:10.1046/j.1365-2036.2001.00894.x
[13]. Bombardier, C.; Laine, L.; Reicin, A.; Shapiro, D.; Burgos-Vargas, R.; Davis, B.; Day, R.; Bosi Ferraz, M.; Hawkey, C. J.; Hochberg, M. C.; Kvien T. K.; Schnitzer, T. J.; VIGOR study group. N. Eng. J. Med. 2000, 343, 1520-1528.
doi:10.1056/NEJM200011233432103
PMid:11087881
[14]. Silverstein, F. E.; Faich, G.; Goldstein, J. L.; Simon, L. S.; Pincus, T.; Whelton, A.; Makuch, R.; Eisen, G.; Agrawal, N. M.; Stenson, W. F.; Burr, A. M.; Zhao, W. W.; Kent, J. D.; Lefkowith, J. B.; Verburg, K. M.; Geis, G. S. J. Am. Med. Assoc. 2000, 284, 1247-1255.
doi:10.1001/jama.284.10.1247
PMid:10979111
[15]. Merck & Co. Press Release; 30 September 2004. http://www.merck.com.
[16]. Mukherjee, D.; Nissen, S. E.; Topol, E. J. J. Am. Med. Assoc. 2001, 286, 954-959.
doi:10.1001/jama.286.8.954
PMid:11509060
[17]. Mamdani, M.; Juurlink, D. N.; Lee, D. S.; Rochon, P. A.; Kopp, A.; Naglie, G.; Austin, P. C.; Laupacis, A.; Stukel, T. A. Lancet 2004, 363, 1751-1756.
doi:10.1016/S0140-6736(04)16299-5
[18]. Scheen, A. J. Rev. Med. Liege 2004, 59, 565-569.
PMid:15623076
[19]. Bresalier, R. S.; Sandier, R. S.; Quan, H.; Bolognese, J. A.; Oxenius, B.; Horgan, K.; Lines, C.; Riddell, R.; Morton, D.; Lanas, A.; Konstam, M. A.; Baron, J. A. N. Engl. J. Med. 2005, 352, 1092-1102.
doi:10.1056/NEJMoa050493
PMid:15713943
[20]. Solomon, S. D.; McMurray, J. J. V.; Pfeffer, M. A.; Wittes, J.; Fowler, R.; Finn, P.; Anderson, W. F.; Zauber, A.; Hawk E.; Bertagnolli, M. N. Engl. J. Med. 2005, 352, 1071-1080.
doi:10.1056/NEJMoa050405
PMid:15713944
[21]. Fitzgerald, G. A. N. Engl. J. Med. 2004, 351, 1709-1711.
doi:10.1056/NEJMp048288
PMid:15470192
[22]. Lagakos, S. W. N. Engl. J. Med. 2006, 355, 113-117.
doi:10.1056/NEJMp068137
PMid:16801354
[23]. Meagher, E. A. Curr. Pharm. Des. 2004, 10, 603-611.
doi:10.2174/1381612043453153
PMid:14965323
[24]. Coleman, R. A.; Smith, W. L.; Narumiya, S. Pharmacol. Rev. 1994, 46, 205-229.
PMid:7938166
[25]. Breyer, R. M.; Bagdassarian, C. K.; Myers, S. A.; Breyer, M. D. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 661-690.
doi:10.1146/annurev.pharmtox.41.1.661
PMid:11264472
[26]. Narumiya, S.; Sugimoto, Y.; Ushikubi, F. Physiol. Rev. 1999, 79, 1193-1226.
PMid:10508233
[27]. Coleman, R. A.; Kennedy, I.; Humphrey, P. P. A.; Bunce, K.; Lumley, P. Comprehensive Medicinal Chemistry, 3rd volume, Pergamon: Oxford, UK, 1990.
