Efficient microwave assisted syntheses of 2,5-diketopiperazines in aqueous media

Molecules

Volumn 14, Issue 8, 2009, Pages 2836-2849

  Pérez Picaso, Lemuel ^a   Escalante, Jaime ^a   Olivo, Horacio F ^b   Rios, María Yolanda ^a  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

2,5 diketopiperazines; Cyclic dipeptides; DKPs; Microwave irradiation

Indexed keywords

CYCLOPEPTIDE; ESTER; PIPERAZINEDIONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

DIKETOPIPERAZINES; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MICROWAVES; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC;

EID: 69549105621     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14082836     Document Type: Article

References (41)

1. Wipf, P. Synthetic studies of biologically active marine cyclopeptides. Chem. Rev. 1995, 95, 2115-2134.
2. Amidon, G.L.; Lee, H.J. Absorption of peptide and peptidomimetic drugs. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 321-341.
3. Liu, S.; Gu, W.; Lo, D.; Ding, X.; Ujiki, M.; Adrian, T.E.; Soff, G.A.; Silverman, R.B. N-Methylsansalvamide A peptide analogues. Potent new antitumor agents. J. Med. Chem. 2005, 48, 3630-3638.
4. Prasad, C. Bioctive cyclic dipeptides. Peptides 1995, 16, 151-164.
5. Houston, D.R.; Synstad, B.; Eijsink, V.G.H.; Stark, M.J.R.; Eggleston, I.M.; van Aalten, D.M.F. Structure-based exploration of cyclic dipeptide chitinase inhibitors. J. Med. Chem. 2004, 47, 5713-5720.
6. Martins, M.B.; Carvalho, I. Diketopiperazines: biological activity and synthesis. Tetrahedron 2007, 63, 9923-9932.
7. Graz, C.J.M.; Grant, G.D.; Brauns, S.C.; Hunt, A.; Jamie, H.; Milne, P.J. Cyclic dipeptides in the induction of maturation for cancer therapy. J. Pharm. Pharmacol. 2000, 52, 75-82.
8. Prakash, K.R.C.; Tang, Y.; Kozikowski, A.P.; Flippen-Anderson, J.L.; Knoblach, S.M.; Faden, A.I. Synthesis and biological activity of novel neuroprotective diketopiperazines. Bioorg. Med. Chem. 2002, 10, 3043-3048.
9. Lambert, J.N.; Mitchell, J.P.; Roberts, K.D. The synthesis of cyclic peptides. J. Chem. Soc. Perkin Trans. I 2001, 471-484.
10. Rajappa, S.; Natekar, M.V. Piperazine-2,5-diones and related lactam ethers. Adv. Het. Chem. 1993, 57, 187-289.
11. Fischer, P.M.J. Diketopiperazines in peptide and combinatorial chemistry. J. Pept. Sci. 2003, 9, 9-35.
12. Dinsmore, C.J.; Beshore, D.C. Recent advances in the synthesis of diketopiperazines. Tetrahedron 2002, 58, 3297-3312.
13. Rodionov, I.L.; Rodionova, L.N.; Baidakova, L.K.; Romashko, A.M.; Balashova, T.A.; Ivanov, V.T. Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines. Tetrahedron 2002, 58, 8515-8523.
14. Fischer, E. Synthese von polypeptiden. Chem. Ber. 1906, 39, 2893-2931.
15. Ueda, T.; Saito, M.; Kato, T.; Izumiya, N. Facile Synthesis of Cyclic Dipeptides and Detection of Racemization. Bull. Chem. Soc. Jpn. 1983, 56, 568-572.
16. Suzuki, K.; Sasaki, Y.; Endo, N.; Mihara, Y. Acetic acid-catalized diketopiperazine synthesis. Chem. Pharm. Bull. 1981, 29, 233-237.
17. Nitecki, D.E.; Halpern, B.; Westley, J.W. Simple route to sterically pure dioxopiperazines. J. Org. Chem. 1968, 33, 864-866.
18. Eriksson, J.; Arvidsson, P.I.; Davidsson, O. Solution structure of a dilithiumamide/diethylzinc heterocomplex that catalyzes asymmetric alkylation reactions. Chem. Eur. J. 1999, 5, 2356-2361.
19. Lee, S.; Kanmera, T.; Aoyagi, H.; Izumiya, N. Cyclic peptides. VI. Asymmetric hydrogenation of dehydroalanine or dehydroaminobutanoic acid residue in cyclodipeptides. Int. J. Pept. Protein Res. 1979, 13, 207-217.
20. Kappe, C.O.; Dallinger, D. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature. Mol. Divers. 2009, 13, 71-193.
21. Kappe, C.O.; Dallinger, D.; Murphree, S.S. Practical microwave synthesis for organic chemists: Strategies, Instruments, and Protocols, 1st ed.; Wiley-VCH: Darmstadt, Germany, 2009.
