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Synthesis 2020; 52(10): 1523-1530
DOI: 10.1055/s-0037-1610754
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Glycosyl Carbamo(dithioperoxo)thioate Derivatives

Arin Gucchait
,
Sritin Ghosh
,
Anup Kumar Misra∗
Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India   Email: akmisra69@gmail.com
› Author AffiliationsA.G. thanks the Council of Scientific & Industrial Research (CSIR), New Delhi for providing a Senior Research Fellowship. This work was supported by the Science and Engineering Research Board (SERB), New Delhi (Project No. EMR/2015/000282).
Further Information

Publication History

Received: 31 December 2019

Accepted after revision: 03 February 2020

Publication Date:
25 February 2020 (online)

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Abstract

A straightforward, one-pot reaction procedure is developed for the synthesis of novel glycosylated carbamo(dithioperoxo)thioate derivatives via N-iodosuccinimide (NIS)-mediated condensation of different glycosyl thiols, carbon disulfide (CS2) and various amines. The reactions occur rapidly and afford good to high yields of the corresponding products.

Key words

carbohydrates - carbamo(dithioperoxo)thioates - one-pot - dithiocarbamates - glycomimetics

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610754.
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  • References

    • 1a Tamburrini A, Colombo C, Bernardi A. Med. Res. Rev. 2020; 40: 495
      CrossrefPubMed
    • 1b Sattin S, Bernardi A. Carbohydr. Chem. 2016; 41: 1
    • 1c Hevey R. Pharmaceuticals 2019; 12: 55
      CrossrefPubMed
    • 1d Magnani JL. Discovery Med. 2009; 8: 247
    • 2a Dosekova E, Filip J, Bertok T, Both P, Kasak P, Tkac J. Med. Res. Rev. 2017; 37: 514
      CrossrefPubMed
    • 2b Kirwan A, Utratna M, O’Dwyer ME, Joshi L, Kilcoyne M. Biomed. Res. Int. 2015; 2015: 490531
      PubMed
    • 2c Wang S.-K, Cheng C.-M. Chem. Commun. 2015; 51: 16750
      CrossrefPubMed
    • 3a Ernst B, Magnani JL. Nat. Rev. Drug Discovery 2009; 8: 661
      CrossrefPubMed
    • 3b Witczak ZJ, Boryczewski D. Bioorg. Med. Chem. Lett. 1998; 8: 3265
      CrossrefPubMed
    • 3c Pachamuthu K, Schmidt RR. Chem. Rev. 2006; 106: 160
      CrossrefPubMed
    • 3d Lázár L, Csávás M, Tóth M, Somsak L, Borbás A. Chem. Pap. 2015; 69: 889
    • 4a Scanlan EM, Corcé V, Malone A. Molecules 2014; 19: 19137
      CrossrefPubMed
    • 4b Galonic DP, Gin DY. Nature 2007; 446: 1000
      CrossrefPubMed
    • 4c Adamo R, Nilo A, Castagner B, Boutureira O, Berti F, Bernardes GJ. L. Chem. Sci. 2013; 4: 2995
      CrossrefPubMed
    • 4d von Itzstein M. Curr. Opin. Struct. Biol. 2008; 18: 558
      CrossrefPubMed
  • 5 Nieuwenhuizen PJ, Reedijk J, van Duin M, McGill WJ. Rubber Chem. Technol. 1997; 70, 368
    • 6a Wiessler M, Tacchi AM, Pool BL, Bertram B. J. Cancer Res. Clin. Biol. 1986; 111: 115
    • 6b Vaccari A, Ferraro L, Saba P, Ruiu S, Mocci I, Antonelli T, Tanganelli S. J. Pharmacol. Exp. Therap. 1998; 285: 961
  • 7 Eneanya DI, Bianchine JR, Duran DO, Andresen BD. Ann. Rev. Pharmacol. Toxicol. 1981; 21: 575
    CrossrefPubMed
  • 8 Cederbaum AI. Clin. Liver Dis. 2012; 16: 667
    CrossrefPubMed
  • 9 Sauna ZE, Shukla S, Ambudkar SV. Mol. Biosyst. 2005; 1: 127
    CrossrefPubMed
    • 10a Lin LZ, Lin J. Intl. J. Cancer 2011; 129: 1285
      CrossrefPubMed
    • 10b Kona RF, Buac D, Burger MA. Curr. Cancer Drug Targets 2011; 11: 338
      CrossrefPubMed
    • 10c Fisher CM. Arch. Neurol. 1989; 46: 798
      CrossrefPubMed
    • 10d Di Monte D, Irwin I, Kupsch A, Cooper S, De Lanney L, Langston JW. Eur. J. Pharmacol. 1989; 166: 23
      PubMed
  • 11 Cilibrasi V, Tsang K, Morelli M, Solfa F, Wiggins HL, Jones AT, Westwell AD. Tetrahedron Lett. 2015; 56: 2583
    Crossref
  • 12 Gucchait A, Joardar N, Parida PK, Roy P, Mukherjee N, Dutta A, Yesuvadian R, SinhaBabu SP, Jana K, Misra AK. Eur. J. Med. Chem. 2018; 143: 598
    CrossrefPubMed
  • 13 Liang F, Tan J, Piao C, Liu Q. Synthesis 2008; 3579
    Article in Thieme Connect
  • 14 Dutta S, Saha A. ChemistrySelect 2018; 3: 11895
    Crossref
  • 15 Jana M, Misra AK. J. Org. Chem. 2013; 78: 2680
    CrossrefPubMed
  • 16 Okamura T.-a, Kaga T, Yamashita S, Furuya R, Onitsuka K. J. Org. Chem. 2017; 82: 2187
    CrossrefPubMed
  • 17 Goto K, Yamamoto G, Tan B, Okazaki R. Tetrahedron Lett. 2001; 42: 4875
    Crossref
  • 18 Goto K, Holler M, Yamamoto G, Okazaki R. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 153: 313
    Crossref
  • 19 Minkwitz R, Lekies R. Z. Anorg. Allg. Chem. 1985; 527: 161
    Crossref
  • 20 Johnston BD, Pinto BM. J. Org. Chem. 2000; 65: 4607
    CrossrefPubMed
  • 21 Ge J.-T, Zhou L, Zhou F.-L, Dong H. J. Org. Chem. 2017; 82: 12613
    CrossrefPubMed