[28]. Hata, A. N.; Breyer, R. M. Pharmacol. Ther. 2004, 103, 147-166.
doi:10.1016/j.pharmthera.2004.06.003
[29]. Ungrin, M. D.; Carrière, M-C.; Denis, D.; Lamontagne, S.; Sawyer, N.; Stocco, R.; Tremblay, N.; Metters, K. M.; Abramovitz, M. Mol. Pharmacol. 2001, 59, 1446–1455.
PMid:11353805
[30]. Hallinan, E.; Hagen, T.; Jusa, R.; Tsymbalov, S.; Rao, S.; van Hoeck, J-P.; Rafferty, M.; Stapelfeld, A.; Savage, M.; Reichman, M. J. Med. Chem. 1993, 36, 3293-3299.
doi:10.1021/jm00074a010
PMid:7901416
[31]. Hallinan, E.; Stapelfeld, A.; Savage, M.; Reichman, M. Bioorg. Med. Chem. Lett. 1994, 4, 509-514.
doi:10.1016/0960-894X(94)80027-8
[32]. Lanthorn, T.; Bianchi, R.; Perkins, W. Drug Dev. Res. 1995, 34, 35–38.
doi:10.1002/ddr.430340106
[33]. Novel EP1 receptor antagonists. Expert Opin. Ther. Patents 2004, 14, 435-438.
[34]. Breault, G.A. WO9700863A1, 1997.
[35]. Watanabe, K.; Kawamori, T.; Nakatsugi, S.; Ohta, T.; Ohuchida, S.; Yamamoto, H.; Maruyama, T.; Kondo, K.; Narumiya, S.; Sugimura, T.; Wakabayashi, K. Cancer Lett. 2000, 156, 57-61.
doi:10.1016/S0304-3835(00)00440-7
[36]. Ducharme, Y.; Blouin, M.; Carrière, M. C.; Chateauneuf, A.; Côte, B.; Denis, D.; Frenette, R.; Greig, G.; Kargman, S.; Lamontagne, S.; Martins, E.; Nantel, F.; O’Neill, G.; Sawyer, N.; Metters, K. M.; Friesen, R. W. Bioorg. Med. Chem. Lett. 2005, 15, 1155-1160.
doi:10.1016/j.bmcl.2004.12.005
[37]. Minami, T.; Nakano, H.; Kobayashi, T.; Sugimoto, Y.; Ushikubi, F.; Ichikawa, A.; Narumiya, S.; Ito, S. Br. J. Pharmacol. 2001, 133, 438-444.
doi:10.1038/sj.bjp.0704092
PMid:11375261 PMCid:1572799
[38]. Mebane, H.; Turnbach, M. E.; Randich, A. J. Pain 2003, 4, 392-399.
PMid:11160156 PMCid:199184
[39]. Stock, J. L.; Shinjo, K.; Burkhardt, J.; Roach, M.; Taniguchi, K.; Ishikawa, T.; Kim, H-S.; Flannery, P. J.; Coffman, T. M.; McNeish, J. D.; Audoly, L. P. J. Clin. Invest. 2001, 107, 325-331.
doi:10.1172/JCI6749
[40]. Omote, K.; Kawamata, T.; Nakayama, Y.; Kawamata, M.; Hazama, K.; Namiki, A. Anesth. Analg. 2001, 92, 233-238.
doi:10.1097/00000539-200101000-00045
[41]. Omote, K.; Yamamoto, H.; Kawamata, T.; Nakayama, Y.; Namiki, A. Anesth. Analg. 2002, 95, 1708-1712.
doi:10.1097/00000539-200212000-00044
[42]. Kawahara, H.; Sakamoto, T.; Takeda, S.; Onodera, H.; Imaki, J.; Ogawa, R. Anesth. Analg. 2001, 93, 1012-1017.
doi:10.1097/00000539-200110000-00043
[43]. Giblin, G. M. P.; Bit, R. A.; Brown, S. H.; Chaignot, H. M.; Chowdhury, A.; Chessell, I. P.; Clayton, N. M.; Coleman, T.; Hall, A.; Hammond, B.; Hurst, D. N.; Michel, A. D.; Naylor, A.; Novelli, R.; Scoccitti, T.; Spalding, D.; Tang, S. P.; Wilson, A. W.; Wilson, R. Bioorg. Med. Chem. Lett. 2007, 17, 385-389.
doi:10.1016/j.bmcl.2006.10.041
[44]. SYSTAT, Version 7.0; SPSS Inc., 444 North Michigan Avenue, Chicago, IL, 60611.
