Citation: Chen Hua, Shao Jie, Zhu Mo, Li Xiaoliu. Design, Synthesis and Anti-HIV-Reverse Transcriptase Activity of Novel Diaryl Thiazolindin-4-one Derivatives Possessing Amide Linkage on N-3 Position[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 527-532. doi: 10.6023/cjoc201509043 shu

Design, Synthesis and Anti-HIV-Reverse Transcriptase Activity of Novel Diaryl Thiazolindin-4-one Derivatives Possessing Amide Linkage on N-3 Position

1.
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Chen Hua, Li Xiaoliu,
Received Date: 30 September 2015
Available Online: 2 December 2015
Fund Project: 国家自然科学基金(No. 21372060) (No. 21372060)河北省自然科学杰出青年基金(培育)(No. B2015201005). (培育)(No. B2015201005)

A series of thiazolidin-4-one derivatives possessing ester were synthesized under microwave irradiation using amino acid ester as starting material. After ester hydrolysis reaction and amide condensation reaction, the aimed diaryl thiazolindin-4-one derivatives possessing amide linkage on N-3 position were obtained. The compounds were evaluated for their human immunodeficiency virus (HIV-1) reverse transcriptase (RT) inhibitory activities in vitro HIV-1 RT kit assay (colorimetric method). The results showed that some of the compounds, such as 5bb, 5bc, 5cb, and 5cc could effectively inhibit RT activity with the IC₅₀ values of 4.15, 3.53, 4.61 and 4.06 μmol/L, respectively. Structure activity relationship analysis of these analogues suggested that the introduction of two carbons side chain on N-3 position and lipophilic group like methyl group should be favorable to their anti-HIV-RT activitives.
- thiazolidin-4-one,
- anti-HIV-RT activity,
- lipophilic group,
- flexible side chain,
- amide bond
1. [1]
  [1] Verma, A.; Saraf, S. K. Eur. J. Med. Chem. 2008, 43, 897.
2. [2]
  [2] Tripathi, A. C.; Gupta, S. J.; Fatima, G. N.; Sonar, P. K.; Verma, A.; Saraf, S. K. Eur. J. Med. Chem. 2014, 72, 52.
3. [3]
  [3] Reynold, C.; de Koning, C. B.; Pelly, S. C.; van Otterlo, W. A. L.; Bode. M. L. Chem. Soc. Rev. 2012, 41, 4657.
4. [4]
  [4] Tian Y.; Zhan P.; Rai, D.; Zhang, J. Y.; De Clercq, E.; Liu, X. Y. Curr. Med. Chem. 2012, 19, 2026.
5. [5]
  [5] Hao, G. F.; Yang, G. F. Chin. J. Org. Chem. 2008, 28, 1545 (in Chinese). (郝格非, 杨光富, 有机化学, 2008, 28, 1545.)
6. [6]
  [6] Zhan, P.; Chen, X. W.; Li, D. Y.; Fang, Z. J.; De Clercq, E.; Liu, X. Y. Med. Res. Rev. 2013, 33(suppl. 1), E1.
7. [7]
  [7] Rawal, R. K.; Tripathi, R.; Katti, S. B.; Pannecouque, C.; De Clercq, E. Eur. J. Med. Chem. 2008, 43, 2800.
8. [8]
  [8] Rawal, R. K.; Tripathi, R.; Katti, S. B.; Pannecouque, C.; De Clercq, E. Bioorg. Med. Chem. 2007, 15, 3134.
9. [9]
  [9] Rawal, R. K.; Tripathi, R.; Kulkarni, S.; Paranjape, R.; Katti, S. B.; Pannecouque, C.; De Clercq, E. Chem. Biol. Drug Des. 2008, 72, 147.
10. [10]
  [10] Chen, H.; Bai, J.; Jiao, L. L.; Guo, Z. H.; Yin, Q. M., Li, X. L. Bioorg. Med. Chem. 2009, 17, 3980.
11. [11]
  [11] Ravichandran, V.; Prashantha, K. B. R.; Sankar, S.; Agrawal, R. K. Eur. J. Med. Chem. 2009, 44, 1180.
12. [12]
  [12] Singh, A.; Yadav, D.; Yadav, M.; Dhamanage, A.; Kulkarni, S.; Singh, R. K. Chem. Biol. Drug Des. 2015, 85, 336.
13. [13]
  [13] DiMauro, E. F.; Newcomb, J.; Nunes, J. J.; Bemis, J. E.; Boucher, C.; Chai, L.; Chaffee, S. C.; Deak, H. L.; Epstein, L. F.; Faust, T.; Gallant, P.; Gore, A.; Gu, Y.; Henkle, B.; Hsieh, F.; Huang, X.; Kim J. L.; Lee, J. H.; Martin, M. W.; McGowan, D. C.; Metz, D.; Mohn, D.; Morgenstern, K. A.; Oliveira-dos-Santos, A.; Patel, V. F.; Powers, D.; Rose, P. E.; Schneider, S.; Tomlinson, S. A.; Tudor, Y. Y.; Turci, S. M.; Welcher, A. A.; Zhao, H.; Zhu, L.; Zhu, X. J. Med. Chem. 2008, 51, 1681.
14. [14]
  [14] Chen, H.; Yuan, X. G.; Guo, Z. H.; Zhao, L.; Li, X. L.; Zhang. J. C. J. Hebei Univ. (Nat. Sci. Ed.) 2009, 29, 153 (in Chinese). (陈华, 苑香果, 郭在红, 赵莲, 李小六, 张金超, 河北大学学报自然科学版, 2009, 29, 153.)
15. [15]
  [15] Zhou, Z. Z.; Huang, W.; Ji, F. Q.; Ding, M. W.; Yang, G. F. Heteroat. Chem. 2007, 18, 381.
16. [16]
  [16] Gududuru, V.; Nguyen, V.; Dalton, J. T.; Miller, D. D. Synlett 2004, 2357.
17. [17]
  [17] Holmes, C. P.; Chinn, J. P.; Look, G. C.; Gordon, E. M.; Gallop, M. A. J. Org. Chem. 1995, 60, 7328.
18. [18]
  [18] Chen, H.; Huang, C. J.; Zhu, M.; Li, X. L. Chin. J. Org. Chem. 2014, 34, 756 (in Chinese). (陈华, 黄长军, 朱墨, 李小六, 有机化学, 2014, 34, 756.)
19. [19]
  [19] Reverse Transcriptase Assay, Colorimetric kit, Roche Diagnostics GmbH, Roche Applied Science, Sandhofer Strasse 116, D-68305 Mannheim, Germany.
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