5-(4-Methoxybenzylidene)thiazolidine-2,4-dione-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations.
Antineoplastic Agents
/ chemical synthesis
Doxorubicin
/ pharmacology
HCT116 Cells
Hep G2 Cells
Humans
Inhibitory Concentration 50
MCF-7 Cells
Molecular Docking Simulation
Neoplasms
/ drug therapy
Protein Kinase Inhibitors
/ chemical synthesis
Sorafenib
/ pharmacology
Structure-Activity Relationship
Thiazolidinediones
/ chemical synthesis
Vascular Endothelial Growth Factor Receptor-2
/ antagonists & inhibitors
VEGFR-2 inhibitors
anticancer agents
molecular docking
thiazolidine-2,4-dione
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
Sep 2020
Sep 2020
Historique:
received:
17
03
2020
revised:
11
05
2020
accepted:
14
05
2020
pubmed:
10
6
2020
medline:
11
6
2021
entrez:
10
6
2020
Statut:
ppublish
Résumé
A novel series of 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives, 5a-g and 7a-f, was designed, synthesized, and evaluated for their anticancer activity against HepG2, HCT116, and MCF-7 cells. HepG2 and HCT116 were the most sensitive cell lines to the influence of the new derivatives. In particular, compounds 7f, 7e, 7d, and 7c were found to be the most potent derivatives of all the tested compounds against the HepG2, HCT116, and MCF-7 cancer cell lines. Compound 7f (IC
Identifiants
pubmed: 32515896
doi: 10.1002/ardp.202000079
doi:
Substances chimiques
5-(4-methoxybenzylidene)thiazolidine-2,4-dione
0
Antineoplastic Agents
0
Protein Kinase Inhibitors
0
Thiazolidinediones
0
Doxorubicin
80168379AG
Sorafenib
9ZOQ3TZI87
KDR protein, human
EC 2.7.10.1
Vascular Endothelial Growth Factor Receptor-2
EC 2.7.10.1
Types de publication
Comparative Study
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000079Informations de copyright
© 2020 Deutsche Pharmazeutische Gesellschaft.
Références
G. Gasparini, R. Longo, M. Toi, N. Ferrara, Nat. Clin. Pract. Oncol. 2005, 2, 562.
M. Potente, H. Gerhardt, P. Carmeliet, Cell 2011, 146, 873.
L. Qin, J. L. Bromberg-White, C. N. Qian, Adv. Cancer Res. 2012, 113, 191.
A. Bishayee, A. S. Darvesh, Curr. Cancer Drug Targets 2012, 12, 1095.
R. S. Kerbel, N. Engl. J. Med. 2008, 358, 2039.
M. Shibuya, Genes Cancer 2011, 2, 1097.
H. C. Spangenberg, R. Thimme, H. E. Blum, Nat. Rev. Gastroenterol. Hepatol. 2009, 6, 423.
N. Ferrara, H. P. Gerber, J. LeCouter, Nat. Med. 2003, 9, 669.
S. Koch, S. Tugues, X. Li, L. Gualandi, L. Claesson-Welsh, Biochem. J. 2011, 437, 169.
H. Joshi, T. Pal, C. S. Ramaa, Expert Opin. Investig. Drugs 2014, 23, 501. https://doi.org/10.1517/13543784.2014.884708
U. Bhanushali, S. Rajendran, K. Sarma, P. Kulkarni, K. Chatti, S. Chatterjee, C. S. Ramaa, Bioorg. Chem. 2016, 67, 139. https://doi.org/10.1016/j.bioorg.2016.06.006
D. K. Shah, K. M. Menon, L. M. Cabrera, A. Vahratian, S. K. Kavoussi, D. I. Lebovic, Fertil. Steril. 2010, 93, 2042. https://doi.org/10.1016/j.fertnstert.2009.02.059
L. Nagarapu, B. Yadagiri, R. Bantu, C. G. Kumar, S. Pombala, J. Nanubolu, Eur. J. Med. Chem. 2014, 71, 91.
Y. M. Ha, Y. J. Park, J. A. Kim, D. Park, J. Y. Park, H. J. Lee, J. Y. Lee, H. R. Moon, H. Y. Chung, Eur. J. Med. Chem. 2012, 49, 245.
