Synthesis 2016; 48(21): 3701-3712
DOI: 10.1055/s-0035-1562435
paper
© Georg Thieme Verlag Stuttgart · New York

Easy Synthesis of Two Positional Isomeric Tetrazole Libraries

Yuanze Wang
,
Pravin Patil
,
Alexander Dömling*
Further Information

Publication History

Received: 04 April 2016

Accepted after revision: 03 May 2016

Publication Date:
21 June 2016 (online)


Abstract

A fast and efficient synthesis of libraries of positional isomeric 1H-tetrazoles and 5H-tetrazoles, for the purpose of testing binding hypothesis of isomeric tetrazoles in fragment-based drug discovery, is described.

Supporting Information

 
  • References

  • 1 These authors contributed equally to this article.
  • 2 Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. Nucleic Acids Res. 2000; 28: 235
    • 3a Herr RJ. Bioorg. Med. Chem. 2002; 23: 2699
    • 3b Matta CF, Arabi AA, Weaver DF. Eur. J. Med. Chem. 2010; 45: 1868
  • 4 Murray CW, Rees DC. Angew. Chem. Int. Ed. 2016; 55: 488
  • 5 Hoekstra WJ, Hargrove TY, Wawrzak Z, da Gama Jaen Batista D, da Silva Cristiane F, Nefertiti AS. G, Rachakonda G, Schotzinger RJ, Villalta F, Soeiro MC, Lepesheva GI. Antimicrob. Agents Chemother. 2016; 60: 1058
  • 6 Chen Y, Shoichet BK. Nat. Chem. Biol. 2009; 5: 158
    • 7a Wang K, Nguyen K, Huang Y, Dömling A. ACS. Comb. Sci. 2009; 11: 920
    • 7b Dömling A, Beck B, Fuchs T, Yazbak A. ACS Comb. Sci. 2006; 8: 872
  • 8 Finnegan WG, Henry RA, Lofquist R. J. Am. Chem. Soc. 1958; 80: 3908
    • 9a Mani P, Singh AK, Awasthi SK. Tetrahedron Lett. 2014; 55: 1879
    • 9b Gawande SD, Raihan MJ, Zanwar M, Kavala V, Janreddy D, Kuo CW, Chen ML, Kuo TS, Yao CF. Tetrahedron 2013; 69: 1841
    • 9c Gawande SD, Raihan MJ, Zanwar MR, Kavala V, Janreddy D, Kuo CW, Chen ML, Kuo TS, Yao CF. Tetrahedron 2013; 69: 1841
    • 9d Das B, Reddy CR, Kumar DN, Krishnaiah M, Narender R. Synlett 2010; 391
    • 9e Yoneyama H, Usami Y, Komeda S, Harusawa S. Synthesis 2013;  45: 1051
    • 9f Roh J, Artamonova TV, Vávrová K, Koldobskii GI, Hrabálek A. Synthesis 2009; 2175
    • 9g Vorona S, Artamonova T, Zevatskii Y, Myznikov L. Synthesis 2014;  46: 781
    • 9h Cantillo D, Gutmann B, Kappe CO.  J. Am. Chem. Soc. 2011;  133: 4465
  • 10 Kappe CO, Stadler A, Dallinger D. Microwaves in Organic and Medicinal Chemistry . In Methods and Principles in Medicinal Chemistry . Vol. 52. Mannhold R, Kubinyi H, Folkers G. Wiley-VCH; Weinheim: 2012: 487
  • 11 Oliveri-Mandala E, Alagna B. Gazz. Chim. Ital. 1910; 40 (II): 441