Synthesis 2014; 46(18): 2451-2462
DOI: 10.1055/s-0033-1339139
paper
© Georg Thieme Verlag Stuttgart · New York

Oxazole/Thiazole and Triazole Hybrids Based on α-Amino Acids

Guillermo Valdomir
a   Cátedra de Química Farmacéutica, DQO, Facultad de Química, UdelaR, Av General Flores 2124, 11800 Montevideo, Uruguay   Fax: +598(2)9241906   eMail: ddavyt@fq.edu.uy
,
Juan I. Padrón
b   Instituto de Productos Naturales y Agrobiología, CSIC, C/ Astrofísico Francisco Sánchez 3, 38206 La Laguna, Spain
c   Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
José M. Padrón
c   Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
Víctor S. Martín
c   Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Sánchez 2, 38206 La Laguna, Spain
,
Danilo Davyt*
a   Cátedra de Química Farmacéutica, DQO, Facultad de Química, UdelaR, Av General Flores 2124, 11800 Montevideo, Uruguay   Fax: +598(2)9241906   eMail: ddavyt@fq.edu.uy
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Weitere Informationen

Publikationsverlauf

Received: 30. Januar 2014

Accepted after revision: 29. April 2014

Publikationsdatum:
04. Juni 2014 (online)


Abstract

The Cu(I)-catalyzed Huisgen [3+2] cycloaddition is the basis of click chemistry to synthesize triazole derivatives by coupling azides with ethynyl blocks. In the development of new compounds inspired by bioactive natural products, the synthesis of new oxazole building blocks containing azide moiety and coupling them with aromatic alkynes via triazole linker is described. These oxazole building blocks are synthesized using amino acids as chiral and inexpensive starting materials. Using this approach, 16 new triazole-oxazole hybrids were synthesized.

