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

Guillermo Valdomir; Juan I. Padrón; José M. Padrón; Víctor S. Martín; Danilo Davyt

doi:10.1055/s-0033-1339139

Synthesis, Table of Contents

Synthesis 2014; 46(18): 2451-2462
DOI: 10.1055/s-0033-1339139

paper

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

Guillermo Valdomir

^aCátedra 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

^bInstituto de Productos Naturales y Agrobiología, CSIC, C/ Astrofísico Francisco Sánchez 3, 38206 La Laguna, Spain

^cInstituto 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

^cInstituto 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

^cInstituto 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*

^aCátedra 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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Abstract

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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.

Key words

alkynes - azides - heterocycles - peptides - ring closure

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References

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

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