Synthesis of 5-substituted-3-methylsulfanyl-1-(2,4-dinitro phenyl)- 1H-pyrazole-4-carboxylic Acid Ethyl Esters as New Analgesic and  Anti-inflammatory Agents

P.D. Gokulan; Jayakar B.

doi:10.37285/ijddd.1.4.9

Articles

Vol. 1 No. 4 (2010): October-December 2010

Synthesis of 5-substituted-3-methylsulfanyl-1-(2,4-dinitro phenyl)- 1H-pyrazole-4-carboxylic Acid Ethyl Esters as New Analgesic and Anti-inflammatory Agents

P.D. Gokulan^▸^▾
Jayakar B.^▸^▾

Requires Subscription or Fee pdf (INR 2000)

DOI: https://doi.org/10.37285/ijddd.1.4.9
Submitted: November 25, 2024
Published: 2024-11-28

Abstract

A new series of 5-substituted-3-methylsulfanyl-1-(2,4-dinitro phenyl)-1H-pyrazole-4-carboxylic acid ethyl esters were synthesized by reacting the amino group of 5-amino-3-methylsulfanyl-1-(2,4-dinitro phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester with acid anhydrides, acid chlorides and phenyl dithiocarbamates. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic behaviour. The compound 5-benzoylamino-3-methylsulfanyl-1-(2,4-dinitro phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (3c) emerged as the active compound and exhibiting imperative analgesic and anti-inflammatory activity. Interestingly the test compounds showed only mild ulcerogenic potential when compared to indomethacin

References

[1] Van, R.J.; Botting, R.M. Inflamm. Res. 1995, 44, 1.
[2] Van, R.J.; Trummlitz, G.; Pairet, M. Curr. Med. Chem. 2000, 7, 1145.
[3] Van, R.J. Nature: New Biology 1971, 231, 232.
[4] Juby, P.F. In: Antiinflammatory Agents Scerrer RA, Whitehouse MW (Eds.), vol. I, Academic Press, New York, 1984, pp. 91-127.
[5] Daidone, G.; Plesciam, S.; Raffa, D.; Bajardi, M.L.; Matera, M.; Caruso, A.; Leone, M.G. Farmaco. 1990, 45, 391.
[6] Daidone, G.; Maggio, B.; Raffa, D.; Plescia, S.; Bajardi,
M. L.; Caruso, A.; Cutuli, V.M.C. Eur. J. Med. Chem. 1994, 29, 707.
[7] Diana, P.; Carbone, A.; Barraja, P.; Martorana, A.; Gia, O.; DallaVia, L.; Bioorg. Med. Chem. Lett. 2007, 17, 6134.
[8] Naito, H.; Ohsuki, S.; Sugimori, M.; Atsumi, R.; Minami, M.; Nakamura, Y.; Ishii, M.; Hirotani, K.; Kumazawa, E.; Ejima, A. Chem. Pharm. Bull. . 2002, 50, 453.
[9] Menozzi, G.; Mosti, L.; Bruno, O.; Lo Presti, E.; Musiu, C.; Longu, S.; La Colla, P.; Filippelli, W.; Falcone, G.; Piucci, B. Farmaco. 1999, 54, 416.
[10] Jorand-Lebrun, C.; Brondyk, B.; Lin, J.; Magar, S.; Murray, R.; Reddy, A.; Shroff, H.; Wands, G.; Weiser, W.; Xu, Q.; McKenna, S.; Brugger, N. Bioorg. Med. Chem. Lett. 2007, 17, 2080.
[11] Park, H.J.; Lee, K.; Park, S.J.; Ahn, B.; Lee, J.C.; Cho, H.; Lee, K.I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[12] Sakya, S.M.; Hou, X.; Minich, M.L.; Rast, B.; Shavnya, A.; DeMello, K.M.; Cheng, H.; Li, J.; Jaynes, B.H.; Mann, D.W.; Petras, C.F.; Seibel, S.B.; Haven, M.L. Bioorg. Med. Chem. Lett. 2007, 17, 1067.
[13] Smith, R.A.; Fathi, Z.; Brown, S.E.; Choi, S.; Fan, J.; Jenkins, S.; Kluender, H.C.; Konkar, A.; Lavoie, R.; Mays, R.; Natoli, J.; O'Connor, S.J.; Ortiz, A.A.;Podlogar, B.; Taing, C.; Tomlinson, S.; Tritto, T.; Zhang, Z. Bioorg. Med. Chem. Lett. 2007, 17, 673.
[14] Menozzi, G.; Mosti, L.; Schenone, P.; Donnoli, D.; Schiariti, F.; Marmo, E. Farmaco. 1990, 45, 167.
[15] Srivastava, B.K.; Soni, R.; Patel, J.Z.; Joharapurkar, A.; Sadhwani, N.; Kshirsagar, S.; Mishra, B.; Takale, V.; Gupta, S.; Pandya, P.; Kapadnis, P.; Solanki, M.; Patel, H.; Mitra, P.; Jain, M.R.; Patel, P.R. Bioorg. Med. Chem. Lett. 2009, 19, 2546.
[16] Farag, A.M.; Mayhoub, A.S.; Barakat, S.E.; Bayomi, A.H. Bioorg. Med. Chem. 2008, 16, 4569.
[17] Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J. J. Med. Chem. 1997, 40, 1347.
[18] Eaton, M. J. Rehabil. Res. Dev. 2003, 40, 41.
[19] Kulkarni, S.K. Life Sciences 1980, 27, 185.
[20] Amour, R.E., Smith, D.L. J. Pharm. Exp. Therap. 1941, 72, 74.
[21] Winter, C.A.; Risely, E.A.; Nuss, G.W. Exp. Biol. Med. 1962, 111, 544.
[22] Goyal, R.K.; Chakrabarti, A.; Sanyal, A.K. Planta Medica 1985, 29, 85.
[23] Shay, M.; Komarov, S.A.; Fels, D.; Meranze, D.; Grunstein,; Siplet, H. Gastroenterol. 1945, 5, 43.
[24] Ganguly, A.K.; Bhatnagar, O.P. Can. J. Physilo. Pharmacol. 1973, 51, 748.