22. Santagada, V., Fiorino, F.; Perissutti, E.; Severino, B.; Terracciano, S.; Cirino, G.; Caliendo, G. A convenient strategy of dimerization by microwave heating and using 2,5-diketopiperazine as scaffold. Tetrahedron Lett. 2003, 44, 1145-1148.
23. López-Cobeñas, A.; Cledera, P.; Sánchez, J.D.; Pérez-Contreras, R.; López-Alvarado, P.; Ramos, M.T.; Avendaño, C.; Menéndez, J.C. Solvent-Free, Efficient Synthesis of 2,5-Piperazinediones from Boc-protected dipeptide esters under microwave irradiation. Synlett 2005, 7, 1158-1160.
24. Tullberg, M.; Grøtli, M.; Luthman, K. Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating. Tetrahedron 2006, 62, 7484-7491.
25. Jam, F.; Tullberg, M.; Luthman, K.; Grøtli, M. Microwave assisted synthesis of spiro-2,5-diketopiperazines. Tetrahedron 2007, 63, 9881-9889.
26. Fischer, P.M.; Solbakken, M.; Undheim, K. Solution synthesis of a dimeric pentapeptide: diketopiperazine cyclisation of Glu-Asp dipeptide esters and Asp-racemisation during segment condensation. Tetrahedron 1994, 50, 2277-2288.
27. Besser, D.; Greiner, G.; Reissmann, S. Side reaction with N-carboxymethyl amino acids in the synthesis of lactone cyclized peptides. Lett. Pept. Sci. 1998, 5, 299-303.
28. Pérez-Picaso, L.; Rios, M.Y.; Hernández, A.N.; Martínez, J. 1H and 13C assignments of cyclo [N-(Lys-Phe)-Orn-Val], a semicyclic imide tetrapeptide from Burkholderia cepacia. Magn. Reson. Chem. 2006, 44, 959-961.
29. Pandey, S.K.; Awasthi, K.K.; Saxena, A.K. Microwave assisted stereospecific synthesis of (S)-3-substituted 2,3,6,7,12,12a- hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-diones. Tetrahedron 2001, 57, 4437-14432.
30. Kobayashi, N.; Higuchi, T.; Urano, Y.; Kikuchi, K.; Hirobe, M.; Nagano, T. Dipeptides Containing L-arginine analogs: New isozyme-selective inhibitors of nitric oxide synthase. Biol. Pharm. Bull. 1999, 22, 936-940.
31. Shen, H.Y.; Tian, G.L.; Ye, Y.H.; Wang, J. Non-coded amino acids as acyl donor substrates for peptide bond formation catalyzed by thermoase in toluene. J. Mol. Catal. B-Enzym. 2005, 37, 26-29.
32. Dineen, T.A.; Zajac, M.A.; Myers, A.G. Efficient transamidation of primary carboxamides by in situ activation with N,N-dialkylformamide dimethyl acetals. J. Am. Chem. Soc. 2006, 128, 16406-16409.
33. Izumiya, N.; Kato, T.; Fujita, Y.; Ohno, M.; Kondo, M. Studies of peptide antibiotics, I. Dipeptide anhydrides as models of cyclic peptide antibiotics. Bull. Chem. Soc. Jpn. 1964, 37, 1809-1816.
34. López-Cobeñas, A.; Cledera, P.; Sánchez, J.D.; López-Alvarado, P.; Ramos, M.T.; Avendaño, C.; Menéndez, J.C. Microwave-assisted synthesis of 2,5-piperazinediones under solvent-free conditions. Synthesis 2005, 19, 3412-3422.
35. Huang, H.; She, Z.; Lin, Y.; Vrijmoed, L.L.P.; Lin, W. Cyclic Peptides from an Endophytic Fungus Obtained from a Mangrove Leaf (Kandelia candel). J. Nat. Prod. 2007, 70, 1696-1699.
36. Joshi, K.B., Verma, S. Participation of aromatic side chains in diketopiperazine ensembles. Tetrahedron Lett. 2008, 49, 4231-4234.
37. Tullberg, M.; Luthman, K.; Grøtli, M. Microwave-assisted solid-phase synthesis of 2,5-diketopiperazines: Solvent and resin dependence. J. Comb. Chem. 2006, 8, 915-922.
38. Bull, S.D.; Davies, S.G.; Moss, W.O. Practical synthesis of Schöllkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5- dimethoxy-3-isopropyl-pyrazine. Tetrahedron: Asym. 1998, 9, 321-327.
39. Cledera, P.; Avendaño, C.; Menéndez, J.C. Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones. Tetrahedron 1998, 54, 12349-12360.
40. Tanihara, M.; Hiza, T.; Imanishi, Y.; Higashimura, T. Solution conformation of cyclic dipeptides having aliphatic side chains. Bull. Chem. Soc. Jpn. 1983, 56, 1155-1160.
41. Lucente, G.; Pinnen, F.; Zanotti, G. Cyclization of activated N-benzyloxycarbonyl-tripeptides. Tetrahedron Lett. 1978, 11, 1009-1012.