Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Green Synthesis, Molecular Docking and Cytotoxicity of (E)-1-(4-(Difluoromethoxy)-2-Hydroxybenzylidene) Semicarbazide
Corresponding Author(s) : Chinnadurai Anbuselvan
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
A green, one-pot three-components reaction of (E)-1-(4-(difluoromethoxy)-2-hydroxybenzylidene) semicarbazide has been designed, synthesized and characterized by elemental, FT-IR, 1H and 13C NMR spectral data. The cytotoxic activities of the synthesized compound were evaluated by MTT assay in human cancer cell lines. Docking studies of 3-substituted indolin-2-one scaffolds on vascular endothelial growth factor receptor 2 (VEGFR-2) involved in cell proliferation and angiogenesis was performed. Based on the ligand efficiency indices, Schiff bases may be regarded as efficient candidates for further molecular developments of anticancer agents. The molecule is useful in sensing and drug-carrying applications.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- W. Al Zoubi, Int. J. Org. Chem., 3, Article ID: 40184 (2013); https://doi.org/10.4236/ijoc.2013.33A008.
- G. Bringmann, M. Dreyer, J.H. Faber, P.W. Dalsgaard, J.W. Jaroszewski, H. Ndangalasi, F. Mbago, R. Brun and S.B. Christensen, J. Nat. Prod., 67, 743 (2004); https://doi.org/10.1021/np0340549.
- E. Horak, P. Kassal, M. Hranjec and I.M. Steinberg, Sens. Actuators B Chem., 258, 415 (2018); https://doi.org/10.1016/j.snb.2017.11.121.
- P. Rathelot, P. Vanelle, M. Gasquet, F. Delmas, M.P. Crozet, P. TimonDavid and J. Maldonado, Eur. J. Med. Chem., 30, 503 (1995); https://doi.org/10.1016/0223-5234(96)88261-4.
- A.A. Shanty, J.E. Philip, E.J. Sneha, M.R.P. Kurup, S. Balachandran and P.V. Mohanan, Bioorg. Chem., 70, 67 (2017). https://doi.org/10.1016/j.bioorg.2016.11.009.
- M.C. da Silva, M.M. Silva, F.S. Reis, A.L.T.G. Ruiz, J.E. de Carvalho, J.C.C. Santos, I.M. Figueiredo, R.B. Alves, L.V. Modolo and Â. de Fátima, J. Photochem. Photobiol. B, 172, 129 (2017); https://doi.org/10.1016/j.jphotobiol.2017.05.020.
- P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski and F. Bartl, Curr. Org. Chem., 13, 124 (2009); https://doi.org/10.2174/138527209787193774.
- L. Shi, H.M. Ge, S.H. Tan, H.Q. Li, Y.C. Song, H.L. Zhu and R.-X. Tan, Eur. J. Med. Chem., 42, 558 (2007); https://doi.org/10.1016/j.ejmech.2006.11.010.
- S.N. Pandeya, D. Sriram, G. Nath and E. de Clercq, Farmaco, 54, 624 (1999); https://doi.org/10.1016/S0014-827X(99)00075-0.
- M.S. Karthikeyan, D.J. Prasad, B. Poojary, K. Subrahmanya Bhat, B.S. Holla and N.S. Kumari, Bioorg. Med. Chem., 14, 7482 (2006); https://doi.org/10.1016/j.bmc.2006.07.015.
- A. Echevarria, M.G. Nascimento, V. Geronimo, J. Miller and A. Giesbrecht, J. Braz. Chem. Soc., 10, 60 (1999); https://doi.org/10.1590/S0103-50531999000100010.
- H.-M. Kuo, W.-P. Ko, G.-H. Lee and C.K. Lai, Tetrahedron, 72, 6321 (2016); https://doi.org/10.1016/j.tet.2016.07.076.
- A.O. de Souza, F.C.S. Galetti, C.L. Silva, B. Bicalho, M.M. Parma and S.F. Fonseca, A.J. Marsaioli, A.C.L.B. Trindade, R.P. Freitas Gil, F.S. Bezerra, M. Andrade-Neto and M.C.F. de Oliveira, Quim. Nova, 30, 1563 (2007); https://doi.org/10.1590/S0100-40422007000700012.