Keywords

Pyrazole derivatives
Structure activity relationship
Analgesic
Anti-inflammatory activity

How to Cite

Gokulan, P., & B., J. (2024). Synthesis of 5-substituted-3-methylsulfanyl-1-(2,4-dinitro phenyl)- 1H-pyrazole-4-carboxylic Acid Ethyl Esters as New Analgesic and Anti-inflammatory Agents . International Journal of Drug Design and Discovery, 1(4), 345–351. https://doi.org/10.37285/ijddd.1.4.9

Similar Articles

Amit Semwal, Amit Nigam, D.C.P Singh, Synthesis, Characterization and Biological Activity of Novel N-p-methylbenzoyl-N’ substituted thiourea , International Journal of Drug Design and Discovery: Vol. 2 No. 4 (2011): October-December 2011
Arvind Semwal, Perumal Yogeeswari, Jegadeesan Vaigunda Ragavendran, Sriram Dharmarajan, James Stables, Discovery of Isatinimino Derivatives as New Leads for Neuropathic Pain Treatment: An Isomeric Modification Approach , International Journal of Drug Design and Discovery: Vol. 1 No. 2 (2010): April– June 2010
Periyasamy Selvam, Julie M. Breitenbach, Katherine Z. Borysko, John C. Drach, Synthesis, Antiviral Activity, and Cytotoxicity of some Novel 2-Phenyl-3-Disubstituted Quinazolin-4(3h)-Ones , International Journal of Drug Design and Discovery: Vol. 1 No. 2 (2010): April– June 2010
Rahul B Shete, Rishikesh V Antre, Rajesh J Oswal, Sandip S Kshirsagar, Sampada S Jangam, Hemlata M Nimje, New 4-(substituted)-pyrazolone. Part 1: Microwave-assisted synthesis and antibacterial activity of novel 4-substituted azetidinone derivatives of pyrazolone , International Journal of Drug Design and Discovery: Vol. 2 No. 4 (2011): October-December 2011
Antre Rishikesh Vilas, Cendil Kumar A, Goli Divakar, Andhale Ganesh Sakharam, Jomon Joseph , Structure, Shape, Ms Spectral Data and Biological Activities of Fullerenes , International Journal of Drug Design and Discovery: Vol. 2 No. 2 (2011): April – June 2011
Rajendra D. Dighe, Mahendra R. Shiradkar, Sheetal S. Rohom, Prashant D. Dighe, Sanjay R. Chaudhari, Microwave Assisted Synthesis and Evaluation of Thiazole Derivatives as M. tuberculosis and Antimicrobial Activity , International Journal of Drug Design and Discovery: Vol. 2 No. 2 (2011): April – June 2011
Navin B. Patel, Faiyazalam M. Shaikh, Virendra N. Patel, Hemant R. Patel, Jaymin C. Patel, New Thiazolidinyl Quinazolinones and their Microbial Activity Studies , International Journal of Drug Design and Discovery: Vol. 1 No. 3 (2010): July–September 2010
Lingappa Mallesha, Kikkeri N. Mohana, Synthesis and in vitro Biological Activity of Organic Charge-transfer Complexes of lansoprazole, fluconazole, gabapentin and gabalactum with Chloranilic and Picric Acids , International Journal of Drug Design and Discovery: Vol. 1 No. 2 (2010): April– June 2010
M.S Bhatia, K. B. Ingale, P. B. Choudhari, B. E. Zarekar, N.M. Bhatia, A.S. Sherikar, 3D QSAR: Exploring Influence of Parameters of Pyrazoline Analogues on Resistant Strains of Staphylococcus aureus , International Journal of Drug Design and Discovery: Vol. 1 No. 1 (2010): January-March 2010
Esra Tatar, İlkay Küçükgüzel, Ş.Güniz Küçükgüze, Feyza Yılmaz-Demircan, Erik De Clercq, Graciela Andrei, Robert Snoeck, Christophe Pannecouque, Fikrettin Şahin, Ömer Faruk Bayrak, Synthesis, Anti-Tuberculosis and Antiviral Activity of Novel 2-isonicotinoylhydrazono-5-arylidene-4-thiazolidinones , International Journal of Drug Design and Discovery: Vol. 1 No. 1 (2010): January-March 2010

<< < 1 2 3 4 5 6 7 8 > >>

You may also start an advanced similarity search for this article.