S. Faivre, C. Delbaldo, K. Vera, C. Robert, S. Lozahic, N. Lassau, C. Bello, S. Deprimo, N. Brega, G. Massimini, J. P. Armand, P. Scigalla, E. Raymond, J. Clin. Oncol. 2006, 24, 25.
Q. Li, A. Al-Ayoubi, T. Guo, H. Zheng, A. Sarkar, T. Nguyen, S. T. Eblen, S. Grant, G. E. Kellogg, S. Zhang, Bioorg. Med. Chem. Lett. 2009, 19, 6042.
R. Romagnoli, P. G. Baraldi, M. K. Salvador, M. E. Camacho, J. Balzarini, J. Bermejo, F. Estévez, Eur. J. Med. Chem. 2013, 63, 544. https://doi.org/10.1016/j.ejmech.2013.02.030
C. Nastasă, R. Tamaian, O. Oniga, B. Tiperciuc, Medicina 2019, 55, 1.
S. Takahashi, Biol. Pharm. Bull. 2011, 34, 1785.
J. Kankanala, A. M. Latham, A. P. Johnson, S. Homer-Vanniasinkam, C. W. Fishwick, S. Ponnambalam, Br. J. Pharmacol. 2012, 166, 737.
P. Wu, T. E. Nielsen, M. H. Clausen, Trends Pharmacol. Sci. 2015, 36, 422.
S. Wilhelm, C. Carter, M. Lynch, T. Lowinger, J. Dumas, R. A. Smith, B. Schwartz, R. Simantov, S. Kelley, Nat. Rev. Drug Discov. 2006, 5, 835.
A. Pircher, W. Hilbe, I. Heidegger, J. Drevs, A. Tichelli, M. Medinger, Int. J. Mol. Sci. 2011, 12, 7077. https://doi.org/10.3390/ijms12107077
Q.-Q. Xie, H.-Z. Xie, J.-X. Ren, L.-L. Li, S.-Y. Yang, J. Mol. Graph. Model. 2009, 27, 751.
K. Lee, K.-W. Jeong, Y. Lee, J. Y. Song, M. S. Kim, G. S. Lee, Y. Kim, Eur. J. Med. Chem. 2010, 45, 542.
R. N. Eskander, K. S. Tewari, Gynecol. Oncol. 2014, 132, 496.
V. A. Machado, D. Peixoto, R. Costa, H. J. Froufe, R. C. Calhelha, R. M. Abreu, I. C. Ferreira, R. Soares, M.-J. R. Queiroz, Bioorg. Med. Chem. 2015, 23, 6497.
J. Dietrich, C. Hulme, L. H. Hurley, Bioorg. Med. Chem. 2010, 18, 5738.
A. Garofalo, L. Goossens, P. Six, A. Lemoine, S. Ravez, A. Farce, P. Depreux, Bioorg. Med. Chem. Lett. 2011, 21, 2106.
M. A. Aziz, R. A. Serya, D. S. Lasheen, A. K. Abdel-Aziz, A. Esmat, A. M. Mansour, A. N. B. Singab, K. A. Abouzid, Sci. Rep. 2016, 6, 1. https://doi.org/10.1038/srep24460
L. Zhang, Y. Shan, X. Ji, M. Zhu, C. Li, Y. Sun, R. Si, X. Pan, J. Wang, W. Ma, B. Dai, B. Wang, J. Zhang, Oncotarget 2017, 8, 104745. https://doi.org/10.18632/oncotarget.20065
