Synthesis and cytotoxicity evaluation of [(2,4-dichlorophenoxy)methyl]-5-aryl-1,3,4-oxadiazole/4 H -1,2,4-triazole analogues
We report herein the synthesis, characterization, and cytotoxicity
evaluations of some newer oxadiazole and triazole analogues
(5a-j). The cytotoxicity of all the title compounds were
evaluated as per the National Cancer Institute protocol in a one-dose assay
(10 μμ\mu M) on nine different panels of 59 cancer cell lines.
2-{{\{5-[(2,4-Dichlorophenoxy)methyl]-1,3,4-oxadiazol-2-yl}}\}phenol
(5e) showed the maximum cytotoxicity among the series of ten
compounds. The cytotoxicity of 5e was comparable to that of the
standard anticancer drug, 5-fluorouracil, and better than that of imatinib.
The structure activity relationship was also discussed.
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- Siegel, R. L.; Miller, K. D.; Jemal, A.
CA Cancer J. Clin
.
2017
,
67
, 7-30.
- Siegel, R. L.; Miller, K. D.; Jemal, A.
CA Cancer J. Clin
.
2018
,
68
, 7-30.
- Arruebo, M.; Vilaboa, N.; Saez-Gutierrez, B.; Lambea, J.; Tres, A.; Valladares, M.; Gonzalez-Fernandez, A.
Cancers
2011
,
3
, 3279-3330.
- Aydemir, N.; Bilaloglu, R. Genotoxicity of two anticancer drugs, gemcitabine and topotecan, in mouse bone marrow
in vivo.
Mutat
.
Res
.
2003
,
537
, 43-51.
- Bostrom, A.; Hogner, A.; Llinas, A.; Wellner, E.; Plowright, A. T.
J. Med. Chem
.
2012
,
55
, 1817-1830.
- Ahsan, M. J.; Samy, G. J.; Habibullah, K.; Nomani, M. S.; Saraswat, P.; Gaur, R.; Singh, A.
Bioorg. Med. Chem.
Lett.
2011
,
21
, 7246-7250.
- Zhang, K.; Wang, P.; Xuan, L.; Fu, X.; Jing, F.; Li, S,; Liu, Y.; Chen, B.
Bioorg. Med. Chem. Lett
.
2014
,
24
,
5154-5156.
- Khan, M. U.; Akhtar, T.; Al-Masoudi, N. A.; Stoeckli-Evans, H.; Hameed, S.
Med. Chem.
2012
,
8
, 1190-1197.
- Jones, R. M.; Leonard, J. N.; Buzard, D. J.; Lehmann, J.
Expert Opin. Ther. Pat
.
2009
,
19
, 1339-1359.
- Lee, S. H.; Seo, H. J.; Lee, S. H.; Jung, M. E.; Park, J. H.; Park, H. J.; Yoo, J.; Yun, H.; Na, J.; Kang, S. Y.; et
al
. Med. Chem
.
2008
,
51
, 7216-7233.
- Rathore, A.; Sudhakar, R.; Ahsan, M. J.; Ali, A.; Subbarao, N.; Jadav, S. S.; Umar, S.; ShaharYar, M.
Bioorg.
Chem
.
2017
,
70
, 107-117.
- Sangshetti, J. N.; Chabukswar, A. R.; Shinde, B.
Bioorg. Med. Chem. Lett.
2011
,
21
, 444-448.
- Patani, G. A.; LaVoie, E. J.
Chem. Rev
.
1996
,
96
, 3147-3176.
- Warmus, J. S.; Flamme, C.; Zhang, L. Y.; Barrrett, S.; Bridges, A.; Kaufman, M.; Tecle, H.; Gowan, R.; Sebolt-
Leopold, J.; Leopold, W.; et al.
Bioorg. Med. Chem. Lett
.
2008
,
18
, 6171-6174.
- McBriar, M. D.; Clader, J. W.; Chu, I.; Del Vecchio, R. A.; Favreau, L.; Greenlee, W. J.; Hyde, L. A.; Nomeir, A.
A.; Parker, E. M.; Pissarnitski, D. A.; et al.
Bioorg. Med. Chem. Lett
.
2008
,
18
, 215-219.
- Ouyang, X.; Chen, X.; Piatnitski, E. L.; Kiselyov, A. S.; He, H. Y.; Mao, Y.; Pattaropong, V.; Yu, Y.; Kim, K.
H.; Kincaid, J.; et al.
Bioorg. Med. Chem. Lett
.
2005
,
15
, 5154-9.
- Kaur, R.; Dwivedi, A. R.; Kumar, B.; Kumar, V.
Anticancer Agents Med. Chem
.
2016
,
16
, 465-489.
- Ahsan, M. J.; Choupra, A.; Sharma, R. K.; Jadav, S. S.; Hassan, M. Z.; Bakht, M. A.; Padmaja, P.; Al-Tamini,
A. B. S.; Geesi, M. H.
Anticancer Agents Med. Chem
.
2017
,
18
, 121-138.
- Ahsan, M. J.; Ansari, M. Y.; Kumar, P.; Soni, M.; Yasmin, S.; Jadav, S. S.; Sahoo, G. C.
Beni-Seuf Univ. J. Basic
Appl Sci
.
2016
,
5
, 119-125.
- Yeung, K. S.; Farkas, M. E.; Kadow, J. F.; Meanwell, N. A.
Tetrahedron Lett
.
2005
,
46
, 3429-3432.
- Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney,
S.; Boyd, M. R.
J. Natl. Cancer Inst
.
1990
,
83
, 1107-11012.
- Boyd, M. R.; Paull, K. D.
Drug Dev. Res.
,
1995
,
34
, 91-109.
- Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.;
Vaigro-Wolff, A.; et al.
J. Nat. Cancer Inst.
1991
,
83
, 757-766.
- Shoemaker, R. H.
Nat. Rev. Cancer
2006
,
6
, 813-823.
- Corona, P.; Carta, A.; Loriga, M.; Vitale, G.; Paglietti, G.
Eur. J. Med. Chem
.
2009
,
44
, 1579-1591.