[1] [1] Van, R.J.; Botting, R.M. Inflamm. Res. 1995, 44, 1.

[2] [2] Van, R.J.; Trummlitz, G.; Pairet, M. Curr. Med. Chem. 2000, 7, 1145.

[3] [3] Van, R.J. Nature: New Biology 1971, 231, 232.

[4] [4] Juby, P.F. In: Antiinflammatory Agents Scerrer RA, Whitehouse MW (Eds.), vol. I, Academic Press, New York, 1984, pp. 91-127.

[5] [5] Daidone, G.; Plesciam, S.; Raffa, D.; Bajardi, M.L.; Matera, M.; Caruso, A.; Leone, M.G. Farmaco. 1990, 45, 391.

[6] [6] Daidone, G.; Maggio, B.; Raffa, D.; Plescia, S.; Bajardi,

[7] M. L.; Caruso, A.; Cutuli, V.M.C. Eur. J. Med. Chem. 1994, 29, 707.

[8] [7] Diana, P.; Carbone, A.; Barraja, P.; Martorana, A.; Gia, O.; DallaVia, L.; Bioorg. Med. Chem. Lett. 2007, 17, 6134.

[9] [8] Naito, H.; Ohsuki, S.; Sugimori, M.; Atsumi, R.; Minami, M.; Nakamura, Y.; Ishii, M.; Hirotani, K.; Kumazawa, E.; Ejima, A. Chem. Pharm. Bull. . 2002, 50, 453.

[10] [9] Menozzi, G.; Mosti, L.; Bruno, O.; Lo Presti, E.; Musiu, C.; Longu, S.; La Colla, P.; Filippelli, W.; Falcone, G.; Piucci, B. Farmaco. 1999, 54, 416.

[11] [10] Jorand-Lebrun, C.; Brondyk, B.; Lin, J.; Magar, S.; Murray, R.; Reddy, A.; Shroff, H.; Wands, G.; Weiser, W.; Xu, Q.; McKenna, S.; Brugger, N. Bioorg. Med. Chem. Lett. 2007, 17, 2080.

[12] [11] Park, H.J.; Lee, K.; Park, S.J.; Ahn, B.; Lee, J.C.; Cho, H.; Lee, K.I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.

[13] [12] Sakya, S.M.; Hou, X.; Minich, M.L.; Rast, B.; Shavnya, A.; DeMello, K.M.; Cheng, H.; Li, J.; Jaynes, B.H.; Mann, D.W.; Petras, C.F.; Seibel, S.B.; Haven, M.L. Bioorg. Med. Chem. Lett. 2007, 17, 1067.

[14] [13] Smith, R.A.; Fathi, Z.; Brown, S.E.; Choi, S.; Fan, J.; Jenkins, S.; Kluender, H.C.; Konkar, A.; Lavoie, R.; Mays, R.; Natoli, J.; O'Connor, S.J.; Ortiz, A.A.;Podlogar, B.; Taing, C.; Tomlinson, S.; Tritto, T.; Zhang, Z. Bioorg. Med. Chem. Lett. 2007, 17, 673.

[15] [14] Menozzi, G.; Mosti, L.; Schenone, P.; Donnoli, D.; Schiariti, F.; Marmo, E. Farmaco. 1990, 45, 167.

[16] [15] Srivastava, B.K.; Soni, R.; Patel, J.Z.; Joharapurkar, A.; Sadhwani, N.; Kshirsagar, S.; Mishra, B.; Takale, V.; Gupta, S.; Pandya, P.; Kapadnis, P.; Solanki, M.; Patel, H.; Mitra, P.; Jain, M.R.; Patel, P.R. Bioorg. Med. Chem. Lett. 2009, 19, 2546.

[17] [16] Farag, A.M.; Mayhoub, A.S.; Barakat, S.E.; Bayomi, A.H. Bioorg. Med. Chem. 2008, 16, 4569.

[18] [17] Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J. J. Med. Chem. 1997, 40, 1347.

[19] [18] Eaton, M. J. Rehabil. Res. Dev. 2003, 40, 41.

[20] [19] Kulkarni, S.K. Life Sciences 1980, 27, 185.

[21] [20] Amour, R.E., Smith, D.L. J. Pharm. Exp. Therap. 1941, 72, 74.

[22] [21] Winter, C.A.; Risely, E.A.; Nuss, G.W. Exp. Biol. Med. 1962, 111, 544.

[23] [22] Goyal, R.K.; Chakrabarti, A.; Sanyal, A.K. Planta Medica 1985, 29, 85.

[24] [23] Shay, M.; Komarov, S.A.; Fels, D.; Meranze, D.; Grunstein,; Siplet, H. Gastroenterol. 1945, 5, 43.

[25] [24] Ganguly, A.K.; Bhatnagar, O.P. Can. J. Physilo. Pharmacol. 1973, 51, 748.