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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

SCImago Journal Rank (SJR) 2018: 0.263
Source Normalized Impact per Paper (SNIP) 2018: 0.505

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1865-7117
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Volume 72, Issue 10

Issues

Efficient synthesis of novel β-sitosterol scaffolds containing 1,2,3-triazole via copper(I)-catalyzed click reaction under microwave irradiation

Jin-Wei Yuan
  • Corresponding author
  • School of Chemistry and Chemical Engineering, Henan University of Technology; Academician Workstation for Natural Medical Chemistry of Henan Province, Zhengzhou 450001, P.R. China, Fax: +86 371 67756718
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  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ling-Bo Qu
  • School of Chemistry and Chemical Engineering, Henan University of Technology; Academician Workstation for Natural Medical Chemistry of Henan Province, Zhengzhou 450001, P.R. China
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2017-09-22 | DOI: https://doi.org/10.1515/znb-2017-0074

Abstract

In this work, new derivatives of the β-sitosterol scaffolds containing 1,2,3-triazole are prepared by the reaction of β-sitosterol with aromatic alkynes via copper(I)-catalyzed azide-alkyne cycloaddition reactions under microwave irradiation. The reaction has several advantages including high yields, short reaction times, and a simple work-up procedure.

This article offers supplementary material which is provided at the end of the article.

Keywords: click reaction; Cu(I)-catalyzed; β-sitosterol; steroid; 1,2,3-triazole

References

  • [1]

    E. Sosińska, R. Praybylski, P. Hazendonk, Y. Y. Zhao, J. M. Curtis, Food Chem. 2013, 139, 464.CrossrefGoogle Scholar

  • [2]

    R. A. Moreau, B. D. Whitaker, K. B. Hicks, Prog. Lipid Res. 2002, 41, 457.CrossrefGoogle Scholar

  • [3]

    A. Malaviya, J. Gomes, Bioresour. Technol. 2008, 99, 6725.CrossrefGoogle Scholar

  • [4]

    G. Gu, Y. Du, R. J. Linhardt, J. Org. Chem. 2004, 69, 5497.CrossrefGoogle Scholar

  • [5]

    C. D. Hufford, S. Liu, A. M. Clark, J. Nat. Prod. 1988, 51, 94.CrossrefGoogle Scholar

  • [6]

    J. Zhou, Pure Appl. Chem. 1989, 61, 457.Google Scholar

  • [7]

    A. M. Deobald, L. R. S. Camargo, D. Alves, J. Zukerman-Schpector, A. G. Corrêa, M. W. Paixão, Synthesis 2011, 2011, 4003.CrossrefGoogle Scholar

  • [8]

    B. M. Folmer, Adv. Colloid Interf. Sci. 2003, 103, 99.CrossrefGoogle Scholar

  • [9]

    M. Pang, S. T. Jiang, L. L. Cao, L. J. Pan, J. Agric. Food Chem. 2011, 59, 10732.CrossrefGoogle Scholar

  • [10]

    P. J. H. Jones, D. E. MacDougall, F. Ntanios, C. A. Vanstone, Can. J. Physiol. Pharmacol. 1997, 75, 217.CrossrefGoogle Scholar

  • [11]

    D. W. Chung, Y. T. Choi, J. Ind. Eng. Chem. 2007, 13, 367.Google Scholar

  • [12]

    A. Berger, P. J. H. Jones, S. S. Abumweis, Lipids Health Dis. 2004, 3, 5.CrossrefGoogle Scholar

  • [13]

    F. O. MaCarthy, J. Chopra, A. Ford, S. A. Hogan, J. P. Kerry, N. M. O’Brien, E. Ryan, A. R. Maguire, Org. Biomol. Chem. 2005, 3, 3059.CrossrefGoogle Scholar

  • [14]

    A. B. Awad, Y. C. Chen, C. S. Fink, T. Hennessey, Anticancer Res. 1996, 16, 2797.Google Scholar

  • [15]

    R. L. von Holtz, C. S. Fink, A. B. Awad, Nutr. Cancer 1998, 32, 8.CrossrefGoogle Scholar

  • [16]

    A. B. Awad, A. C. Downie, C. S. Fink, Int. J. Mol. Med. 2000, 5, 541.Google Scholar

  • [17]

    A. B. Awad, M. D. Garcia, C. S. Fink, Nutr. Cancer 1997, 29, 212.CrossrefGoogle Scholar

  • [18]

    D. O. Moon, M. O. Kim, Y. H. Choi, G. Y. Kim, Cancer Lett. 2008, 264, 181.CrossrefGoogle Scholar

  • [19]

    Y. Pouilloux, G. Courtois, M. Boisseau, A. Piccirilli, J. Barrault, Green Chem. 2003, 5, 89.CrossrefGoogle Scholar

  • [20]

    M. Mikolajczyk, P. Keillasinki, Tetrahedron 1981, 37, 233.Google Scholar

  • [21]

    N. N. Farshori, M. R. Banday, Z. Zahoor, A. Rauf, Chin. Chem. Lett. 2010, 21, 646.CrossrefGoogle Scholar

  • [22]

    W. Panpipat, X. B. Xu, Z. Guo, Biochem. Eng. J. 2013, 70, 55.CrossrefGoogle Scholar

  • [23]

