A series of sulpha/substituted derivatives of phenyl azo-1,2-diazole have been synthesized and tested as an anti-inflammatory and anti-bacterial activity in mature albino rats hind paw by taking Diclofenac sodium as standard. N1-(4-hydroxy benzoyl)-3-methyl-5-phenyl-4(N-4-chlorophenylazo)-1,2-diazole is synthesized by a two-step process. In the first step, synthesis of N1-4-chlorophenyl hydrazono-1-methyl-3-phenyl propane-1,3-dione by the reciprocal action of 1-methyl-5-phenylpropane-1,3-dione and diazonium salt solution of phenyl-chloride interacts with 4-hydroxybenzoic acid hydrazide to form the final compound. These diazoles, the heterocyclic compounds which contained electron withdrawing groups, were screened for analgesic activity by acetic acid induced writing method, and for anti-inflammatory activity carried on carrageenan-induced paw edema. The synthesized substituted Chlorophenylazo-1,2-diazole nucleus exhibited significant anti-bacterial, anti-cancer, anti-inflammatory activity, muscle relaxing and moderate activity in anti-proliferative studies.
Eicher, T., Hauptmann, S. and Speicher, A. (2003) The Chemistry of Heterocycles: Structure, Reactions Synthesis and Applications. 2nd Edition, Wiley-VCH, Weinheim. https://doi.org/10.1002/352760183X
[3]
Schmidt, A. and Dreger, A. (2011) Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities and Synthesis. Current Organic Chemistry, 15, 1423 -1463. https://doi.org/10.2174/138527211795378263
[4]
Rybak, L.P., Whitworth, C. and Scott, V. (1991) Comperative Acute Ototoxicity of Loop Diuretic Compounds. European Archives of Oto-Rhino-Laryngology, 248, 353-357. https://doi.org/10.1007/BF00169028
[5]
Prabhu, V.V., Kannan, N. and Guruvayoorappan, C. (2013) 1,2-Diazole Prevents Cisplatin-Induced Nephrotoxicity in Experimental Rats. Pharmacological Reports, 65, 980-990. https://doi.org/10.1016/S1734-1140(13)71079-X
[6]
Taylor, E.C. and Patel, H.H. (1992) Synthesis of Pyrazole 3,4-Dpyrimidine Analogues of the Potent Agent N-4-2-2-amino-43H-oxo-7H-pyrrolo2,3-dpyrimidin-5 -yl Ethylbenzoyl-L-glutamic Acid (LY231514). Tetrahedron, 48, 8089-8100.
https://doi.org/10.1016/S0040-4020(01)80479-8
[7]
Abdel-Rahman, A.A., Abdel-Megied, A.E., Hawata, M.A., Kasem, E.R. and Shabaan, M.T. (2007) Synthesis and Antimicrobial Evaluation of Some Chalcones and Their Derived Pyrazoles, Pyrazolines, Isoxzolines and 5,6-Dihydropyrimidine-2-(1H)-thiones. Monatshefte für Chemie—Chemical Monthly, 138, 889-897.
https://doi.org/10.1007/s00706-007-0700-8
[8]
Sharshira, E.M. and Hamada, N.M. (2011) Synthesis and in Vitro Antimicrobial Activity of Some Pyrazolyl-1-carboxamide Derivatives. Molecules, 16, 7736-7745.
https://doi.org/10.3390/molecules16097736
[9]
Rashad, A.E., Shamrokh, A.H., Hegab, M.I. and Awad, H.M. (2005) Synthesis of Some Biologically Active Pyrazoles and C-Nucleosides. Acta Chimica Slovenica, 52, 429-434.
[10]
Rashad, A.E., Hegab, M.I., Abdel-Megeid, R.E., Micky, J.A. and Abdel-Megeid, F.M. (2008) Synthesis and Antiviral Evaluation of Some New Pyrazole and Fused Pyrazolopyrimidine Derivatives. Bioorganic & Medicinal Chemistry, 16, 7102-7106.
https://doi.org/10.1016/j.bmc.2008.06.054
[11]
Bhatt, B.A., Dhar, K.L., Puri, S.C., Saxena, A.K., Shanmugavel, M. and Qazi, G.N. (2005) Synthesis and Biological Evaluation of Chalcones and Their Derived Pyrazoles as Potential Cytotoxic Agent. Bioorganic & Medicinal Chemistry Letters, 15, 3177-3180. https://doi.org/10.1016/j.bmcl.2005.03.121
[12]
Edwards, M.L., Stemerick, D.M. and Sunkara, P.S. (1990) Chalcones: A New Class of Antimitotic Agents. Journal of Medicinal Chemistry, 33, 1948-1954.
https://doi.org/10.1021/jm00169a021
[13]
Vibhute, Y.B. and Baseer, M.A. (2003) Synthesis and Activities of a New Series of Chalcones as Antibacteriasl Agents. Indian Journal of Chemistry, 42, 202-205.