- Z. Guo, R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang and P. Li, Carbohydr. Res., 342, 1329 (2007); https://doi.org/10.1016/j.carres.2007.04.006.
- N. Mulcahy, Medical News, Cancer to Become Leading Cause of Death Worldwide by 2010, 10 December (2008).
- J.S. Driscoll, G.F. Hazard, H.B. Wood and A. Goldin, Cancer Chemother. Rep., 4, 1 (1974).
- M.-F. Zaltariov, M. Avadanei, M. Balan, D. Peptanariu, N. Vornicu and S. Shova, J. Mol. Struct., 1175, 624 (2019); https://doi.org/10.1016/j.molstruc.2018.08.019.
- K.C. Liu, J. Li and S. Sakya, Mini Rev. Med. Chem., 4, 1105 (2004); https://doi.org/10.2174/1389557043402900.
- R.S. Thirumurugan, S. Kavimani and R.S. Srivastava, Biol. Pharm. Bull., 23, 1438 (2000); https://doi.org/10.1248/bpb.23.1438.
- P. Siripong, K. Kanokmedakul, S. Piyaviriyakul, J. Yahuafai, R. Chanpai, S. Ruchirawat and N. Oku, J. Trad. Med., 23, 166 (2006); https://doi.org/10.11339/jtm.23.166.
- P. Siripong, C. Hahnvajanawong, S. Piyaviriyakul, K. Kanokmedhakul, J. Yahuafai, N. Kongkathip, S. Ruchirawat and N. Oku, Biol. Pharm. Bull., 32, 1251 (2009); https://doi.org/10.1248/bpb.32.1251.
- N. Kongkathip, B. Kongkathip, P. Siripong, C. Sangma, S. Luangkamin, M. Niyomdecha, S. Pattanapa, S. Piyaviriyagul and P. Kongsaeree, Bioorg. Med. Chem., 11, 3179 (2003); https://doi.org/10.1016/S0968-0896(03)00226-8.
- M. Dubin, S.H. Villamil Fernandez and A.O. Stoppani, Medicina (Buenos Aires), 61, 343 (2001).
- C.C. Lai, T.J. Liu, L.K. Ho, M.J. Don and Y.P. Chau, Histol. Histopathol., 13, 89 (1998).
- G. Elmaci, H. Duyar, B. Aydiner, N. Seferoglu, M.A. Naziri, E. Sahin and Z. Seferoglu, J. Mol. Struct., 1162, 37 (2018); https://doi.org/10.1016/j.molstruc.2018.02.035.
- A.B. Pardee, Y.Z. Li and C.J. Li, Curr. Cancer Drug Targets, 2, 227 (2002); https://doi.org/10.2174/1568009023333854.
- D. Wang, M.Y. Xia, Z. Cui, S. Tashiro, S. Onodera and T. Ikejima, Biol. Pharm. Bull., 27, 1025 (2004); https://doi.org/10.1248/bpb.27.1025.
- J. Chen, Y.W. Huang, G. Liu, Z. Afrasiabi, E. Sinn, S. Padhye and Y. Ma, Toxicol. Appl. Pharmacol., 197, 40 (2004); https://doi.org/10.1016/j.taap.2004.02.004.
- Z. Afrasiabi, E. Sinn, J. Chen, Y. Ma, A.L. Rheingold, L.N. Zakharov, N. Rath and S. Padhye, Inorg. Chim. Acta, 357, 271 (2004); https://doi.org/10.1016/S0020-1693(03)00484-5.
- S. Shukla, R.S. Srivastava, S.K. Shrivastava, A. Sodhi and P. Kumar, Appl. Biochem. Biotechnol., 167, 1430 (2012); https://doi.org/10.1007/s12010-012-9551-9.
- G.Q. Hu, L.L. Hou, S.Q. Xie and W.L. Huang, Chin. J. Chem., 26, 1145 (2008); https://doi.org/10.1002/cjoc.200890205.
- P. Pathak, V.S. Jolly and K.P. Sharma, Orient. J. Chem., 16, 493 (2000).
- L. Touafri, A. Hellal, S. Chafaa, A. Khelifa and A. Kadri, J. Mol. Struct., 1149, 750 (2017); https://doi.org/10.1016/j.molstruc.2017.08.052.
