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.^▸^▾

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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

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

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[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.