This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Biological Evaluation of 1,3,4-Oxadiazole Fused Resveratrol Derivatives as Anticancer Agents
Corresponding Author(s) : Vema Venkata Naresh
Asian Journal of Chemistry,
Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020
Abstract
A novel target compounds (9a-j) were design and synthesized and characterized by 1H & 13C NMR, ESI-MS spectral analysis. Further, these were tested for their anticancer activity against three human cancer cell lines such as MCF-7, MDA MB-231 (breast), A549 (Lung) and adriamycin was used as positive control. Among ten compounds, two compounds like 9b and 9j were showed a significant anticancer activity compared to control drug.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- J.A. Baur and D.A. Sinclair, Nat. Rev. Drug Discov., 5, 493 (2006); https://doi.org/10.1038/nrd2060
- B.B. Aggarwall and S. Shishodia, Resveratrol in Health and Disease; Taylor & Francis: Boca Raton, FL, USA (2006).
- Y. Schneider, F. Vincent, B. Duranton, L. Badolo, F. Gosse, C. Bergmann, N. Seiler and F. Raul, Cancer Lett., 158, 85 (2000); https://doi.org/10.1016/S0304-3835(00)00511-5
- F. Uenobe, S. Nakamura and M. Miyazawa, Mutat. Res., 373, 197 (1997); https://doi.org/10.1016/S0027-5107(96)00191-1
- G.B. Mahady, Oxidat. Stress Dis., 20, 465 (2006).
- L.L. Creasy and M.J. Coffee, J. Am. Soc. Hortic. Sci., 113, 230 (1988).
- N. Kawada, S. Seki, M. Inoue and T. Kuroki, Hepatology, 27, 1265 (1998); https://doi.org/10.1002/hep.510270512
- J.J. Docherty, M.M.H. Fu, B.S. Stiffler, R.J. Limperos, C.M. Pokabla and A.L. DeLucia, Antiviral Res., 43, 145 (1999); https://doi.org/10.1016/S0166-3542(99)00042-X
- B.D. Gehm, J.M. McAndrews, P.Y. Chien and J.L. Jameson, Proc. Natl. Acad. Sci. USA, 94, 14138 (1997); https://doi.org/10.1073/pnas.94.25.14138
- M. Virgili and A. Contestabile, Neurosci. Lett., 281, 123 (2000); https://doi.org/10.1016/S0304-3940(00)00820-X
- Z.R. Wang, Y.Z. Huang, J.G. Zou, K.J. Cao, Y.N. Xu and J.M. Wu, Int. J. Mol. Med., 9, 77 (2002);https://doi.org/10.3892/ijmm.9.1.77
- P. Kopp, Eur. J. Endocrinol., 138, 619 (1998); https://doi.org/10.1530/eje.0.1380619
- X.P. Lei, B. Liu and N. Zhu, Zhongguo Xin Yao Zazhi, 9, 540 (2000).
- G.R. Pettit, S.B. Singh, M.L. Niven, E. Hamel and J.M. Schmidt, J. Nat. Prod., 50, 119 (1987); https://doi.org/10.1021/np50049a016
- G.R. Pettit, G.M. Cragg and S.B. Singh, J. Nat. Prod., 50, 386 (1987); https://doi.org/10.1021/np50051a008
- G.M. Tozer, C. Kanthou, C.S. Parkins and S.A. Hill, Int. J. Exp. Pathol., 83, 21 (2002); https://doi.org/10.1046/j.1365-2613.2002.00211.x
- S. Bondock, S. Adel, H.A. Etman and F.A. Badria, Eur. J. Med. Chem., 48, 192 (2012); https://doi.org/10.1016/j.ejmech.2011.12.013
- N.N. Farshori, M.R. Banday, A. Ahmad, A.U. Khan and A. Rauf, Bioorg. Med. Chem. Lett., 20, 1933 (2010); https://doi.org/10.1016/j.bmcl.2010.01.126
- A.A. El-Emam, O.A. Al-Deeb, M. Al-Omar and J. Lehmann, Bioorg. Med. Chem., 12, 5107 (2004); https://doi.org/10.1016/j.bmc.2004.07.033
- S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); https://doi.org/10.1016/S0223-5234(01)01326-5
- Y.H. Li, H.J. Zhu, K. Chen, R. Liu, A. Khallaf, X.N. Zhang and J.P. Ni, Org. Biomol. Chem., 11, 3979 (2013); https://doi.org/10.1039/c3ob40345a
- Z.N. Cui, Y.X. Shi, L. Zhang, Y. Ling, B.J. Li, Y. Nishida and X.L. Yang, J. Agric. Food Chem., 60, 11649 (2012); https://doi.org/10.1021/jf303807a
