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This work is licensed under a Creative Commons Attribution 4.0 International License.
Green Synthesis, Characterization and Antidiabetic Activity of 2-Substituted Aryl/Alkyl-N-Aryl/Alkyl Imidazo[1,2-a]pyridin-3-amine Derivatives
Corresponding Author(s) : Tata Veereswara Rao Kota
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
Imidazo[1,2-a]pyridines containing ring junction have shown broad therapeutic properties in the drug discovery sector, such as the treatment of heart disease, migraines, digestive disease and viral disease. Imidazo[1,2-a]pyridine structure is very much prevalent in several marketed drugs viz., olprinone, zolpidem, levamisole, alpidem, zolimidine etc. The present paper describes the green synthesis of some novel imidazo[1,2-a]pyridine derivatives (6a-f/7a-f), a straight forward, isocyanide based Groebke-Blackburn-Bienayme, three component reactions in which aldehyde, 2-aminopyridine and isocyanide are condensed in presence of green parameters such as (i) ZnO nanoparticles/ZnFe2O4 nanoparticles (reusable heterogeneous catalysts), (ii) 2-methyl-tetrahydrofuran (green solvent) and (iii) microwave irradiation (energy efficiency reducing time period of the reaction). These derivatives were evaluated for antidiabetic experiments and the results revealed that most of the compounds were active towards antidiabetic property.
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References
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K.C. Rupert, J.R. Henry, J.H. Dodd, S.A. Wadsworth, D.E. Cavender, G.C. Olini, B. Fahmy and J. Siekierka, Bioorg. Med. Chem. Lett., 13, 347 (2003); https://doi.org/10.1016/S0960-894X(02)01020-X.
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T. Swainston Harrison and G.M. Keating, CNS Drugs, 19, 65 (2005); https://doi.org/10.2165/00023210-200519010-00008.
R.F. Holcombe, C.E. McLaren and T. Milovanovic, Cancer Detect. Prev., 30, 94 (2006); https://doi.org/10.1016/j.cdp.2005.08.002.
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J.J. Kaminski, B. Wallmark, C. Briving and B.M. Andersson, J. Med. Chem., 34, 533 (1991); https://doi.org/10.1021/jm00106a008.
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C. Blackburn, B. Guan, P. Fleming, K. Shiosaki and S. Tsai, Tetrahedron Lett., 39, 3635 (1998); https://doi.org/10.1016/S0040-4039(98)00653-4.
H. Xu, C. Ma, Z. Wu and G. Haung, Synthesis, 48, 351 (2016); https://doi.org/10.1055/s-0035-1560375.
R.B. Lacerda, C.K. de Lima, L.L. da Silva, N.C. Romeiro, A.L. Miranda, E.J. Barreiro and C.A. Fraga, Bioorg. Med. Chem., 17, 74 (2009); https://doi.org/10.1016/j.bmc.2008.11.018.
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H.A. Shinde, M. Srilaxmi, B. Satpathi and D.S. Sharada, Tetrahedron Lett., 55, 5915 (2014); https://doi.org/10.1016/j.tetlet.2014.08.126.
A.S. Kiselyov, Tetrahedron Lett., 46, 4487 (2005); https://doi.org/10.1016/j.tetlet.2005.04.124.
J. Dam, Z. Ismail, T. Kurebwa, N. Gangat, L. Harmse, H.M. Marques, A. Lemmerer, M.L. Bode and C.B. de Koning, Eur. J. Med. Chem., 126, 353 (2017); https://doi.org/10.1016/j.ejmech.2016.10.041.
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P.V. Raghavan, Expert Consultant, CPCSEA, OECD, Guideline No. 420 (2000).
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A.L. Rousseau, P. Matlaba and C.J. Parkinson, Tetrahedron Lett., 48, 4079 (2007); https://doi.org/10.1016/j.tetlet.2007.04.008.
L.R. Odell, M. Nilsson, J. Gising, O. Lagerlund, D. Muthas, A. Nordqvist, A. Karlen and M. Larhed, Bioorg. Med. Chem. Lett., 19, 4790 (2009); https://doi.org/10.1016/j.bmcl.2009.06.045.
S. Guchhait and C. Madaan, Synlett, 628 (2009); https://doi.org/10.1055/s-0028-1087915.
A. Shaabani, E. Soleimani, A. Sarvary, H. Rezayan and A. Maleki, Chin. J. Chem., 27, 369 (2009); https://doi.org/10.1002/cjoc.200990060.
A. Shaabani, E. Soleimani, A. Maleki and J. Moghimi-Rad, Synth. Commun., 38, 1090 (2008); https://doi.org/10.1080/00397910701862931.
R.S. Varma and D. Kumar, Tetrahedron Lett., 40, 7665 (1999); https://doi.org/10.1016/S0040-4039(99)01585-3.
M. Adib, M. Mahdavi, M.A. Noghani and P. Mirzaei, Tetrahedron Lett., 48, 7263 (2007); https://doi.org/10.1016/j.tetlet.2007.08.049.
S. Vidyacharan, A.H. Shinde, B. Satpathi and D.S. Sharada, Green Chem., 16, 1168 (2014); https://doi.org/10.1039/c3gc42130a.