Supporting Information

 
  • References

    • 1a Miranda PO, Díaz DD, Padrón JI, Bermejo J, Martín VS. Org. Lett. 2003; 11: 1979
    • 1b Carballo RM, Ramírez MA, Rodríguez ML, Martín VS, Padrón JI. Org. Lett. 2006; 8: 3837
    • 1c Miranda PO, Padrón JM, Padrón JI, Villar J, Martín VS. ChemMedChem 2006; 1: 323
    • 1d Purino MA, Ramírez MA, Daranas AH, Martín VS, Padrón JI. Org. Lett. 2012; 14: 5904
    • 1e Rutkowski J, Brzezinski B. Biomed. Res. Int. 2013; 2013: 162513
    • 2a García C, Soler MA, Martín VS. Tetrahedron Lett. 2000; 41: 4127
    • 2b Crisóstomo FR. P, Carrillo R, León LG, Martín T, Padrón JM, Martín VS. J. Org. Chem. 2006; 71: 2339
    • 2c Díaz DD, Betancort JM, Martín VS. Synlett 2007; 343
    • 2d Rodríguez-López J, Crisóstomo FP, Ortega N, López-Rodríguez M, Martín VS, Martín T. Angew. Chem. Int. Ed. 2013; 52: 3659
    • 2e Martín T, Martín VS, Padrón JI. Synlett 2014; 25: 12
  • 3 McNally A, Prier CK, MacMillan DW. Science 2011; 334: 1114
    • 4a Jin Z. Nat. Prod. Rep. 2013; 30: 869
    • 4b Davyt D, Serra G. Mar. Drugs 2010; 8: 2755
    • 4c Yeh VS. C. Tetrahedron 2004; 60: 11995
    • 5a Gant TG, Meyers AI. Tetrahedron 1994; 50: 2927
    • 5b Meyers AI, Tavares F. Tetrahedron Lett. 1994; 35: 2481
  • 6 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
  • 7 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
  • 8 Yoon J, Ryu JS. Bioorg. Med. Chem. Lett. 2010; 20: 3930
    • 9a Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
    • 9b Chrysina ED, Bokor É, Alexacou K-M, Charavgi M-D, Oikonomakos GN, Zographos SE, Leonidas DD, Oikonomakos NG, Somsák L. Tetrahedron: Asymmetry 2009; 20: 733
    • 9c Colombo F, Tintori C, Furlan A, Borrelli S, Christodoulou MS, Dono R, Maina F, Botta M, Amat M, Bosch J, Passarella D. Bioorg. Med. Chem. Lett. 2012; 22: 4693
    • 10a Metha G, Singh V. Chem. Soc. Rev. 2002; 31: 324
    • 10b Tietze LF, Bell HP, Chandrasekhar S. Angew. Chem. Int. Ed. 2003; 42: 3996
    • 11a Mann E, Chana A, Sánchez-Sancho F, Puerta C, García-Merino A, Herradón B. Adv. Synth. Catal. 2002; 344: 855
    • 11b Steiner AJ, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM. Carbohydr. Res. 2007; 342: 1850
    • 11c Banerjee A, Sergienko E, Vasile S, Gupta V, Vuori K, Wipf P. Org. Lett. 2009; 11: 65
    • 11d Burov S, Leko M, Dorosh M, Dobrodumov A, Veselkina O. J. Pept. Sci. 2011; 17: 620
  • 12 Hou J, Li Z, Fang Q, Feng C, Zhang H, Guo W, Wang H, Gu G, Tian Y, Liu P, Liu R, Lin J, Shi Y, Yin Z, Shen J, Wang PG. J. Med. Chem. 2012; 55: 3066
  • 13 Li W, Chou H. Synthesis 2000; 84
  • 14 Phillips AJ, Uto Y, Wipf P, Reno MJ, Williams DR. Org. Lett. 2000; 2: 1165
    • 15a Goddard-Borger ED, Stick RV. Org. Lett. 2007; 9: 3797
    • 15b Nyffeler PT, Liang C-H, Koeller KM, Wong C-H. J. Am. Chem. Soc. 2002; 124: 10773
  • 16 Wipf P, Miller CP, Venkatraman S, Fritch PC. Tetrahedron Lett. 1995; 36: 6395
  • 17 Fuchs PL, Corey EJ. Tetrahedron Lett. 1972; 13: 3769
  • 18 He R, Chen Y, Chen Y, Ougolkov AV, Zhang J, Savoy DN, Billadeau DD, Kozikowski AP. J. Med. Chem. 2010; 53: 1347
  • 19 Chattopadhyay SK, Pal BK, Biswas S. Synth. Commun. 2005; 35: 1167
  • 20 Ferreira PM, Monteiro LS, Pereira G, Ribeiro L, Sacramento J, Silva S. Eur. J. Org. Chem. 2007; 5934
  • 21 Sellanes D, Campot F, Núñez I, Lin G, Espósito P, Dematteis S, Saldaña J, Domínguez L, Manta E, Serra G. Tetrahedron 2010; 66: 5384
  • 22 Huh DH, Jeong JS, Lee HB, Ryu H, Kim YG. Tetrahedron 2002; 58: 9925
  • 23 Kundu NG, Khan MW. Tetrahedron 2000; 56: 4777
  • 24 Gupton JT, Telang N, Banner EJ, Kluball EJ, Hall KE, Finzel KL, Jia X, Bates SR, Welden RS, Giglio BC, Eaton JE, Barelli PJ, Firich LT, Stafford JA, Coppock MB, Worrall EF, Kanters RP. F, Keertikar K, Osterman R. Tetrahedron 2010; 66: 9113
  • 25 Shimada N, Hanari T, Kurosaki Y, Anada M, Nambu H, Shiro M, Hashimoto S. J. Org. Chem. 2010; 75: 6039
  • 26 Schmittel M, Morbach G, Schenk WA, Hagel M. J. Chem. Crystallogr. 2005; 35: 373