Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Structural Elucidation of Novel 2,4-Disubstituted 1,3-Oxazole Analogues for Pharmacological Properties
Corresponding Author(s) : Katharigatta N. Venugopala
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
A series of novel 2,4-disubstituted 1,3-oxazole analogues (3a-i) has been designed and synthesized between 1-[3,5-bis(trifluoromethyl)-phenyl]-2-bromoethan-1-one and substituted amides by microwave assisted method. 2,4-Disubstituted 1,3-oxazole analogues obtained were at excellent yields and purity of the compound was ascertained by HPLC. The chemical structure of these compounds was elucidated by spectrometric (FT-IR, NMR and LCMS) and elemental analysis. It was observed that, microwave method influenced the better yield and reduction in reaction time when compared to conventional reflux method.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- A.C. Giddens, H.I.M. Boshoff, S.G. Franzblau, C.E. Barry III and B.R. Copp, Tetrahedron Lett., 46, 7355 (2005); https://doi.org/10.1016/j.tetlet.2005.08.119.
- R. Jansen, B. Kunze, H. Reichenbach and G. Höfle, Eur. J. Org. Chem., 917 (2002); https://doi.org/10.1002/1099-0690(200203)2002:5<917::AIDEJOC917>3.0.CO;2-Z.
- P. Wipf and S. Lim, J. Am. Chem. Soc., 117, 558 (1995); https://doi.org/10.1021/ja00106a075.
- D. Janssen, D. Albert, R. Jansen, R. Müller and M. Kalesse, Angew. Chem. Int. Ed., 46, 4898 (2007); https://doi.org/10.1002/anie.200605198.
- R.J. Mulder, C.M. Shafer and T.F. Molinski, J. Org. Chem., 64, 4995 (1999); https://doi.org/10.1021/jo9906328.
- J.D. White, P.R. Blakemore, N.J. Green, E.B. Hauser, M.A. Holoboski, L.E. Keown, C.S. Nylund Kolz and B.W. Phillips, J. Org. Chem., 67, 7750 (2002); https://doi.org/10.1021/jo020537q.
- B.S. Joshi, W.I. Taylor, D.S. Bhate and S.S. Karmarkar, Tetrahedron, 19, 1437 (1963); https://doi.org/10.1016/S0040-4020(01)98569-2.
- I.J. Turchi, Ind. Eng. Chem. Prod. Res. Dev., 20, 32 (1981); https://doi.org/10.1021/i300001a005.
- N.S. Kuppuswamy, R.K. Sundarraja, K. Shridhara, S.P. Nayak, S.P. Thomas, T.N. Guru Row, K. Pari and S. Jithendranath, Indian J. Chem., 56B, 145 (2017).
- Y.K. Abhale, A.V. Sasane, A.P. Chavan, S.H. Shekh, K.K. Deshmukh, S. Bhansali, L. Nawale, D. Sarkar and P.C. Mhaske, Eur. J. Med. Chem., 132, 333 (2017); https://doi.org/10.1016/j.ejmech.2017.03.065.
- A.M. Thompson, P.D. O’Connor, A. Blaser, V. Yardley, L. Maes, S. Gupta, D. Launay, D. Martin, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma and W.A. Denny, J. Med. Chem., 59, 2530 (2016); https://doi.org/10.1021/acs.jmedchem.5b01699.
- H.A. Blair and L.J. Scott, Drugs, 75, 91 (2015); https://doi.org/10.1007/s40265-014-0331-4.
- A.J. Robles, S. McCowen, S. Cai, M. Glassman, F. Ruiz II, R.H. Cichewicz, S.F. McHardy and S.L. Mooberry, J. Med. Chem., 60, 9275 (2017); https://doi.org/10.1021/acs.jmedchem.7b01228.
- T. Guo, Tetrahedron Lett., 57, 5837 (2016); https://doi.org/10.1016/j.tetlet.2016.11.056.
- M.-X. Song, B.-Q. Rao, B.-B. Cheng, B.S.P. Yi, B.S.P. Wu, H. Zeng, Y. Luo and X.-Q. Deng, CNS Neurol. Disord. Drug Targets, 16, 187 (2017); https://doi.org/10.2174/1871527315666160822112501.
- U.H. Lindberg, Acta Pharm. Suec., 8, 647 (1971).
- A.S.A. Youssef, K.A. Kandeel, W.S.I. Abou-Elmagd and D.S.A. Haneen, J. Heterocycl. Chem., 53, 809 (2016); https://doi.org/10.1002/jhet.2329.
- W. Li, S. Li, L. Mao, Y. Jiang, G. Xu, W. Dong, J. Shen and T. Jiang, Chinese Patent CN104817549A (2015).
