Synthesis and biological evaluation of novel 2-arylalkylthio-5-iodo-6-benzyl S-DABOs as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

doi:10.5246/jcps.2012.01.003

• 【Original articles】 • Previous Articles Next Articles

Synthesis and biological evaluation of novel 2-arylalkylthio-5-iodo-6-benzyl S-DABOs as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Liang Zhang, Xiao-Wei Wang, Jun-Yi Liu^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2011-06-03 Revised:2011-10-06 Online:2012-01-01 Published:2012-01-01
Contact: Jun-Yi Liu*

Abstract

CLC Number:

R916

Supporting:

Liang Zhang, Xiao-Wei Wang, Jun-Yi Liu^* . Synthesis and biological evaluation of novel 2-arylalkylthio-5-iodo-6-benzyl S-DABOs as potent non-nucleoside HIV-1 reverse transcriptase inhibitors [J]. , DOI: 10.5246/jcps.2012.01.003.

References

[1] Rodgers, D.W.; Gamblin, S.J.; Harris, B.A.; Ray, S.; Culp, J.S.; Hellmig, B.; Woolf, D.J.; Debouck, C.; Harrison, S.C. Proc. Natl. Acad. Sci. USA. 1995, 92, 1222-1226.
[2] Ting, Z.; Lan, X. Acta Pharm. Sin. 2004, 39, 666-672.
[3] Mugnaini, C.; Manetti, F.; Este, J.A.; Clotet-Codina, I.; Maga, G.; Cancio, R.; Botta, M.; Corelli, F. Bioorg. Med. Chem. Lett. 2006, 16, 3541-3544.
[4] Zhang, X. Acta Pharm. Sin. 2010, 45, 194-204.
[5] De Clercq, E. Chem. Biodivers. 2004, 1, 44-64.
[6] Wang, Y.; Chen, F.; De Clercq, E.; Balzarini, J.; Pannecouque, C. Eur. J. Med. Chem. 2009, 44, 1016-1023.
[7] Esnouf, R.M.; Stuart, D.I.; De Clercq, E.; Schwartz, E.; Balzarini, J. Biochem. Biophys. Res. Commn. 1997, 234, 458-464.
[8] Tantillo, C.; Ding, J.; Jacobo-Molina, A.; Nanni, R.G.; Boyer, P.L. J. Mol. Boil. 1994, 243, 369-387.
[9] Kohlstaedt, L.A.; Wang, J.; Friedman, J.M.; Rice, P.A.; Steits, T.A. Science. 1992, 256, 1783-1790.
[10] Das, K.; Lewi, P.J.; Hughes, S.H.; Arnold, E. Prog. Biophys. Mol. Biol. 2005, 88, 209-231.
[11] Meng, G.; Chen, F. Chin. J. Med. Chem. 2004, 14, 56-64.
[12] Morris, G.M.; Goodsell, D.S.; Halliday, R.S.; Huey, R.; Hart, W.E.; Belew, R.K.; Olson, A.J. J. Comput. Chem. 1998, 19, 1639-1662.
[13] Qin, H.; Liu, C.; Zhang, J.; Guo, Y.; Zhang, S.; Zhang, Z.; Wang, X.; Zhang, L.; Liu, J. Bioorg. Med. Chem. Lett. 2010, 20, 3003-3005.
[14] Aly, Y.L.; Pedersen, E.B.; La Colla, P.; Loddo, R. Arch. Pharm. Chem. Life Sci. 2007, 340, 225-235.
[15] Qin, H.; Liu, C.; Guo, Y.; Wang, R.; Zhang, J.; Ma, L.; Zhang, Z.; Wang, X.; Cui, Y.; Liu, J. Bioorg. Med. Chem. 2010, 18, 3231-3237.
[16] Davidson, D.; Berhardt, S.A. J. Am. Chem. Soc. 1948, 70, 3426-3428.
[17] Oikawa, Y.; Yoshioka, T.; Sugano, K.; Yonemitsu, O. Org. Synth. 1985, 63, 198-202.
[18] Mugnaini, C.; Alongi, M.; Togninelli, A.; Gevariya, H.; Rizzi, A.; Manetti, F.; Bernardini, C.; Angeli, L.; Tafi, A.; Bellucci, L.; Corelli, F.; Massa, S.; Maga, G.; Samuele, A.; Facchini, M.; Clotet-Codina, I.; Armand-Ugon, M.; Este, J.A.; Botta, M. J. Med. Chem. 2007, 50, 6580-6595.
[19] Manetti, F.; Esté, J.A.; Clotet-Codina, I.; Armand-Ugon, M.; Maga, G.; Crespan, E.; Cancio, R.; Mugnaini, C.; Bernardini, C.; Togninelli, A.; Carmi, C.; Alongi, M.; Petricci, E.; Massa, S.; Corelli, F.; Botta, M. J. Med. Chem. 2005, 48, 8000-8008.
[20] Asakura, J.; Robins, M.J. J. Org. Chem. 1990, 55, 4928-4933.
[21] Lu, X.; Chen, Y.; Guo, Y.; Liu, Z.; Shi, Y.; Xu, Y.; Wang, X.; Zhang, Z.; Liu, J. Bioorg. Med. Chem. 2007, 15, 7399-7407.

Synthesis and biological evaluation of novel 2-arylalkylthio-5-iodo-6-benzyl S-DABOs as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	Ningning Fan, Zhenming Liu, Xiaowei Wang, Junyi Liu. Docking and field-based QSAR studies of S-DABOs as HIV-1 reverse transcriptase inhibitors [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(7): 512-520.
[2]	Xiangyi Liu, Yuanyuan Cao, Yu Zhang, Quanzhi Yang, Xiaowei Wang, Junyi Liu. Route improvement of 3-substituted-4-(2-methylcyclohexyloxy)-6-phenethylpyridinone [J]. Journal of Chinese Pharmaceutical Sciences, 2014, 23(4): 220-224.
[3]	Han Yan, Xiao-Wei Wang^, Ying Guo, Zhi-Li Zhang, Jun-Yi Liu^ . Synthesis and anti-HIV-1 activity evaluation of N-1-alkyl-5-halogeno-6-alkylamino uracils as novel non-nucleoside HIV-1 reverse transcriptase inhibitors [J]. , 2011, 20(2): 146-153.
[4]	Wei Wang, Li Li, Chang Liu, Liang Zhang, Han Yan, Zhi-Li Zhang, Xiao-Wei Wang, Jun-Yi Liu^*. Synthesis and biological evaluation of novel 1-aryl-5-iodo-6-benzyluracils as potent HIV-1 non-nucleoside reverse transcriptase inhibitors [J]. , 2010, 19(4): 312-317.