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Design, Microwave Assisted Synthesis and Characterization of Substituted 1,2,4-Oxadiazole Analogues as Promising Pharmacological Agents
Corresponding Author(s) : Katharigatta N. Venugopala
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
Microwave assisted synthesis of a series of 3,5-disubstituted-1,2,4-oxadiazole analogues (3a-j) has been achieved between 5-(chloromethyl)-3-substituted phenyl-1,2,4-oxadiazoles (2a-j) and substituted benzophenone in presence of potassium carbonate in acetone medium. The structural elucidation of the newly synthesized 1,2,4-oxadiazole analogues was established by means of FT-IR, NMR, LC-MS and elemental analysis.
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- L.A. Kayukova, K.D. Praliev, A.L. Akhelova, U.S. Kemel’bekov, G.M. Pichkhadze, G.S. Mukhamedzhanova, D.M. Kadyrova and S.R. Nasyrova, Pharm. Chem. J., 45, 468 (2011); https://doi.org/10.1007/s11094-011-0657-0.
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- F.A. Abulwerdi, M.D. Shortridge, J. Sztuba-Solinska, R. Wilson, S.F.J. Le Grice, G. Varani and J.S. Schneekloth Jr., J. Med. Chem., 59, 11148 (2016); https://doi.org/10.1021/acs.jmedchem.6b01450.
- D.R. Guda, S.-J. Park, M.-W. Lee, T.-J. Kim and M.E. Lee, Eur. J. Med. Chem., 62, 84 (2013); https://doi.org/10.1016/j.ejmech.2012.12.035.
- R. Hamdy, N.I. Ziedan, S. Ali, C. Bordoni, M. El-Sadek, E. Lashin, A. Brancale, A.T. Jones and A.D. Westwell, Bioorg. Med. Chem. Lett., 27, 1037 (2017); https://doi.org/10.1016/j.bmcl.2016.12.061.
- M. Mohammadi-Khanaposhtani, M. Shabani, M. Faizi, I. Aghaei, R. Jahani, Z. Sharafi, N. Shamsaei Zafarghandi, M. Mahdavi, T. Akbarzadeh, S. Emami, A. Shafiee and A. Foroumadi, Eur. J. Med. Chem., 112, 91 (2016); https://doi.org/10.1016/j.ejmech.2016.01.054.
- V.B. Iyer, B. Gurupadayya, V.S. Koganti, B. Inturi and R.S. Chandan, Med. Chem. Res., 26, 190 (2017); https://doi.org/10.1007/s00044-016-1740-6.
- N.P. Rai, V.K. Narayanaswamy, S. Shashikanth and P.N. Arunachalam, Eur. J. Med. Chem., 44, 4522 (2009); https://doi.org/10.1016/j.ejmech.2009.06.020.
- K. Bethge, H.H. Pertz and K. Rehse, Arch. Pharm., 338, 78 (2005); https://doi.org/10.1002/ardp.200400927.
- J. Suzuki, D. Okamura, T. Gushikawa, K. Hirai and T. Ando, J. Pestic. Sci., 36, 392 (2011); https://doi.org/10.1584/jpestics.G11-28.
- Y. Wang, C. Zhang, B. Zhu, Q. Li and H. Zhang, Patent No. CN104016939A (2014).
- T. M. Twose, M. L. Verdone, R. C. Copp and J. G. Farnham, Patent No. WO2012030314A1 (2012).
- J.W. Clitherow, P. Beswick, W.J. Irving, D.I.C. Scopes, J.C. Barnes, J. Clapham, J.D. Brown, D.J. Evans and A.G. Hayes, Bioorg. Med. Chem. Lett., 6, 833 (1996); https://doi.org/10.1016/0960-894X(96)00122-9.
- K.N. Venugopala, G.K. Rao, P.N.S. Pai and G.L. Ganesh, Orient. J. Chem., 23, 1093 (2007).
- A. Pathak, K.N. Venugopala, A. Joshi, G.K. Rao and K. Devi, Indian J. Heterocycl. Chem., 19, 273 (2010).
- K.N. Venugopala, D. Rao, S. Bhandary, M. Pillay, D. Chopra, B. Aldhubiab, M. Attimarad, O. Alwassil, S. Harsha and K. Mlisana, Drug Des. Devel. Ther., 10, 2681 (2016); https://doi.org/10.2147/DDDT.S109760.
- G.B. Dharma Rao, S. Bhandary, D. Chopra, K.N. Venugopala, R.M. Gleiser, K. Kasumbwe and B. Odhav, Chem. Biol. Drug Des., (2017); https://doi.org/10.1111/cbdd.12957.
- P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Crystallogr. B, 70, 681 (2014); https://doi.org/10.1107/S2052520614006209.
- P. Munshi, K.N. Venugopala, B.S. Jayashree and T.N. Guru Row, Cryst. Growth Des., 4, 1105 (2004); https://doi.org/10.1021/cg049948l.