- S.M. Sondhi, R.P. Verma, N. Singhal, V.K. Sharma, C. Husiu, L. Vargiu, S. Longu and P. La Colla, Indian J. Pharm. Sci., 62, 71 (2000).
- N.R. Stokes, N. Baker, J.M. Bennett, P.K. Chauhan, I. Collins, D.T. Davies, M. Gavade, D. Kumar, P. Lancett, R. Macdonald, L. Macleod, A. Mahajan, J.P. Mitchell, N. Nayal, Y.N. Nayal, G.R. Pitt, M. Singh, A. Yadav, A. Srivastava, L.G. Czaplewski and D.J. Haydon, Bioorg. Med. Chem. Lett., 24, 353 (2014); https://doi.org/10.1016/j.bmcl.2013.11.002.
- M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); https://doi.org/10.2174/157018009787158481.
- M.C. Walker and M.C.Y. Chang, Chem. Soc. Rev., 43, 6527 (2014); https://doi.org/10.1039/C4CS00027G.
- J.R. Woods, H. Mo, A.A. Bieberich, T. Alavanja and D.A. Colby, J. Med. Chem., 54, 7934 (2011); https://doi.org/10.1021/jm201114t.
- P. Zhou, J. Zou, F. Tian and Z. Shang, J. Chem. Inf. Model., 49, 2344 (2009); https://doi.org/10.1021/ci9002393.
- X. Huang, J. Ding, H. Wu, X. Tian and M. Liu, Zhongguo Yaowu Huaxue Zazhi, 17, 111 (2007).
- C. Botteghi, G.D. Ponte, M. Marchetti and S. Paganelli, J. Mol. Catal., 93, 1 (1994); https://doi.org/10.1016/0304-5102(94)00077-8.
- K.N. Venugopala and B.S. Jayashree, Indian J. Pharm. Sci., 70, 88 (2008); https://doi.org/10.4103/0250-474X.40338.
- K. Kasumbwe, K. N. Venugopala, V. Mohanlall and B. Odhav, Anticancer. Agents Med. Chem., 17, 276 (2017); https://doi.org/10.2174/1871520616666160926112508.
- K. 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.
- C. Sandeep, B. Padmashali, K.N. Venugopala, R.S. Kulkarni, R. Venugopala and B. Odhav, Asian J. Chem., 28, 1043 (2016); https://doi.org/10.14233/ajchem.2016.19582.
- 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.
- P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Cryst. Sect. B Str. Sci., 70, 681 (2014); https://doi.org/10.1107/S2052520614006209.
- R.M. Cowper and L.H. Davidson, Organic Syntheses, John Wiley & Sons, Inc. (2003).
- K.N. Venugopala and B.S. Jayashree, Indian J. Pharm. Sci., 70, 88 (2008); https://doi.org/10.4103/0250-474X.40338.
References
A.C. Giddens, H.I.M. Boshoff, S.G. Franzblau, C.E. Barry III and B.R. Copp, Tetrahedron Lett., 46, 7355 (2005); https://doi.org/10.1016/j.tetlet.2005.08.119.
R. Jansen, B. Kunze, H. Reichenbach and G. Höfle, Eur. J. Org. Chem., 917 (2002); https://doi.org/10.1002/1099-0690(200203)2002:5<917::AIDEJOC917>3.0.CO;2-Z.
P. Wipf and S. Lim, J. Am. Chem. Soc., 117, 558 (1995); https://doi.org/10.1021/ja00106a075.
D. Janssen, D. Albert, R. Jansen, R. Müller and M. Kalesse, Angew. Chem. Int. Ed., 46, 4898 (2007); https://doi.org/10.1002/anie.200605198.
R.J. Mulder, C.M. Shafer and T.F. Molinski, J. Org. Chem., 64, 4995 (1999); https://doi.org/10.1021/jo9906328.
J.D. White, P.R. Blakemore, N.J. Green, E.B. Hauser, M.A. Holoboski, L.E. Keown, C.S. Nylund Kolz and B.W. Phillips, J. Org. Chem., 67, 7750 (2002); https://doi.org/10.1021/jo020537q.
B.S. Joshi, W.I. Taylor, D.S. Bhate and S.S. Karmarkar, Tetrahedron, 19, 1437 (1963); https://doi.org/10.1016/S0040-4020(01)98569-2.
I.J. Turchi, Ind. Eng. Chem. Prod. Res. Dev., 20, 32 (1981); https://doi.org/10.1021/i300001a005.
N.S. Kuppuswamy, R.K. Sundarraja, K. Shridhara, S.P. Nayak, S.P. Thomas, T.N. Guru Row, K. Pari and S. Jithendranath, Indian J. Chem., 56B, 145 (2017).
