全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

An Eco-Friendly Synthesis of Heterocyclic Moieties Condensed with Pyrazole System under Green Conditions and Their Biological Activity

DOI: 10.4236/gsc.2016.62008, PP. 88-100

Keywords: 4-Bromo Pyrazolone, N-Bromo Saccharine, Chitosan, Microwave Irradiation, DPPH

Full-Text   Cite this paper   Add to My Lib

Abstract:

The efficient, facile and green synthesis of 4-bromo pyrazolone by using N-bromo saccharine as valuable green reagent encouraged us to prepare some new fused heterocycles as furopyrazole, pyranopyrazole, imidazopyrazole, pyrazolothiazole, pyrazol thiazolopyrimidine, pyrazolothiazine, oxathinopyrazole, pyrazolobenzooxazine, and pyrazoloquinoxaline. The synthesis was carried out by a basic condensation of bromo pyrazolone 2 and a suitable reagent in a one-pot reaction using chitosan as a green basic catalyst. The reactions were carried out by microwave irradiation technique as a green source of energy as well as the conventional heating. The antioxidant activity of the prepared compounds was studied using 1,1-phenyl-2-picrylhydrazyl (DPPH) assay and their antibacterial activity against Gram-positive, Gram-negative bacteria and antifungal activity was evaluated.

