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Synthesis and antitumor activity of 1-deoxybaccatin III analogs from 1-deoxybaccatin VI

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Abstract

Several new 1-deoxybaccatin III analogs were conveniently synthesized from 1-deoxybaccatin VI with the aim of having modified ester groups at C-2 and C-4. The antitumor activity of these compounds was evaluated. The preliminary SAR analysis showed that the electronic properties of the terminal group in the substituent on C4, C9, and C10 constituted important factors to the cytotoxic activities against A 549 and MCF-7 cell lines. The present studies provide a new synthetic basis for development of new 1-deoxypaclitaxel analogs.

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References

  1. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) J Am Chem Soc 93:2325

    Article  CAS  Google Scholar 

  2. Kingston DGI (2001) Chem Commun 10:867

    Article  Google Scholar 

  3. Kingston DGI, Chordia MD, Jagtap PG, Liang JY, Shen YC, Long BH, Fairchild CR, Johnston KA (1999) J Org Chem 64:1814

    Article  CAS  Google Scholar 

  4. Chaudhary AG, Chordia MD, Kingston DGI (1995) J Org Chem 60:3260

    Article  CAS  Google Scholar 

  5. Chen SH, Huang S, Gao Q, Golik J, Farina V (1994) J Org Chem 59:1475

    Article  CAS  Google Scholar 

  6. Yin DL, Sekiguchi Y, Kameo K (1998) Chin Chem Lett 9:373

    CAS  Google Scholar 

  7. Horiguchi T, Oritani T, Kiyota H (2003) Tetrahedron 59:1529

    Article  CAS  Google Scholar 

  8. Zhang M, Yin D, Guo JY, Liang XT (2005) Tetrahedron 61:5519

    Article  CAS  Google Scholar 

  9. Lin HX, Li M, Chen JM, Chen MQ (2004) Chin J Chem 22:751

    Article  CAS  Google Scholar 

  10. Lin HX, Han N, Chen JM, Yuan TH (2006) J Chem Crystallogr 36:337

    Article  CAS  Google Scholar 

  11. Zefirova ON, Nurieva EV, Ryzhov AN, Zyk NV, Zefirov NS (2005) Russ J Org Chem 41:315

    Article  CAS  Google Scholar 

  12. GueÂnard D, Thoret S, Dubois J, Adeline MT, Wang Q, Guéritte F (2000) Bioorg Med Chem 8:145

    Article  Google Scholar 

  13. Spletstoser JT, Turunen BJ, Desino K, Rice A, Datta A, Dutta D, Huff JK, Himes RH, Audus KL, Seelig A, Georg GI (2006) Bioorg Med Chem Lett 16:495

    Article  CAS  Google Scholar 

  14. Chordia MD, Yuan H, Jagtap PG, Kadow JF, Long BH, Fairchild CR, Johnston KA, Kingston DGI (2001) Bioorg Med Chem 9:171

    Article  CAS  Google Scholar 

  15. Chen SH, Farina V, Vyas DM, Doyle TW (1998) Bioorg Med Chem Lett 8:2227

    Article  CAS  Google Scholar 

  16. He L, Jagtap PG, Kingston DGI, Shen HJ, Orr GA, Horwitz SB (2000) Biochemistry 39:3972

    Article  CAS  Google Scholar 

  17. Hasegawa T, Ba J, Zhang S, Wang J, Matsubara J, Kawakami J, Tomida A, Tsuruo T, Hirose K, Sakai J, Kikuchi M, Abe M, Ando M (2007) Bioorg Med Chem Lett 17:1122

    Article  CAS  Google Scholar 

  18. Yuan TH, Jiang Y, Wang XH, Wang DL, Bannerjee A, Bane S, Snyder JP, Lin HX (2008) Bioorg Med Chem Lett 19:1148

    Article  CAS  Google Scholar 

  19. Jin DH, Cui YM, Lin HX (2012) Med Chem 8:789

    Article  CAS  Google Scholar 

  20. Lin HX, Jiang Y, Chen JM, Chen JK, Chen MQ (2005) J Mol Struct 738:59

    Article  CAS  Google Scholar 

  21. Chen SH, Wei JM, Long BH, Fairchild CR, Carboni J, Mamber SW, Rose WC, Johnston K, Casazza AM, Kadow JF, Farina V, Vyas DM, Doyle TW (1995) Bioorg Med Chem Lett 5:2741

    Article  CAS  Google Scholar 

  22. Ishiyama T, Iimura S, Ohsuki S, Uoto K, Terasawa H, Soga T (2002) Bioorg Med Chem Lett 12:1083

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful for support from the National Natural Science Foundation of China (Project No. 21272154, 81202402, and 30672506), Leading Academic Discipline Project of Shanghai Municipal Education Commission (Project No. J50102), and Shanghai Pujiang Program (No. 10PJ1403700). The authors also thank Dr. H. Deng and The Instrumental Analysis & Research Center of Shanghai University for structural analysis.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shanghai University, Shanghai, 200444, People’s Republic of China

    Yuan-You Qiu, Hai-Xia Lin, Yong-Mei Cui, Jun-Chao Shao & Dan-Hui Jin

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  1. Yuan-You Qiu
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  2. Hai-Xia Lin
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  3. Yong-Mei Cui
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  4. Jun-Chao Shao
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  5. Dan-Hui Jin
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Correspondence to Hai-Xia Lin or Yong-Mei Cui.

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Qiu, YY., Lin, HX., Cui, YM. et al. Synthesis and antitumor activity of 1-deoxybaccatin III analogs from 1-deoxybaccatin VI. Monatsh Chem 144, 1573–1582 (2013). https://doi.org/10.1007/s00706-013-0981-z

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  • DOI: https://doi.org/10.1007/s00706-013-0981-z

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