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Synthesis 2014; 46(24): 3394-3398
DOI: 10.1055/s-0034-1378664
paper
© Georg Thieme Verlag Stuttgart · New York

Facile and Convenient Synthesis of N′1,N′3-Dialkyl-N′1,N′3-bis(arylcarbonothioyl)malonohydrazides via Propylphosphonic Anhydride Coupling

Zhiqiang Xia
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Jun Jiang
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Lijun Sun
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Noriaki Tatsuta
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Keizo Koya
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Junyi Zhang
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Gary Bohnert
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
,
Shoujun Chen*
Synta Pharmaceuticals Corp., 45 Hartwell Ave., Lexington, MA 02421, USA   Fax: +1(781)2748228   eMail: schen@syntapharma.com
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Publikationsverlauf

Received: 26. Juni 2014

Accepted after revision: 01. August 2014

Publikationsdatum:
11. September 2014 (online)

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Dedicated to Professor Chengye Yuan and Professor Li-Xin Dai of the Shanghai Institute of Organic Chemistry (CAS) on the occasion of their 90th birthdays

Abstract

A facile and convenient synthetic method for the anticancer agent elesclomol and its analogues, N′1,N′3-dialkyl-N′1,N′3-bis(arylcarbonothioyl)malonohydrazides, by the direct coupling of N-alkyl-N-(substituted)benzothiohydrazides and substituted malonic acids using propylphosphonic anhydride (T3P®) under very mild conditions has been developed.

Key words

propylphosphonic anhydride - elesclomol - analogues - synthesis - anticancer agents
 

  • References

  • 1 Sun L, Chen S, Koya K, Xia Z.-Q, Tatsuta N, Korbut T, Du Z, Liang G, Zhou D, Ono M. Abstracts of Papers, 227th ACS National Meeting, Anaheim, CA, March 28–April 1, 2004. American Chemical Society; Washington DC: 2004. Abstract MEDI 111
    Google Scholar
    • 2a Hasinoff BB, Yalowich JC, Patel D, Yadav A, Wu X. Cancer Res. 2013; 73 (08) Abstract 5559 ; DOI: 10.1158/1538-7445.AM2013-5559
    • 2b Wangpaichitr M, Wu C, You M, Maher JC, Dinh V, Feun LG, Savaraj N. Cancers 2009; 1: 23
      Crossref
    • 2c Qu Y, Wang J, Sim M.-S, Liu B, Giuliano A, Barsoum J, Cui X. Breast Cancer Res. Treat. 2010; 121: 311
      Crossref
    • 2d Revill P, Mealy N, Serradell N, Rosa E, Bolos J. Drugs Future 2008; 33: 310
      Crossref
    • 2e Bair JS, Palchaudhuri R, Hergenrother PJ. J. Am. Chem. Soc. 2010; 132: 5469
      Crossref
  • 3 Berkenblit A, Eder JP. Jr, Ryan DP, Seiden MV, Tatsuta N, Sherman ML, Dahl TA, Dezube BJ, Supko JG. Clin. Cancer Res. 2007; 13: 584
    Crossref
  • 4 O’Day S, Gonzalez R, Lawson D, Weber R, Hutchins L, Anderson C, Haddad J, Kong S, Williams A, Jacobson E. J. Clin. Oncol. 2009; 27: 5452
    Crossref
  • 5 O’Day SJ, Eggermont AM, Chiarion-Sileni V, Kefford R, Grob JJ, Mortier L, Robert C, Schachter J, Testori A, Mackiewicz J, Friedlander P, Garbe C, Ugurel S, Collichio F, Guo W, Lufkin J, Bahcall S, Vukovic V, Hauschild A. J. Clin. Oncol. 2013; 31: 1211
    Crossref
    • 6a Chen S, Sun L, Koya K, Tatsuta N, Xia Z, Kobut T, Du Z, Wu J, Liang G, Jiang J, Ono M, Zhou D, Sonderfan A. Bioorg. Med. Chem. Lett. 2013; 23: 5070
      Crossref
    • 6b Chen S, Sun L, Xia Z, Koya K, Ono M. US Patent 6825235, 2004
    • 6c Chen S, Sun L, Xia Z, Koya K, Ono M. WO 2003006429, 2003
  • 7 Vo NH, Xia Z, Hanko J, Yun T, Bloom S, Shen J, Koya K, Sun L, Chen S. J. Inorg. Biochem. 2014; 130: 69
    Crossref

      • For general reviews and references on T3P®, see:
    • 8a Wissmann H, Kleiner H.-J. Angew. Chem. 1980; 92: 133
      Crossref
    • 8b Meudt A, Wisdom R. Chim. Oggi 2008; 26: 28
    • 8c Basavaprabhu Vishwanatha TM, Panguluri NR, Sureshbabu VV. Synthesis 2013; 45: 1569
      Artikel in Thieme Connect
    • 8d Magano J, Bock B, Brennan J, Farrand D, Lovdahl M, Maloney MT, Nadkarni D, Oliver WK, Pozzo MJ, Teixeira JJ, Wang J, Rizzo J, Tumelty D. Org. Process Res. Dev. 2014; 18: 142
      Crossref
  • 9 Jablonkai E, Milen M, Drahos L, Keglevich G. Tetrahedron Lett. 2013; 54: 5873
    Crossref
  • 10 Desroses M, Jacques-Cordonnier M.-C, Llona-Minguez S, Jacques S, Koolmeister T, Helleday T, Scobie M. Eur. J. Org. Chem. 2013; 5879
  • 11 Desroses M, Koolmeister T, Jacques S, Llona-Minguez S, Jacques-Cordonnier M.-C, Cazares-Korner A, Helleday T, Scobie M. Tetrahedron Lett. 2013; 54: 3554
  • 12 Sharnabai KM, Nagendra G, Vishwanatha TM, Sureshbabu VV. Tetrahedron Lett. 2013; 54: 478
    Crossref
  • 13 Ramesha AB, Raghavendra GM, Nandeesh KN, Rangappa KS, Mantelingu K. Tetrahedron Lett. 2013; 54: 95
    Crossref
  • 14 Sharath K, Kothanahally S, Swaroop TR, Harsha KB, Narasimhamurthy KH, Rangappa KS. Tetrahedron Lett. 2012; 53: 5619
    Crossref
  • 15 Poojari S, Parameswar Naik P, Krishnamurthy G. Tetrahedron Lett. 2012; 53: 4639
    Crossref
  • 16 Augustine JK, Bombrun A, Ramappa B, Boodappa C. Tetrahedron Lett. 2012; 53: 4422
    Crossref
  • 17 Wen X, Bakali JE, Deprez-Poulain R, Deprez B. Tetrahedron Lett. 2012; 53: 2440
    Crossref
  • 18 Desroses M, Wieckowski K, Stevens M, Odell LR. Tetrahedron Lett. 2011; 52: 4417
    Crossref
    • 19a Jensen KA, Petersen C. Acta Chem. Scand. 1961; 15: 1087
      Crossref
    • 19b For the preparation of other hydrazide starting materials, see ref. 6 and references cited therein.