    J. G. Cui, H. Wang, Y. M. Huang, Y. Xin, A. M. Zhou, Steroids 2009, 74, 1057.CrossrefGoogle Scholar

  • [24]

    X. Zhang, P. Geoffroy, M. Miesch, D. Julien-David, F. Raul, D. Aoudé-Werner, E. Marchioni, Steroids 2005, 70, 886.CrossrefGoogle Scholar

  • [25]

    P. W. Baures, Org. Lett. 1999, 1, 249.CrossrefGoogle Scholar

  • [26]

    L. H. Lu, J. H. Wu, C. H. Yang, J. Chin. Chem. Soc. 2008, 55, 414.CrossrefGoogle Scholar

  • [27]

    S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 2011, 6, 2696.CrossrefGoogle Scholar

  • [28]

    A. Lauria, R. Delisi, F. Mingoia, A. Terenzi, A. Martorana, G. Barone, A. M. Almerico, Eur. J. Org. Chem. 2014, 2014, 3289.CrossrefGoogle Scholar

  • [29]

    D. R. Buckle, D. J. Outred, C. J. M. Rockell, H. Smith, B. A. Spicer, J. Med. Chem. 1983, 26, 251.CrossrefGoogle Scholar

  • [30]

    D. R. Buckle, C. J. Rockell, H. Smith, B. A. Spicer, J. Med. Chem. 1986, 29, 2262.CrossrefGoogle Scholar

  • [31]

    R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, C. F. Perno, A. Karlsson, J. Balzarini, M. J. Camarasa, J. Med. Chem. 1994, 37, 4185.CrossrefGoogle Scholar

  • [32]

    P. Appukkuttan, W. Dehaen, V. V. Fokin, E. V. D. Eycken, Org. Lett. 2004, 6, 4223.CrossrefGoogle Scholar

  • [33]

    V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596.CrossrefGoogle Scholar

  • [34]

    A. E. Speers, G. C. Adam, B. F. Cravatt, J. Am. Chem. Soc. 2003, 125, 4686.CrossrefGoogle Scholar

  • [35]

    W. H. Binder, C. Kluger, Curr. Org. Chem. 2006, 10, 1791.CrossrefGoogle Scholar

  • [36]

    M. Whiting, J. Muldoon, Y. C. Lin, S. M. Silverman, W. Lindstrom, A. J. Olson, H. C. Kolb, M. G. Finn, K. B. Sharpless, J. H. Elder, V. V. Fokin, Angew. Chem. Int. Ed. 2006, 45, 1435.CrossrefGoogle Scholar

  • [37]

    D. B. Ramachary, A. B. Shashank, S. Karthik, Angew. Chem. Int. Ed. 2014, 53, 10420.CrossrefGoogle Scholar

  • [38]

    V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 114, 2708.CrossrefGoogle Scholar

  • [39]

    J. E. Hein, V. V. Folin, Chem. Soc. Rev. 2010, 39, 1302.CrossrefGoogle Scholar

  • [40]

    M. S. Singh, S. Chowdhury, S. Koley, Tetrahedron 2016, 72, 5257.CrossrefGoogle Scholar

  • [41]

    V. K. Tiwari, B. B. Mishra, K. B. Mishra, N. Mishra, A. S. Singh, X. Chen, Chem. Rev. 2016, 116, 3086.CrossrefGoogle Scholar

  • [42]

    G. Fran, A. K. Kakkar, Chem. Soc. Rev. 2010, 39, 1536.CrossrefGoogle Scholar

  • [43]

    P. M. E. Gramlich, C. T. Wirges, A. Manetto, T. Carell, Angew. Chem. Int. Ed. 2008, 47, 8350.CrossrefGoogle Scholar

  • [44]

    W. W. Zhao, H. Li, J. Zhang, S. Cao, Chin. J. Chem. 2011, 29, 2763.CrossrefGoogle Scholar

  • [45]

    X. L. Chen, X. Li, J. W. Yuan, L. B. Qu, S. H. Wang, H. Y. Shi, Y. C. Tang, L. K. Duan, Tetrahedron 2013, 69, 4047.CrossrefGoogle Scholar

  • [46]

    J. Luo, H. Par, Bull Korean Chem. Soc. 2014, 35, 3645.CrossrefGoogle Scholar

  • [47]

    J. W. Yuan, L. R. Yang, Y. M. Xiao, L. B. Qu, Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1358.CrossrefGoogle Scholar

  • [48]

    J. W. Yuan, Q. Y. Yin, Y. Z. Li, P. Mao, L. R. Yang, Y. M. Xiao, L. B. Qu, Chin. J. Magn. Reson. 2016, 33, 327.Google Scholar

  • [49]

    Y. Z. Li, L. Qiu, Q. Y. Yin, P. Mao, Y. M. Xiao, L. B. Qu, J. W. Yuan, Chin. J. Magn. Reson. 2016, 33, 133.Google Scholar

  • [50]

    J. Rull-Barrull, M. d’Halluin, E. L. Grognec, F. X. Felpin, Angew. Chem. Int. Ed. 2016, 55, 13549.CrossrefGoogle Scholar

About the article

Received: 2017-05-11

Accepted: 2017-07-05

Published Online: 2017-09-22

Published in Print: 2017-09-26


Citation Information: Zeitschrift für Naturforschung B, Volume 72, Issue 10, Pages 717–724, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2017-0074.

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