Citation: Liu Tingting, Wan Yichao, Fang Hao. Synthesis and Antiproliferative Activity of Novel 1,3,4-Thiadiazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 417-424. doi: 10.6023/cjoc201507038 shu

Synthesis and Antiproliferative Activity of Novel 1,3,4-Thiadiazole Derivatives

1.
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Ji'nan 250012

Corresponding author: Fang Hao,
Received Date: 29 July 2015
Available Online: 13 September 2015

Twenty eight novel 1,3,4-thiadiazole derivatives were synthesized using different phenylacetic acids as the starting material, followed by the reaction of cyclization, coupling, deprotection, and finally introduced different substituted benzenesulfonamides. The structures of all target compounds were identified by ¹H NMR, ¹³C NMR and HRMS. The biological evaluation was performed on PC-3 (prostatic cancer cell), MDA-MB-231 (breast cancer cell) and K562 (chronic myelogenous leukemia cell) by 3-(4,5-dimethylthigal-2-yl)-2,5-(diphenyltetragalium) bromide (MTT) assay. The results suggested that some compounds exhibited good anti-proliferative activities against tumor cell lines. Especially, compounds 6a and 6b showed similar inhibitory activities against K562 cell compared with gossypol.
- thiadiazole,
- anticancer activity,
- synthesis
1. [1]
  [1] Jin, G. Y.; Hou, Z.; Zhao, G. F. Chem. Chin. Univ. 1997, 18, 409 (in Chinese). (金桂玉, 侯震, 赵国锋, 高等学校化学学报, 1997, 18, 409.)
2. [2]
  [2] Song, X. J.; Feng, G. R.; Chen, C. B.; Zhang, Z. W.; Wang, Y. G. Chin. J. Org. Chem. 2005, 25, 1587 (in Chinese). (宋新建, 冯桂荣, 陈传兵, 张政文, 汪炎钢, 有机化学, 2005, 25, 1587.)
3. [3]
  [3] (a) Badiger, N. P. Heterocycl. Commun. 2009, 15(6), 433. (b) Schirmer, U.; Plath, P.; Sauter, H.; Wuerzer, B. EP 84673, 1983 [Chem. Abstr. 1984, 100, 6519]. (c) Karki, S. S.; Panjamurthy, K.; Kumar, S.; Nambiar, M.; Ramareddy, S. A.; Chiruvella, K. K.; Raghavan, S. C. Eur. J. Med. Chem. 2011, 46, 2109. Karakus, S.; Rollas, S. Farmaco 2002, 57, 577.
4. [4]
  [4] Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Uysal, M. K.; Gfilen, D. Bioorg. Med. Chem. 2002, 10. 2893.
5. [5]
  [5] Schnone, S.; Brullo, C.; Bruno, O.; Bondavalli, F.; Ranise, A.; Filippeli, W.; Rinaldi, B.; Capuano, A.; Falcone, G. Bioorg. Med. Chem. 2006, 14, 1698.
6. [6]
  [6] Kumar, D.; Kumar, N. M.; Noel, B.; Kavita, S. Eur. J. Med. Chem. 2012, 55, 432.
7. [7]
  [7] Mougenot, P.; Namane, C. Fett, E.; Camy, F.; Dadji-Faïhun, R.; Langot, G.; Monseau, C.; Onofri, B.; Pacquet, F.; Pascal, C.; Crespin, O.; Ben-Hassine, M.; Ragot, J. L.; Van-Pham, T.; Philippo, C.; Chatelsin-Egger, F.; Péron, P.; Bail, J. C. L.; Guillot, E.; Chsmiot-Clerc, P.; Chabanaud, M. A.; Pruniaux, M. P.; Schmidt, F.; Venier, O.; Nicolaï, E.; Viviani, F. Bioorg. Med. Chem. Lett. 2012, 22, 2497.
8. [8]
  [8] Suzuki, K.; Hamada, Y.; Nguyen, J. T.; Kiso, Y. Bioorg. Med. Chem. 2013, 21, 6665.
9. [9]
  [9] Yang, X. H.; Xiang, L.; Li, X.; Zhao, T. T.; Zhang, H.; Zhou, W. P.; Wang, X. M.; Gong, H. B.; Zhu, H. L. Bioorg. Med. Chem. 2012, 20, 2789.
10. [10]
  [10] Guan, P.; Sun, F.; Hou, X.; Wang, F.; Yi, F.; Xu, W.; Fang, H. Bioorg. Med. Chem. 2012, 20(12), 3865.
11. [11]
  [11] Guan, P.; Wang, L.; Hou, X.; Wan, Y.; Xu, W.; Tang, W.; Fang, H. Bioorg. Med. Chem. 2014, 22(21), 5766.
12. [12]
  [12] SheppeckII, J. E.; Gilmore, J. L.; Xiao, H. Y.; Dhar, T. G. M.; Nirsch, D.; Doweyko, A. M.; Sack, J. S.; Corbett, M. J.; Malley, M. F.; Gougoutas, J. Z.; Mckay, L.; Cunningham, M. D.; Habte, S. F.; Dodd, J. H.; Nadler, S. G.; Somerville, J. E.; Barrish, J. C. Bioorg. Med. Chem. Lett. 2013, 23, 5442.
13. [13]
  [13] Rebolledo, C. L.; Sotelo-Hitschfeld, P.; Brauchi, S.; Olavarría, M. Z. Eur. J. Med. Chem. 2013, 66, 193.
14. [14]
  [14] Syed, S. A. S.; Rivera, G.; Ashfaq, M. Mini-Rev. Med. Chem. 2013, 13(1), 70.
15. [15]
  [15] Wang, J. H.; Wang, Q. D.; Dun, Y. Y.; Fang, H. Chem. Chin. Univ. 2014, 35, 1189 (in Chinese). (王军华, 王泉德, 顿艳艳, 方浩, 高等学校化学学报, 2014, 35, 1189.)
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沈阳化工大学材料科学与工程学院沈阳 110142