References

[1]  Tejedor, D. and Garcia-Tellador, F. (2007) Chemo-Differentiating ABB’ Multicomponent Reactions. Privileged Building Blocks. Chemical Society Reviews, 36, 484-491.
http://dx.doi.org/10.1039/B608164A
[2]  Weber, L. (2002) Multi-Component Reactions and Evolutionary Chemistry. Drug Discovery Today, 7, 143-147.
http://dx.doi.org/10.1016/S1359-6446(02)00010-7
[3]  Hulme, C. and Gore, V. (2003) Multi-component Reactions: Emerging Chemistry in Drug Discovery from Xylocain to Crixivan. Current Medicinal Chemistry, 10, 51-80.
http://dx.doi.org/10.2174/0929867033368600
[4]  Rizk, H.F., EI-Badawi, M.A., Ibrahim, S.A. and El-Borai, M.A. (2011) Cyclization of 4,5-Diamino Pyrazole Derivatives and Their Antibacterial Activities. Chinese Journal of Chemistry, 29, 1451-1459.
http://dx.doi.org/10.1002/cjoc.201180265
[5]  Yang, B., Lu, Y., Chen, C.-J., Cui, J.-P. and Cai, M.-S. (2009) The Synthesis of 5-Amino-4-arylazo-3-methyl-1H-pyrazoles and 5-Aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines. Dyes and Pigments, 83, 144-147.
http://dx.doi.org/10.1016/j.dyepig.2008.12.011
[6]  Tsai, P.C. and Wang, I.J. (2005) Synthesis and Solvatochromic Properties of Some Disazo Dyes Derived from Pyrazolo [1,5-a]pyrimidine Derivatives. Dyes and Pigments, 64, 259-264.
http://dx.doi.org/10.1016/j.dyepig.2004.05.013
[7]  Kumar, V., Aggarwal, R., Tyagi, P. and Singh, S. (2005), Synthesis and Antibacterial Activity of Some New 1-Heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles. European Journal of Medicinal Chemistry, 40, 922-927.
http://dx.doi.org/10.1016/j.ejmech.2005.03.021
[8]  Yang, B., Lu, Y., Chen, C., Cui, J. and Cai, M. (2009) The Synthesis of 5-Amino-4-arylazo-3-methyl-1H-pyrazoles and 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines. Dyes and Pigments, 83, 144-147.
http://dx.doi.org/10.1016/j.dyepig.2008.12.011
[9]  Gudmundsson, K.S., Johns, B.A., Wang, Z., Turner, E.M., Allen, S.H., Freeman, G.A., Lesleboyd, F., Sexton, C.D., Sellseth, D.W., Moniri, K.R. and Greeh., K.L. (2005) Synthesis of Novel Substituted 2-Phenylpyrazolopyridines with Potent Activity against Herpesviruses. Bioorganic & Medicinal Chemistry, 13, 5346-5361.
http://dx.doi.org/10.1016/j.bmc.2005.05.043
[10]  Hwang, S.H., Wagner, K.M., Morisseau, C., Liu, J.-Y., Dong, H., Wecksler, A.T. and Hammock, B.D. (2011) Synthesis and Structure-Activity Relationship Studies of Urea-Containing Pyrazoles as Dual Inhibitors of Cyclooxygenase-2 and Soluble Epoxide Hydrolase. Journal of Medicinal Chemistry, 54, 3037-3050.
http://dx.doi.org/10.1021/jm2001376
[11]  Szabó, G., Fischer, J., Kis-Varga, á. and Gyires, K. (2008) New Celecoxib Derivatives as Anti-Inflammatory Agents. Journal of Medicinal Chemistry, 51, 142-147.
http://dx.doi.org/10.1021/jm070821f
[12]  Chimichi, S., Boccalini, M., Hassan, M.M., Viola, G., Dall ácqua, F. and Curini, M. (2006) Synthesis, Structural Determination and Photo-Antiproliferative Activity of New 3-Pyrazolyl or -Isoxazolyl Substituted 4-Hydroxy-2(1H)-quinolinones. Tetrahedron, 62, 90-96.
http://dx.doi.org/10.1016/j.tet.2005.09.135
[13]  Rizk, H.F., EI-Badawi, M.A., Ibrahim, S.A. and El-Borai, M.A. (2011) Synthesis of Some Novel Heterocyclic Dyes Derived from Pyrazole Derivatives. Arabian Journal of Chemistry, 4, 37-44.
http://dx.doi.org/10.1016/j.arabjc.2010.06.012
[14]  El-Borai, M.A., Rizk, H.F., Abd-Aal, M.F. and El-Deeb, I.Y. (2012) Synthesis of Pyrazolo[3,4-b]pyridines under Microwave Irradiation in Multi-Component Reactions and Their Antitumor and Antimicrobial Activities—Part 1. European Journal of Medicinal Chemistry, 48, 92-96.
http://dx.doi.org/10.1016/j.ejmech.2011.11.038
[15]  El-Borai, M.A., Rizk, H.F., Beltagy, D.M. and El-Deeb, I.Y. (2013) Microwave-Assisted Synthesis of Some New Pyrazolopyridines and Their Antioxidant, Antitumor and Antimicrobial Activities. European Journal of Medicinal Chemistry, 66, 415-422.
http://dx.doi.org/10.1016/j.ejmech.2013.04.043
[16]  El-Borai, M.A., Rizk, H.F., El-Deeb, I.Y. and Sadek, M.E. (2014) A Convenient Synthesis of a Series of Pyrazolo [3,4-D]pyrimidines as Potential Antimicrobial and Antioxidant Agents. Journal of Applied Chemistry, 3, 1526-1537.
[17]  Pridham, T.G., Lindenfelser, L.A., Shotwell, O.L., Stodola, F., Benedict, R.G., Foley, C., Jacks, P.W., Zaumeyer, W.J., Perston, W.H. and Mitchell, J.W. (1956) Phytopathology, 46, 27.
[18]  Skehan, P., Storeng, R., Scudiero, D., Monks, A., Mc Mahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S. and Boyd, M.R. (1990) New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. Journal of the National Cancer Institute, 82, 1107-1112.
http://dx.doi.org/10.1093/jnci/82.13.1107
[19]  Williams, W.B., Cuvelier, M.E., Berset, C. and Lebensm,W. (1995) Use of a Free Radical Method to Evaluate Antioxidant Activity. LWT-Food Science and Technology, 28, 25-30.
http://dx.doi.org/10.1016/S0023-6438(95)80008-5
[20]  Boger, D.L. and Nakahara, S. (1991) Diels-Alder Reactions of N-Sulfonyl-1-Aza-1,3-Butadienes: Development of a Synthetic approach to the Streptonigrone C Ring. Journal of Organic Chemistry, 56, 880-884.
http://dx.doi.org/10.1021/jo00002a077
[21]  Zhang, T.Y., Stout, J.R., Keay, J.G., Scriven, E.F.V., Toomey, J.E. and Goe, G.L. (1995) Regioselective Synthesis of 2-Chloro-3-Pyridinecarboxylates. Tetrahedron, 51, 13177-13184.
http://dx.doi.org/10.1016/0040-4020(95)00788-A
[22]  Ma, X. and Gang, D.R. (2004) The Lycopodium Alkaloids. Natural Product Reports, 21, 752-772.
http://dx.doi.org/10.1039/b409720n
[23]  George, R. and Thomas, H. (1934) The Synthesis of Pyridylpyrazoles. Journal of the Chemical Society (Resumed), 1739-1741.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133