SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 3: 731 - 739

DOI: https://doi.org/10.6023/cjoc201907052

Design, Synthesis and Biological Activities of Compounds Containing 1,3,4-Oxadiazole or 1,3,4-Thiadiazole

  • Yan Longjia ,
  • Li Yongliang ,
  • Deng Minggao ,
  • Chen Anchao ,
  • Du Zhiyun ,
  • Dong Changzhi ,
  • Chen Huixiong
Expand
  • a Faculty of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou, 510006, China;
    b Biomédicale, Université Paris Descartes, 75006 Paris, France;
    c Université Paris Diderot, 75013 Paris, France

Received date: 2019-07-30

  Revised date: 2019-09-21

  Online published: 2020-04-02

Supported by

Project supported by the National Natural Science Foundation of China (No. 21672043).

Fold

Abstract

In order to find new anti-tumor drugs, a series of novel 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives were designed and synthesized. The target compounds were evaluated for antitumor activity in vitro on four human cancer cell lines including B-16 (skin melanoma cells), PC-3 (human prostate cancer cells), U87 (human primary glioblastoma cells) and A549 (human non-small cell lung cancer cells). The results displayed that some of the compounds had good activities, especially, 5-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-N-(2-methoxyphenyl)-1,3,4-thiadiazole-2-carboxamide (8b) and 5-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-N-(4-methoxyphenyl)-1,3,4-thiadiazole-2-carboxamide (8c) showed high antitumor activities against four cancer cell lines, which was better than dasatinib. These compounds were further studied for their possible target of tumor suppression.

Key words： 1,3,4-oxadiazole; 1,3,4-thiadiazole; anti-cancer; Src inhibitor

Cite this article

Yan Longjia , Li Yongliang , Deng Minggao , Chen Anchao , Du Zhiyun , Dong Changzhi , Chen Huixiong . Design, Synthesis and Biological Activities of Compounds Containing 1,3,4-Oxadiazole or 1,3,4-Thiadiazole[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 731 -739 . DOI: 10.6023/cjoc201907052

References

[1] Majumdar, P.; Pati, A.; Patra, M.; Behera, R.; Behera, A. K. Chem. Rev. 2014, 114, 2942.
[2] Guin, S.; Ghosh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett. 2011, 13, 5976.
[3] Khalilullah, H.; Ahsan, M. J.; Hedaitullah, M.; Khan, S.; Ahmed, B. Mini-Rev. Med. Chem. 2012, 12, 789.
[4] Fathi, M. A. A.; Abd, Ei-Hafeez, A. A.; Abdelhamid, D.; Abbas, S. H.; Montano, M. M.; Abdel-Aziz, M. Bioorg. Chem. 2019, 84, 150.
[5] Huang, W. S.; Metcalf, C. A.; Sundaramoorthi, R.; Wang, Y.; Zou, D.; Thomas, R. M.; Zhu, X.; Cai, L.; Wen, D.; Liu, S.; Romero, J.; Qi, J.; Chen, I.; Banda, G.; Lentini, S. P.; Das, S.; Xu, Q.; Keats, J.; Wang, F.; Wardwell, S.; Ning, Y.; Snodgrass, J. T.; Broudy, M. I.; Russian, K.; Zhou, T.; Commodore, L.; Narasimhan, N. I.; Mohemmad, Q. K.; Iuliucci, J.; Rivera, V. M.; Dalgamo, D. C.; Sawyer, T. K.; Clackson, T.; Shakespeare, W. C. J. Med. Chem. 2010, 53, 4701.
[6] Summa, V.; Petrocchi, A.; Bonelli, F.; Crescenzi, B.; Donghi, M.; Ferrara, M.; Fiore, F.; Gardelli, C.; Gonzalez, Paz. O.; Hazuda, D. J.; Jones, P.; Kinzel, O.; Laufer, R.; Monteagudo, E.; Muraglia, E.; Nizi, E.; Orvieto, F.; Pace, P.; Pescatore, G.; Scarpelli, R.; Stillmock, K.; Witmer, M. V.; Rowley, M. J. Med. Chem. 2008, 51, 5843.
[7] Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. J. Med. Chem. 2005, 48, 7860.
[8] Nishimori, I.; Minakuchi, T.; Morimoto, K.; Sano, S.; Onishi, S.; Takeuchi, H.; Vullo, D.; Scozzafava, A.; Supuran, C. T. J. Med. Chem. 2006, 49, 2117.
[9] Tian, K.; Meng, J.; Gan, Y.; Li, X.; Wu, S.; Chen, J.; Li, W.; Qi, Y.; Hu, W.; Wang, Z.; Ouyang, G. Chin. J. Org. Chem. 2018, 38, 2657(in Chinese). (田坤, 孟娇, 甘宜远, 李小琴, 巫受群, 陈洁, 李文, 漆亚云, 胡伟男, 王贞超, 欧阳贵平, 有机化学, 2018, 38, 2657.)
[10] Fathi, M. A. A.; Ei-Hafeez, A. A. A.; Abdelhamid, D.; Abbas, S. H.; Montano, M. M.; Abdel-Aziz, M. Bioorg. Chem. 2019, 84, 150.
[11] Radi, M.; Crespan, E.; Lalchi, F.; Bernardo, V.; Zanoli, S.; Manetti, F.; Schenone, S.; Maga, G.; Botta, M. ChemMedChem 2010, 5, 1226.
[12] Hu, Y.; Li, C. Y.; Wang, X. M.; Yang, Y. H.; Zhu, H. L. Chem. Rev. 2014, 114, 5572.
[13] Yang, J.; Che, X.; Dang, Q.; Wei, Z.; Gao, S.; Bai, X. Org. Lett. 2005, 7, 1541.
[14] Campiotti, L.; Suter, M. B.; Guasti, L.; Piazza, R.; Gambacorti-Passerini, C.; Grandi, A. M.; Squizzato, A. Eur. J. Cancer 2017, 77, 48.
[15] Das, J.; Chen, P.; Norris, D.; Padmanabha, R.; Lin, J.; Moquin, R. V.; Shen, Z.; Cook, L. S.; Doweyko, A. M.; Pitt, S.; Pang, S.; Shen, D. R.; Fang, Q.; de Fex, H. F.; McIntyre, K. W.; Shuster, D. J.; Gillooly, K. M.; Behnia, K.; Schieven, G. L.; Wityak, J.; Barrish, J. C. J. Med. Chem. 2006, 49, 6819.
[16] Chai, X. X.; Cai, Z. P.; Yang, M. T.; Zhou, Y.; Fu, Y. J.; Xiong, Y. Z. Arch. Pharm. 2016, 349, 1.
[17] Shi, L.; Xu, J.; Bi, J.; Zhang, Z.; Liu, T.; Yang, X.; Zhang, G. Chin. J. Org. Chem. 2018, 38, 3016(in Chinese). (时蕾, 徐晶晶, 毕晶晶, 张志国, 刘统信, 杨晓岚, 张贵生, 有机化学, 2018, 38, 3016.)
[18] Yan, L.; Deng, M.; Chen, A.; Li, Y.; Zhang, W.; Du, Z.; Dong, C.; Meunier, B.; Chen, H. Tetrahedron Lett. 2019, 60, 1359.
[19] Novak, A.; Humphreys, L. D.; Walker, M. D.; Woodward, S. Tetrahedron Lett. 2006, 47, 5767.
[20] Jacobs, C.; Rubsamen, H. Cancer Res. 1983, 43, 1696.
[21] Roskoski, R. J. Pharmacol. Res. 2015, 94, 9.
Options
Outlines

/

〈 〉