- B.J. McConkey, V. Sobolev and M. Edelman, Curr. Sci., 83, 845 (2002).
- L.J. McGaw, E.E. Elgorash and J.N. Eloff, ed.: V. Kuete, Cytotoxicity of African Medicinal Plants Against Normal Animal and Human Cells, In: Toxicological Survey of African Medicinal Plants, Elsevier, Chap. pp. 181-233 (2014).
References
W. Al Zoubi, Int. J. Org. Chem., 3, Article ID: 40184 (2013); https://doi.org/10.4236/ijoc.2013.33A008.
G. Bringmann, M. Dreyer, J.H. Faber, P.W. Dalsgaard, J.W. Jaroszewski, H. Ndangalasi, F. Mbago, R. Brun and S.B. Christensen, J. Nat. Prod., 67, 743 (2004); https://doi.org/10.1021/np0340549.
E. Horak, P. Kassal, M. Hranjec and I.M. Steinberg, Sens. Actuators B Chem., 258, 415 (2018); https://doi.org/10.1016/j.snb.2017.11.121.
P. Rathelot, P. Vanelle, M. Gasquet, F. Delmas, M.P. Crozet, P. TimonDavid and J. Maldonado, Eur. J. Med. Chem., 30, 503 (1995); https://doi.org/10.1016/0223-5234(96)88261-4.
A.A. Shanty, J.E. Philip, E.J. Sneha, M.R.P. Kurup, S. Balachandran and P.V. Mohanan, Bioorg. Chem., 70, 67 (2017). https://doi.org/10.1016/j.bioorg.2016.11.009.
M.C. da Silva, M.M. Silva, F.S. Reis, A.L.T.G. Ruiz, J.E. de Carvalho, J.C.C. Santos, I.M. Figueiredo, R.B. Alves, L.V. Modolo and Â. de Fátima, J. Photochem. Photobiol. B, 172, 129 (2017); https://doi.org/10.1016/j.jphotobiol.2017.05.020.
P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski and F. Bartl, Curr. Org. Chem., 13, 124 (2009); https://doi.org/10.2174/138527209787193774.
L. Shi, H.M. Ge, S.H. Tan, H.Q. Li, Y.C. Song, H.L. Zhu and R.-X. Tan, Eur. J. Med. Chem., 42, 558 (2007); https://doi.org/10.1016/j.ejmech.2006.11.010.
S.N. Pandeya, D. Sriram, G. Nath and E. de Clercq, Farmaco, 54, 624 (1999); https://doi.org/10.1016/S0014-827X(99)00075-0.
M.S. Karthikeyan, D.J. Prasad, B. Poojary, K. Subrahmanya Bhat, B.S. Holla and N.S. Kumari, Bioorg. Med. Chem., 14, 7482 (2006); https://doi.org/10.1016/j.bmc.2006.07.015.
A. Echevarria, M.G. Nascimento, V. Geronimo, J. Miller and A. Giesbrecht, J. Braz. Chem. Soc., 10, 60 (1999); https://doi.org/10.1590/S0103-50531999000100010.
H.-M. Kuo, W.-P. Ko, G.-H. Lee and C.K. Lai, Tetrahedron, 72, 6321 (2016); https://doi.org/10.1016/j.tet.2016.07.076.
A.O. de Souza, F.C.S. Galetti, C.L. Silva, B. Bicalho, M.M. Parma and S.F. Fonseca, A.J. Marsaioli, A.C.L.B. Trindade, R.P. Freitas Gil, F.S. Bezerra, M. Andrade-Neto and M.C.F. de Oliveira, Quim. Nova, 30, 1563 (2007); https://doi.org/10.1590/S0100-40422007000700012.
Z. Guo, R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang and P. Li, Carbohydr. Res., 342, 1329 (2007); https://doi.org/10.1016/j.carres.2007.04.006.
N. Mulcahy, Medical News, Cancer to Become Leading Cause of Death Worldwide by 2010, 10 December (2008).
J.S. Driscoll, G.F. Hazard, H.B. Wood and A. Goldin, Cancer Chemother. Rep., 4, 1 (1974).