[45]. ChemDraw Ultra 6.0 and Chem3D Ultra, Cambridge Soft Corporation, Cambridge, USA. http://www.cambridgesoft.com
[46]. Dragon software (version 1.11-2001) by Todeschini R.; Consonni V. Milano, Italy. http://www.talete.mi.it/dragon.htm
[47]. Prabhakar, Y. S. QSAR Comb. Sci. 2003, 22, 583-595.
doi:10.1002/qsar.200330814
[48]. Wold, S. Technometrics 1978, 20, 397-405.
doi:10.2307/1267639
[49]. Kettaneh, N.; Berglund, A.; Wold, S. Comput. Stat. Data Anal. 2005, 48, 69-85.
doi:10.1016/j.csda.2003.11.027
[50]. Stahle, L.; Wold, S. Biomedical Research, Progress in Medicinal Chemistry, vol. 25, Elsevier Science Publishers, BV, 1998.
[51]. Sharma, B. K.; Pilania, P.; Singh, P.; Sharma, S.; Prabhakar, Y. S. Cent. Eur. J. Chem. 2009, 7, 909-922.
doi:10.2478/s11532-009-0073-4
PMid:18825552
[52]. Sharma, B. K.; Pilania, P.; Singh, P. J. Enz. Inhib. Med. Chem. 2009, 24, 607-615.
doi:10.1080/14756360802318878
PMid:19548781
[53]. Sharma, S.; Sharma, B. K.; Pilania, P.; Singh, P.; Prabhakar, Y. S. J. Enz. Inhib. Med. Chem. 2009, 24, 1024-1033.
doi:10.1080/14756360802608054
PMid:20373219
[54]. Sharma, B. K.; Pilania, P.; Singh, P.; Prabhakar, Y. S. SAR QSAR Environ. Res. 2010, 21, 169-185.
doi:10.1080/10629360903570545
PMid:19657719
[55]. Sharma, B. K.; Pilania, P.; Sarbhai, K.; Singh, P.; Prabhakar, Y. S. Mol. Divers. 2010, 14, 371-384.
doi:10.1007/s11030-009-9181-5
[56]. Akaike, H. Second international symposium on information theory, Akademiai Kiado, Budapest, 1973.
[57]. Akaike, H. IEEE Trans. Automat. Contr. 1974, AC-19, 716-723.
doi:10.1109/TAC.1974.1100705
[58]. Kubinyi, H. Quant. Struct.-Act. Relat. 1994, 13, 285-294.
[59]. Kubinyi, H. Quant. Struct.-Act. Relat. 1994, 13, 393-401.
PMid:9435904
[60]. Friedman, J. Technical report no. 102. Laboratory for computational statistics. Stanford University, Stanford, 1990.
[61]. So, S. -S.; Karplus, M. J. Med. Chem. 1997, 40, 4347-4359.
doi:10.1021/jm970487v
[62]. Prabhakar, Y. S.; Solomon, V. R.; Rawal, R. K.; Gupta, M. K.; Katti, S. B. QSAR Comb. Sci. 2004, 23, 234-244.
doi:10.1002/qsar.200330854
[63]. Gramatica, P. QSAR Comb. Sci. 2007, 26, 694-701.
doi:10.1002/qsar.200610151
[64]. Golbraikh, A.; Tropsha, A. J. Mol. Graph. Model. 2002, 20, 269-276.
doi:10.1016/S1093-3263(01)00123-1
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.1.4.325-334.195

















European Journal of Chemistry 2010, 1(4), 325-334 | doi: https://doi.org/10.5155/eurjchem.1.4.325-334.195 | 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.