Copyright (c) 2019 AJC
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Synthesis of Sulfonated Dihydrofuropyrazoles Derivatives as Antimicrobial Active Agents
Corresponding Author(s) : Venkata Swamy Tangeti
Asian Journal of Chemistry,
Vol. 31 No. 4 (2019): Vol 31 Issue 4
Abstract
A series of sulfonyl dihydrofuropyrazole derivatives was prepared from one pot multi component condensation of sulfonated β-keto ester, aromatic aldehyde, hydrazine, pyridinium ylide in presence of piperidine catalyst under ethanol solvent conditions and subsequent oxidation of SPh group with MCPBA. All the synthesized compounds were characterized by analytical and spectral techniques and screened in vitro for antimicrobial activity. The activity data revealed that most of the compounds exhibited good to significant activities. Compounds 6b, 6i, 6j, 6k, 6m, 6n exhibited good and broad spectrum activity towards all the tested bacterial strains.
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- D. Muñoz-Torrero, A.A. Mangoni, C. Guillou, S. Collina, J.J. Vanden Eynde, J. Rautio, G.M. Keseru, C. Hulme, K. Chibale, F.J. Luque, R. Karaman, M. Gütschow, H. Liu and R. Ragno, Molecules, 22, 743 (2017); https://doi.org/10.3390/molecules22050743.
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References
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E. Low, B. Kim, C. Francavilla, T.P. Shiau, E.D. Turtle, D.J.R. O’Mahony, N. Alvarez, A. Houchin, P. Xu, M. Zuck, C. Celeri, M.B. Anderson, R.R. Najafi and R.K. Jain, Bioorg. Med. Chem. Lett., 21, 3682 (2011); https://doi.org/10.1016/j.bmcl.2011.04.084.
V.S. Pilyugin, S.L. Kuznetsova, Y.E. Sapozhnikov, G.E. Chikisheva, G.V. Kiseleva, T.P. Vorob’eva, E.V. Klimakova, N.A. Sapozhnikova, R.D. Davletov and Z.B. Galeeva, Russ. J. Gen. Chem., 78, 446 (2008); https://doi.org/10.1134/S1070363208030195.
Y. Dixit, R. Dixit, N. Gautam and D.C. Gautam, E-J. Chem., 5(s1), 1063 (2008); https://doi.org/10.1155/2008/809419.
L.V. Kumar, P.J. Naik, M. Naveen, T. Chandrasekhar, A.B. Reddy and N. Penchalaiah, Indian J. Chem., 53B, 208 (2014).
A.B.V.K. Kumar, K.S.V.K. Rao, M.S. Chandra, M.C.S. Subha and Y.L. Choi, J. Korean Soc. Appl. Biol. Chem., 52, 34 (2009); https://doi.org/10.3839/jksabc.2009.006.
A. Wani and S. Mahajan, Am. J. Pharm. Tech. Res., 4, 1058 (2014).
B. Guruswamy, R.K. Arul, M.V.S.R.K. Chaitan and S.S.P.K. Darsi, Eur. J. Chem., 4, 329 (2013); https://doi.org/10.5155/eurjchem.4.4.329-335.792.
S. Barbuceanu, G.L. Almajan, I. Saramet, C. Draghici, R. Socoteanu and F. Barbuceanu, J. Serb. Chem. Soc., 74, 1041 (2009); https://doi.org/10.2298/JSC0910041B.
S. Soni, M. Seth and P. Sah, Res. J. Pharm. Biol. Chem. Sci., 3, 898 (2012).
K.V. Kudryavtsev, M.L. Bentley and D.G. McCafferty, Bioorg. Med. Chem., 17, 2886 (2009); https://doi.org/10.1016/j.bmc.2009.02.008.
H. Otten, J. Antimicrob. Chemother., 17, 689 (1986); https://doi.org/10.1093/jac/17.6.689.
G. Schernthaner, A. Grimaldi, U. Di Mario, J. Drzewoski, P. Kempler, M. Kvapil, A. Novials, R. Rottiers, G.E.H.M. Rutten and K.M. Shaw, Eur. J. Clin. Invest., 34, 535 (2004); https://doi.org/10.1111/j.1365-2362.2004.01381.x.
C. Reviriego, Drugs Future, 37, 247 (2012); https://doi.org/10.1358/dof.2012.037.04.1789350.
M.J. Yelland, C.J. Nikles, N. McNairn, C.B. Del Mar, P.J. Schluter and R.M. Brown, Rheumatology, 46, 135 (2007); https://doi.org/10.1093/rheumatology/kel195.
S.G. Kang and J.J. Kim, Ther. Adv. Urol., 5, 101 (2013); https://doi.org/10.1177/1756287212470019.
C.L. Lawrence, P. Proks, G.C. Rodrigo, P. Jones, Y. Hayabuchi, N.B. Standen and F.M. Ashcroft, Diabetologia, 44, 1019 (2001); https://doi.org/10.1007/s001250100595.
V.S. Tangeti, R. Varma K, G.V. Siva Prasad and K.V.V.V. Satyanarayana, Synth. Commun., 46, 613 (2016); https://doi.org/10.1080/00397911.2016.1159696.
S.V.H.S. Bhaskaruni, S.Maddila, K.K. Gangu and S.B. Jonnalagadda, Arab. J. Chem., (2017); https://doi.org/10.1016/j.arabjc.2017.09.016.
M.S. Singh and S. Chowdhury, RSC Adv., 2, 4547 (2012); https://doi.org/10.1039/C2RA01056A.
V.S. Tangeti, B.H. Reddy and P. Sombabu, Der Pharma Chemica, 9, 1 (2017).
M. Hossain and A.K. Nanda, Sci. J. Chem., 6, 83 (2018); https://doi.org/10.11648/j.sjc.20180605.12.
V.S. Tangeti, K.R. Babu, D. Vasundhara, K.V.V.V. Satyanarayana, H. Mylapalli and K.S.P. Kumar, Curr. Org. Synth., 15, 267 (2018); https://doi.org/10.2174/1570179414666171011161836.
V.S. Tangeti, K.R. Babu, G.V.S. Prasad and P. Venkata Rao, J. Indian Chem. Soc., 15, 823 (2018).
V.S. Tangeti, G.V. Siva Prasad, J. Panda, K.R. Varma and K.R. Varma, Synth. Commun., 46, 878 (2016); https://doi.org/10.1080/00397911.2016.1174781.
H. Prakash Rao, S. Rafi and K. Padmavathy, Lett. Org. Chem., 5, 527 (2008); https://doi.org/10.2174/157017808785982121.
H.S.P. Rao and N. Muthanna, Synlett, 27, 2014 (2016); https://doi.org/10.1055/s-0035-1561662.
S.M. Rajesh, S. Perumal, J.C. Menéndez, S. Pandian and R. Murugesan, Tetrahedron, 68, 5631 (2012); https://doi.org/10.1016/j.tet.2012.04.058.
J.G. Cappucino and N. Sherman, Cultivation of Microorganisms: Nutritional and Physical Requirements, and Enumeration of Microbial Population. In: Microbiology − A Laboratory Manual, Addison Wesley Longman Inc.: Harlow, edn 4, p. 263 (1999).