- M.Y. Wani, A. Ahmad, R.A. Shiekh, K.J. Al-Ghamdi and A.J.F.N. Sobral, Bioorg. Med. Chem., 23, 4172 (2015); https://doi.org/10.1016/j.bmc.2015.06.053
- B. Jayashankar, K.M. Lokanathrai, N. Baskaran and H.S. Sathish, Eur. J. Med. Chem., 44, 3898 (2009); https://doi.org/10.1016/j.ejmech.2009.04.006
- N. Ingale, V. Maddi, M. Palkar, P. Ronad, A.H.M. Vishwanathswamy, S. Mamledesai and D. Satyanarayana, Med. Chem. Res., 21, 16 (2012); https://doi.org/10.1007/s00044-010-9494-z
- D. Sriram, D. Banerjee and P. Yogeeswari, J. Enzyme Inhib. Med. Chem., 24, 1 (2009); https://doi.org/10.1080/14756360701404159
- M.T.H. Khan, M.I. Choudhary, K.M. Khan, M. Rani and Atta-ur-Rahman, Bioorg. Med. Chem., 13, 3385 (2005); https://doi.org/10.1016/j.bmc.2005.03.012
- A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); https://doi.org/10.1016/j.bmcl.2004.09.072
- Y. Li, Y. Luo, Y. Hu, D.-D. Zhu, S. Zhang, Z.-J. Liu, H.-B. Gong and H.-L. Zhu, Bioorg. Med. Chem., 20, 4316 (2012); https://doi.org/10.1016/j.bmc.2012.05.050
- K. Laskar, P. Alam, R.H. Khan and A. Rauf, Eur. J. Med. Chem., 122, 72 (2016);https://doi.org/10.1016/j.ejmech.2016.06.012
- A. Vaidya, S. Jain, P. Jain, P. Jain, N. Tiwari, R. Jain, R. Jain, A.K. Jain and R.K. Agrawal, Mini Rev. Med. Chem., 16, 825 (2016); https://doi.org/10.2174/1389557516666160211120835
- N.D. James and J.W. Growcott, Drugs Future, 34, 624 (2009);https://doi.org/10.1358/dof.2009.34.8.1400202
- M. Roberti, D. Pizzirani, D. Simoni, R. Rondanin, R. Baruchello, C. Bonora, F. Buscemi, S. Grimaudo and M. Tolomeo, J. Med. Chem., 46, 3546 (2003); https://doi.org/10.1021/jm030785u
- N.U.A. Mohsin and M. Irfan, J. Chil. Chem. Soc., 63, 4135 (2018); https://doi.org/10.4067/s0717-97072018000304135
- P.N. Reddy, P. Padmaja, B.R. Reddy, G. Rambabu and M.P. Kumar, Med. Chem. Res., 25, 2093 (2016); https://doi.org/10.1007/s00044-016-1676-x
- L. Li, S. Jiang, X. Li, Y. Liu, J. Su and J. Chen, Eur. J. Med. Chem., 151, 482 (2018);https://doi.org/10.1016/j.ejmech.2018.04.011
References
J.A. Baur and D.A. Sinclair, Nat. Rev. Drug Discov., 5, 493 (2006); https://doi.org/10.1038/nrd2060
B.B. Aggarwall and S. Shishodia, Resveratrol in Health and Disease; Taylor & Francis: Boca Raton, FL, USA (2006).
Y. Schneider, F. Vincent, B. Duranton, L. Badolo, F. Gosse, C. Bergmann, N. Seiler and F. Raul, Cancer Lett., 158, 85 (2000); https://doi.org/10.1016/S0304-3835(00)00511-5
F. Uenobe, S. Nakamura and M. Miyazawa, Mutat. Res., 373, 197 (1997); https://doi.org/10.1016/S0027-5107(96)00191-1
G.B. Mahady, Oxidat. Stress Dis., 20, 465 (2006).
L.L. Creasy and M.J. Coffee, J. Am. Soc. Hortic. Sci., 113, 230 (1988).
N. Kawada, S. Seki, M. Inoue and T. Kuroki, Hepatology, 27, 1265 (1998); https://doi.org/10.1002/hep.510270512
J.J. Docherty, M.M.H. Fu, B.S. Stiffler, R.J. Limperos, C.M. Pokabla and A.L. DeLucia, Antiviral Res., 43, 145 (1999); https://doi.org/10.1016/S0166-3542(99)00042-X
B.D. Gehm, J.M. McAndrews, P.Y. Chien and J.L. Jameson, Proc. Natl. Acad. Sci. USA, 94, 14138 (1997); https://doi.org/10.1073/pnas.94.25.14138
M. Virgili and A. Contestabile, Neurosci. Lett., 281, 123 (2000); https://doi.org/10.1016/S0304-3940(00)00820-X
Z.R. Wang, Y.Z. Huang, J.G. Zou, K.J. Cao, Y.N. Xu and J.M. Wu, Int. J. Mol. Med., 9, 77 (2002);https://doi.org/10.3892/ijmm.9.1.77
P. Kopp, Eur. J. Endocrinol., 138, 619 (1998); https://doi.org/10.1530/eje.0.1380619
X.P. Lei, B. Liu and N. Zhu, Zhongguo Xin Yao Zazhi, 9, 540 (2000).