[14]
Clinton, R.O., Manson, A.J., Stonner, F.W., Beyler, A.L., Potts, G.O. and Arnold, A. (1959) Steroidal [3,2-c] Pyrazoles. Journal of the American Chemical Society, 81, 1513-1514. https://doi.org/10.1021/ja01515a060
[15]
Kalirajan, R., Sivakumar, S.U., Gowramma, J.B. and Suresh, B. (2007) Synthesis and Biological Evaluation of Some Heterocyclic Derivatives Chalcones. International Journal of Chemical Sciences, 5, 73-80.
[16]
Butler, J., Forman, D.E., Abraham, W.T., Gottlieb, S.S., Loh, E., Massie, B.M., O’Connor, C.M., Rich, M.W., Stevenson, L.W., Wang, Y., Young, J.B. and Krumholz, H.M. (2004) Relationship between Heart Failure Treatment and Development of Worsening Enal Function among Hospitalized Patients. American Heart Journal, 147, 331-338. https://doi.org/10.1016/j.ahj.2003.08.012
[17]
Maccari, R., Vitale, R.M., Ottanà, R., Rocchiccioli, M., Marrazzo, A., Cardile, V., Graziano, A.C.E., Amodeo, P. and Mura, U. (2014) Structure-Activity Relationships and Molecular Modelling of New 5-Arylidene-4-Thiazolidinone Derivatives as Aldose Reductase Inhibitors and Potential Anti-Inflammatory Agents. European Journal of Medicinal Chemistry, 81, 1-14.
https://doi.org/10.1016/j.ejmech.2014.05.003
[18]
Kucheryavyi, Y.N., Kaplaushenko, A.G. and Pruhlo, E.S. (2014) Synthesis and Diuretic Activity of 2-(5-(Phenoxymethyl)-4-r1-1,2,4-Triazole-3-Ylthio) Acetic Acids and Their Salts. Problems of Pharmacy, 6, 101-104.
[19]
Murugesan, T., Manikandan, L., Suresh, K.B., Pal, M. and Saha, B.P. (2000) Evaluation of Diuretic Potential of Jussiaea suffruticosa Linn: Extract in Rats. Indian Journal of Pharmaceutical Sciences, 62, 152-156.
[20]
Patel, U., Kulkarni, M., Undale, V. and Bhosale, A. (2009) Evaluation of Diuretic Activity of Aqueous and Methanol Extracts of Lepidium sativum Garden Cress (Cruciferae) in Rats. Tropical Journal of Pharmaceutical Research, 8, 215-219.
https://doi.org/10.4314/tjpr.v8i3.44536
[21]
Singh, Y., Chaurasia, L. and Nayal, S.S. (2000) Antifungal Activity of Bicyclic Heterocyclic-1,2-Diazole. Indian Journal of Experimental Biology, 38, 516-518.
[22]
Malik, R., Pal, N., Singh, G. and Singh, C.P. (2013) Synthesis and Anti-Inflammatory Activity On Sulpha/Substituted Pyrazoles(1,2-Diazole). IOSR Journal of Pharmacy, 3, 27-30.
[23]
Saini, M.S., Singh, R., Dwivedi, J. and Kumar, A. (2012) Synthesis and Biological Activity of Some N-Benzylidene Derivatives of 2-Aryl-5-Hydroxy-7-Methyl-1,2,4-Trizolo-[1,5-a]-Pyrimidines. International Journal of Science and Nature, 3, 925-927.
[24]
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahin, F. and Gulluce, M. (2006) Synthesis and Biological Activity of 4-Thiazolidinones, Thiosemicarbazides Derived from Diflunisal Hydrazide. European Journal of Medicinal Chemistry, 41, 353-359.
https://doi.org/10.1016/j.ejmech.2005.11.005
[25]
Mukherjee, P.K., Das, J., Saha, K., Pal, M. and Saha, B.P. (1996) Diuretic Activity of Extract of the Rhizomes of Nelumbo nucifera Gaertn (Fam. Nymphaeaceae). Phytotherapy Research, 10, 424-425.
https://doi.org/10.1002/(SICI)1099-1573(199608)10:5<424::AID-PTR857>3.0.CO;2-3
[26]
Vigorita, M.G., Ottana, R., Monforte, F., Maccari, R., Trovato, A., Monforte, M.T. and Taviano, M.F. (2001) Synthesis and Anti-Inflammatory, Analgesic Activity of 3,3’-(1,2-Ethanediyl)-Bis[2-Aryl-4-Thiazolidinone] Chiral Compounds. Part 10. Bioorganic & Medicinal Chemistry Letters, 11, 2791-2794.
https://doi.org/10.1016/S0960-894X(01)00476-0
[27]
Bhatt, S., Singh, C.P. and Kumar, D. (2012) Synthesis of Novel N1-(4-Amino Benzoyl)-3-Methyl-5-Phenyl-4(N-4sulfamoylphenylazo)-1,2-Diazole. IOSR Journal of Pharmacy, 2, 60-64.
[28]
Lalit Gupta, R. and Singh, C.P. (2014) Synthesis and Anti-Inflammatory Active Sulpha/Substituted 1,2-Diazoles. International Journal of Applied Research, 4, 20-22.