- K.N. Venugopala, S.K. Nayak, R.M. Gleiser, M.E. Sanchez-Borzone, D.A. Garcia and B. Odhav, Chem. Biol. Drug Des., 88, 88 (2016); https://doi.org/10.1111/cbdd.12736.
References
L.A. Kayukova, K.D. Praliev, A.L. Akhelova, U.S. Kemel’bekov, G.M. Pichkhadze, G.S. Mukhamedzhanova, D.M. Kadyrova and S.R. Nasyrova, Pharm. Chem. J., 45, 468 (2011); https://doi.org/10.1007/s11094-011-0657-0.
A. Shaikh and J. Meshram, J. Heterocycl. Chem., 53, 1176 (2016); https://doi.org/10.1002/jhet.2377.
F.A. Abulwerdi, M.D. Shortridge, J. Sztuba-Solinska, R. Wilson, S.F.J. Le Grice, G. Varani and J.S. Schneekloth Jr., J. Med. Chem., 59, 11148 (2016); https://doi.org/10.1021/acs.jmedchem.6b01450.
D.R. Guda, S.-J. Park, M.-W. Lee, T.-J. Kim and M.E. Lee, Eur. J. Med. Chem., 62, 84 (2013); https://doi.org/10.1016/j.ejmech.2012.12.035.
R. Hamdy, N.I. Ziedan, S. Ali, C. Bordoni, M. El-Sadek, E. Lashin, A. Brancale, A.T. Jones and A.D. Westwell, Bioorg. Med. Chem. Lett., 27, 1037 (2017); https://doi.org/10.1016/j.bmcl.2016.12.061.
M. Mohammadi-Khanaposhtani, M. Shabani, M. Faizi, I. Aghaei, R. Jahani, Z. Sharafi, N. Shamsaei Zafarghandi, M. Mahdavi, T. Akbarzadeh, S. Emami, A. Shafiee and A. Foroumadi, Eur. J. Med. Chem., 112, 91 (2016); https://doi.org/10.1016/j.ejmech.2016.01.054.
V.B. Iyer, B. Gurupadayya, V.S. Koganti, B. Inturi and R.S. Chandan, Med. Chem. Res., 26, 190 (2017); https://doi.org/10.1007/s00044-016-1740-6.
N.P. Rai, V.K. Narayanaswamy, S. Shashikanth and P.N. Arunachalam, Eur. J. Med. Chem., 44, 4522 (2009); https://doi.org/10.1016/j.ejmech.2009.06.020.
K. Bethge, H.H. Pertz and K. Rehse, Arch. Pharm., 338, 78 (2005); https://doi.org/10.1002/ardp.200400927.
J. Suzuki, D. Okamura, T. Gushikawa, K. Hirai and T. Ando, J. Pestic. Sci., 36, 392 (2011); https://doi.org/10.1584/jpestics.G11-28.
Y. Wang, C. Zhang, B. Zhu, Q. Li and H. Zhang, Patent No. CN104016939A (2014).
T. M. Twose, M. L. Verdone, R. C. Copp and J. G. Farnham, Patent No. WO2012030314A1 (2012).
J.W. Clitherow, P. Beswick, W.J. Irving, D.I.C. Scopes, J.C. Barnes, J. Clapham, J.D. Brown, D.J. Evans and A.G. Hayes, Bioorg. Med. Chem. Lett., 6, 833 (1996); https://doi.org/10.1016/0960-894X(96)00122-9.
K.N. Venugopala, G.K. Rao, P.N.S. Pai and G.L. Ganesh, Orient. J. Chem., 23, 1093 (2007).
A. Pathak, K.N. Venugopala, A. Joshi, G.K. Rao and K. Devi, Indian J. Heterocycl. Chem., 19, 273 (2010).
K.N. Venugopala, D. Rao, S. Bhandary, M. Pillay, D. Chopra, B. Aldhubiab, M. Attimarad, O. Alwassil, S. Harsha and K. Mlisana, Drug Des. Devel. Ther., 10, 2681 (2016); https://doi.org/10.2147/DDDT.S109760.
G.B. Dharma Rao, S. Bhandary, D. Chopra, K.N. Venugopala, R.M. Gleiser, K. Kasumbwe and B. Odhav, Chem. Biol. Drug Des., (2017); https://doi.org/10.1111/cbdd.12957.
P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Crystallogr. B, 70, 681 (2014); https://doi.org/10.1107/S2052520614006209.
P. Munshi, K.N. Venugopala, B.S. Jayashree and T.N. Guru Row, Cryst. Growth Des., 4, 1105 (2004); https://doi.org/10.1021/cg049948l.
K.N. Venugopala, S.K. Nayak, R.M. Gleiser, M.E. Sanchez-Borzone, D.A. Garcia and B. Odhav, Chem. Biol. Drug Des., 88, 88 (2016); https://doi.org/10.1111/cbdd.12736.