G.R. Pettit, S.B. Singh, M.L. Niven, E. Hamel and J.M. Schmidt, J. Nat. Prod., 50, 119 (1987); https://doi.org/10.1021/np50049a016
G.R. Pettit, G.M. Cragg and S.B. Singh, J. Nat. Prod., 50, 386 (1987); https://doi.org/10.1021/np50051a008
G.M. Tozer, C. Kanthou, C.S. Parkins and S.A. Hill, Int. J. Exp. Pathol., 83, 21 (2002); https://doi.org/10.1046/j.1365-2613.2002.00211.x
S. Bondock, S. Adel, H.A. Etman and F.A. Badria, Eur. J. Med. Chem., 48, 192 (2012); https://doi.org/10.1016/j.ejmech.2011.12.013
N.N. Farshori, M.R. Banday, A. Ahmad, A.U. Khan and A. Rauf, Bioorg. Med. Chem. Lett., 20, 1933 (2010); https://doi.org/10.1016/j.bmcl.2010.01.126
A.A. El-Emam, O.A. Al-Deeb, M. Al-Omar and J. Lehmann, Bioorg. Med. Chem., 12, 5107 (2004); https://doi.org/10.1016/j.bmc.2004.07.033
S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); https://doi.org/10.1016/S0223-5234(01)01326-5
Y.H. Li, H.J. Zhu, K. Chen, R. Liu, A. Khallaf, X.N. Zhang and J.P. Ni, Org. Biomol. Chem., 11, 3979 (2013); https://doi.org/10.1039/c3ob40345a
Z.N. Cui, Y.X. Shi, L. Zhang, Y. Ling, B.J. Li, Y. Nishida and X.L. Yang, J. Agric. Food Chem., 60, 11649 (2012); https://doi.org/10.1021/jf303807a
M.Y. Wani, A. Ahmad, R.A. Shiekh, K.J. Al-Ghamdi and A.J.F.N. Sobral, Bioorg. Med. Chem., 23, 4172 (2015); https://doi.org/10.1016/j.bmc.2015.06.053
B. Jayashankar, K.M. Lokanathrai, N. Baskaran and H.S. Sathish, Eur. J. Med. Chem., 44, 3898 (2009); https://doi.org/10.1016/j.ejmech.2009.04.006
N. Ingale, V. Maddi, M. Palkar, P. Ronad, A.H.M. Vishwanathswamy, S. Mamledesai and D. Satyanarayana, Med. Chem. Res., 21, 16 (2012); https://doi.org/10.1007/s00044-010-9494-z
D. Sriram, D. Banerjee and P. Yogeeswari, J. Enzyme Inhib. Med. Chem., 24, 1 (2009); https://doi.org/10.1080/14756360701404159
M.T.H. Khan, M.I. Choudhary, K.M. Khan, M. Rani and Atta-ur-Rahman, Bioorg. Med. Chem., 13, 3385 (2005); https://doi.org/10.1016/j.bmc.2005.03.012
A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); https://doi.org/10.1016/j.bmcl.2004.09.072
Y. Li, Y. Luo, Y. Hu, D.-D. Zhu, S. Zhang, Z.-J. Liu, H.-B. Gong and H.-L. Zhu, Bioorg. Med. Chem., 20, 4316 (2012); https://doi.org/10.1016/j.bmc.2012.05.050
K. Laskar, P. Alam, R.H. Khan and A. Rauf, Eur. J. Med. Chem., 122, 72 (2016);https://doi.org/10.1016/j.ejmech.2016.06.012
A. Vaidya, S. Jain, P. Jain, P. Jain, N. Tiwari, R. Jain, R. Jain, A.K. Jain and R.K. Agrawal, Mini Rev. Med. Chem., 16, 825 (2016); https://doi.org/10.2174/1389557516666160211120835
N.D. James and J.W. Growcott, Drugs Future, 34, 624 (2009);https://doi.org/10.1358/dof.2009.34.8.1400202
M. Roberti, D. Pizzirani, D. Simoni, R. Rondanin, R. Baruchello, C. Bonora, F. Buscemi, S. Grimaudo and M. Tolomeo, J. Med. Chem., 46, 3546 (2003); https://doi.org/10.1021/jm030785u
N.U.A. Mohsin and M. Irfan, J. Chil. Chem. Soc., 63, 4135 (2018); https://doi.org/10.4067/s0717-97072018000304135
P.N. Reddy, P. Padmaja, B.R. Reddy, G. Rambabu and M.P. Kumar, Med. Chem. Res., 25, 2093 (2016); https://doi.org/10.1007/s00044-016-1676-x
L. Li, S. Jiang, X. Li, Y. Liu, J. Su and J. Chen, Eur. J. Med. Chem., 151, 482 (2018);https://doi.org/10.1016/j.ejmech.2018.04.011