C. Viegas-Junior, A. Danuello, V. da Silva Bolzani, E. J. Barreiro, C. A. M. Fraga, Curr. Med. Chem. 2007, 14, 1829.
A. A. El-Helby, R. R. A. Ayyad, H. Sakr, K. El-Adl, M. M. Ali, F. Khedr, Arch. Pharm. Chem. Life Sci. 2017, 350, e201700240. https://doi.org/10.1002/ardp.201700240
A. A. El-Helby, H. Sakr, R. R. A. Ayyad, K. El-Adl, M. M. Ali, F. Khedr, Anti-Cancer Agents in Med. Chem. 2018, 18, 1. https://doi.org/10.2174/1871520618666180412123833
S. A. Starosyla, G. P. Volynets, V. G. Bdzhola, A. G. Golub, S. M. Yarmoluk, World. J. Pharmacol. 2014, 3, 162.
Z. Gagic, D. Ruzic, N. Djokovic, T. Djikic, K. Nikolic, Front. Chem. 2020, 7, 1.
A. A. El-Helby, H. Sakr, I. H. Eissa, H. Abulkhair, A. A. Al-Karmalawy, K. El-Adl, Arch. Pharm. Chem. Life Sci. 2019, 352, e201900113. https://doi.org/10.1002/ardp.201900113
A. A. El-Helby, H. Sakr, I. H. Eissa, A. A. Al-Karmalawy, K. El-Adl, Arch. Pharm. Chem. Life Sci. 2019, 352, e201900178. https://doi.org/10.1002/ardp.201900178
Sucheta, S. Tahlan, P. K. Verma, Chem. Cent. J. 2017, 11, 130.
R. S. Bahare, S. Ganguly, K. Choowongkomon, S. Seetaha, DARU J. Pharm. Sci. 2015, 23, 1.
S. A. H. El-Feky, H. A. Abd El-Fattah, N. A. Osman, M. Imran, M. N. Zedan, J. Chem. Pharm. Res. 2015, 7, 1154.
B. Baum, M. Mohamed, M. Zayed, C. Gerlach, A. Heine, D. Hangauer, G. Klebe, J. Mol. Biol. 2009, 390, 56.
L. Englert, A. Biela, M. Zayed, A. Heine, D. Hangauer, G. Klebe, Biochim. Biophys. Acta 2010, 1800, 1192.
A. A. El-Helby, R. R. A. Ayyad, K. El-Adl, H. Sakr, A. A. Abd-Elrahman, I. H. Eissa, A. Elwan, Med. Chem. Res. 2016, 25, 3030.
A. A. El-Helby, R. R. A. Ayyad, K. El-Adl, A. Elwan, Med. Chem. Res. 2017, 26, 2967.
A. A. El-Helby, R. R. A. Ayyad, M. F. Zayed, H. S. Abulkhair, H. Elkady, K. El-Adl, Arch. Pharm. Chem. Life Sci. 2019, 352, e201800387. https://doi.org/10.1002/ardp.201800387
A. A. El-Helby, R. R. A. Ayyad, H. Elkady, K. El-Adl, Mol. Divers. 2019, 23, 283. https://doi.org/10.1007/s11030-018-9871-y
T. Mosmann, J. Immunol. Methods 1983, 65, 55.
D. A. Scudiero, R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Nofziger, M. J. Currens, D. Seniff, M. R. Boyd, Cancer Res. 1988, 48, 4827.
F. M. Freimoser, C. A. Jakob, M. Aebi, U. Tuor, Appl. Environ. Microbiol. 1999, 65, 3727.
A. Mishra, G. V. Ghanshyam, B. Singh, J. Sweemit, S. Kumar, Int. J. Pharm. Sci. Res. 2010, 1, 41.
A. A. El-Helby, R. R. Ayyad, H. M. Sakr, A. S. Abdelrahim, K. El-Adl, F. S. Sherbiny, I. H. Eissa, M. M. Khalifa, J. Mol. Struct. 2017, 1130, 333.
S. A. Katke, S. V. Amrutkar, R. J. Bhor, M. V. Khairnar, Int. J. Pharm. Sci. Res. 2011, 2, 148.
D. C. P. Singh, S. R. Hashim, R. G. Singhal, J. Chem. 2011, 8, 635.
F. M. Chen, N. L. Benoiton, Can. J. Chem. 1987, 65, 619.
S. M. Abou-Seri, W. M. Eldehna, M. M. Ali, D. A. Abou El Ella, Eur. J. Med. Chem. 2016, 107, 165. https://doi.org/10.1016/j.ejmech.2015.10.053