Y.K. Abhale, A.V. Sasane, A.P. Chavan, S.H. Shekh, K.K. Deshmukh, S. Bhansali, L. Nawale, D. Sarkar and P.C. Mhaske, Eur. J. Med. Chem., 132, 333 (2017); https://doi.org/10.1016/j.ejmech.2017.03.065.
A.M. Thompson, P.D. O’Connor, A. Blaser, V. Yardley, L. Maes, S. Gupta, D. Launay, D. Martin, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma and W.A. Denny, J. Med. Chem., 59, 2530 (2016); https://doi.org/10.1021/acs.jmedchem.5b01699.
H.A. Blair and L.J. Scott, Drugs, 75, 91 (2015); https://doi.org/10.1007/s40265-014-0331-4.
A.J. Robles, S. McCowen, S. Cai, M. Glassman, F. Ruiz II, R.H. Cichewicz, S.F. McHardy and S.L. Mooberry, J. Med. Chem., 60, 9275 (2017); https://doi.org/10.1021/acs.jmedchem.7b01228.
T. Guo, Tetrahedron Lett., 57, 5837 (2016); https://doi.org/10.1016/j.tetlet.2016.11.056.
M.-X. Song, B.-Q. Rao, B.-B. Cheng, B.S.P. Yi, B.S.P. Wu, H. Zeng, Y. Luo and X.-Q. Deng, CNS Neurol. Disord. Drug Targets, 16, 187 (2017); https://doi.org/10.2174/1871527315666160822112501.
U.H. Lindberg, Acta Pharm. Suec., 8, 647 (1971).
A.S.A. Youssef, K.A. Kandeel, W.S.I. Abou-Elmagd and D.S.A. Haneen, J. Heterocycl. Chem., 53, 809 (2016); https://doi.org/10.1002/jhet.2329.
W. Li, S. Li, L. Mao, Y. Jiang, G. Xu, W. Dong, J. Shen and T. Jiang, Chinese Patent CN104817549A (2015).
S.M. Sondhi, R.P. Verma, N. Singhal, V.K. Sharma, C. Husiu, L. Vargiu, S. Longu and P. La Colla, Indian J. Pharm. Sci., 62, 71 (2000).
N.R. Stokes, N. Baker, J.M. Bennett, P.K. Chauhan, I. Collins, D.T. Davies, M. Gavade, D. Kumar, P. Lancett, R. Macdonald, L. Macleod, A. Mahajan, J.P. Mitchell, N. Nayal, Y.N. Nayal, G.R. Pitt, M. Singh, A. Yadav, A. Srivastava, L.G. Czaplewski and D.J. Haydon, Bioorg. Med. Chem. Lett., 24, 353 (2014); https://doi.org/10.1016/j.bmcl.2013.11.002.
M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); https://doi.org/10.2174/157018009787158481.
M.C. Walker and M.C.Y. Chang, Chem. Soc. Rev., 43, 6527 (2014); https://doi.org/10.1039/C4CS00027G.
J.R. Woods, H. Mo, A.A. Bieberich, T. Alavanja and D.A. Colby, J. Med. Chem., 54, 7934 (2011); https://doi.org/10.1021/jm201114t.
P. Zhou, J. Zou, F. Tian and Z. Shang, J. Chem. Inf. Model., 49, 2344 (2009); https://doi.org/10.1021/ci9002393.
X. Huang, J. Ding, H. Wu, X. Tian and M. Liu, Zhongguo Yaowu Huaxue Zazhi, 17, 111 (2007).
C. Botteghi, G.D. Ponte, M. Marchetti and S. Paganelli, J. Mol. Catal., 93, 1 (1994); https://doi.org/10.1016/0304-5102(94)00077-8.
K.N. Venugopala and B.S. Jayashree, Indian J. Pharm. Sci., 70, 88 (2008); https://doi.org/10.4103/0250-474X.40338.
K. Kasumbwe, K. N. Venugopala, V. Mohanlall and B. Odhav, Anticancer. Agents Med. Chem., 17, 276 (2017); https://doi.org/10.2174/1871520616666160926112508.
K. 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.
C. Sandeep, B. Padmashali, K.N. Venugopala, R.S. Kulkarni, R. Venugopala and B. Odhav, Asian J. Chem., 28, 1043 (2016); https://doi.org/10.14233/ajchem.2016.19582.
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.
P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Cryst. Sect. B Str. Sci., 70, 681 (2014); https://doi.org/10.1107/S2052520614006209.
R.M. Cowper and L.H. Davidson, Organic Syntheses, John Wiley & Sons, Inc. (2003).
K.N. Venugopala and B.S. Jayashree, Indian J. Pharm. Sci., 70, 88 (2008); https://doi.org/10.4103/0250-474X.40338.