Download PDF
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
› Author Affiliations
Further Information

Publication History

Received: 26 June 2014

Accepted after revision: 01 August 2014

Publication Date:
11 September 2014 (online)

    Permissions and Reprints All articles of this category


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
    Search in Google Scholar
  • 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
    CrossrefSearch in Google Scholar
  • 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
    CrossrefSearch in Google Scholar
  • 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
    CrossrefSearch in Google Scholar
    • 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
      CrossrefSearch in Google Scholar
    • 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
    CrossrefSearch in Google Scholar
  • 9 Jablonkai E, Milen M, Drahos L, Keglevich G. Tetrahedron Lett. 2013; 54: 5873
    CrossrefSearch in Google Scholar
  • 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
    Search in Google Scholar
  • 12 Sharnabai KM, Nagendra G, Vishwanatha TM, Sureshbabu VV. Tetrahedron Lett. 2013; 54: 478
    CrossrefSearch in Google Scholar
  • 13 Ramesha AB, Raghavendra GM, Nandeesh KN, Rangappa KS, Mantelingu K. Tetrahedron Lett. 2013; 54: 95
    CrossrefSearch in Google Scholar
  • 14 Sharath K, Kothanahally S, Swaroop TR, Harsha KB, Narasimhamurthy KH, Rangappa KS. Tetrahedron Lett. 2012; 53: 5619
    CrossrefSearch in Google Scholar
  • 15 Poojari S, Parameswar Naik P, Krishnamurthy G. Tetrahedron Lett. 2012; 53: 4639
    CrossrefSearch in Google Scholar
  • 16 Augustine JK, Bombrun A, Ramappa B, Boodappa C. Tetrahedron Lett. 2012; 53: 4422
    CrossrefSearch in Google Scholar
  • 17 Wen X, Bakali JE, Deprez-Poulain R, Deprez B. Tetrahedron Lett. 2012; 53: 2440
    CrossrefSearch in Google Scholar
  • 18 Desroses M, Wieckowski K, Stevens M, Odell LR. Tetrahedron Lett. 2011; 52: 4417
    CrossrefSearch in Google Scholar
    • 19a Jensen KA, Petersen C. Acta Chem. Scand. 1961; 15: 1087
      CrossrefSearch in Google Scholar
    • 19b For the preparation of other hydrazide starting materials, see ref. 6 and references cited therein.