M.-F. Zaltariov, M. Avadanei, M. Balan, D. Peptanariu, N. Vornicu and S. Shova, J. Mol. Struct., 1175, 624 (2019); https://doi.org/10.1016/j.molstruc.2018.08.019.
K.C. Liu, J. Li and S. Sakya, Mini Rev. Med. Chem., 4, 1105 (2004); https://doi.org/10.2174/1389557043402900.
R.S. Thirumurugan, S. Kavimani and R.S. Srivastava, Biol. Pharm. Bull., 23, 1438 (2000); https://doi.org/10.1248/bpb.23.1438.
P. Siripong, K. Kanokmedakul, S. Piyaviriyakul, J. Yahuafai, R. Chanpai, S. Ruchirawat and N. Oku, J. Trad. Med., 23, 166 (2006); https://doi.org/10.11339/jtm.23.166.
P. Siripong, C. Hahnvajanawong, S. Piyaviriyakul, K. Kanokmedhakul, J. Yahuafai, N. Kongkathip, S. Ruchirawat and N. Oku, Biol. Pharm. Bull., 32, 1251 (2009); https://doi.org/10.1248/bpb.32.1251.
N. Kongkathip, B. Kongkathip, P. Siripong, C. Sangma, S. Luangkamin, M. Niyomdecha, S. Pattanapa, S. Piyaviriyagul and P. Kongsaeree, Bioorg. Med. Chem., 11, 3179 (2003); https://doi.org/10.1016/S0968-0896(03)00226-8.
M. Dubin, S.H. Villamil Fernandez and A.O. Stoppani, Medicina (Buenos Aires), 61, 343 (2001).
C.C. Lai, T.J. Liu, L.K. Ho, M.J. Don and Y.P. Chau, Histol. Histopathol., 13, 89 (1998).
G. Elmaci, H. Duyar, B. Aydiner, N. Seferoglu, M.A. Naziri, E. Sahin and Z. Seferoglu, J. Mol. Struct., 1162, 37 (2018); https://doi.org/10.1016/j.molstruc.2018.02.035.
A.B. Pardee, Y.Z. Li and C.J. Li, Curr. Cancer Drug Targets, 2, 227 (2002); https://doi.org/10.2174/1568009023333854.
D. Wang, M.Y. Xia, Z. Cui, S. Tashiro, S. Onodera and T. Ikejima, Biol. Pharm. Bull., 27, 1025 (2004); https://doi.org/10.1248/bpb.27.1025.
J. Chen, Y.W. Huang, G. Liu, Z. Afrasiabi, E. Sinn, S. Padhye and Y. Ma, Toxicol. Appl. Pharmacol., 197, 40 (2004); https://doi.org/10.1016/j.taap.2004.02.004.
Z. Afrasiabi, E. Sinn, J. Chen, Y. Ma, A.L. Rheingold, L.N. Zakharov, N. Rath and S. Padhye, Inorg. Chim. Acta, 357, 271 (2004); https://doi.org/10.1016/S0020-1693(03)00484-5.
S. Shukla, R.S. Srivastava, S.K. Shrivastava, A. Sodhi and P. Kumar, Appl. Biochem. Biotechnol., 167, 1430 (2012); https://doi.org/10.1007/s12010-012-9551-9.
G.Q. Hu, L.L. Hou, S.Q. Xie and W.L. Huang, Chin. J. Chem., 26, 1145 (2008); https://doi.org/10.1002/cjoc.200890205.
P. Pathak, V.S. Jolly and K.P. Sharma, Orient. J. Chem., 16, 493 (2000).
L. Touafri, A. Hellal, S. Chafaa, A. Khelifa and A. Kadri, J. Mol. Struct., 1149, 750 (2017); https://doi.org/10.1016/j.molstruc.2017.08.052.
B.J. McConkey, V. Sobolev and M. Edelman, Curr. Sci., 83, 845 (2002).
L.J. McGaw, E.E. Elgorash and J.N. Eloff, ed.: V. Kuete, Cytotoxicity of African Medicinal Plants Against Normal Animal and Human Cells, In: Toxicological Survey of African Medicinal Plants, Elsevier, Chap. pp. 181-233 (2014).