Design and synthesis of new bicyclic diketopiperazines as scaffolds for receptor probes of structurally diverse functionality

Organic and Biomolecular Chemistry

Volumn 3, Issue 10, 2005, Pages 2016-2025

  Besada, Pedro ^a   Mamedova, Liaman ^a   Thomas, Craig J ^a   Costanzi, Stefano ^a   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ENZYMES; ETHERS; MOLECULAR STRUCTURE; SCAFFOLDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BICYCLIC DIKETOPIPERAZINES; METATHESIS REACTION; NATURAL PRODUCTS; RECEPTOR PROBES;

AROMATIC COMPOUNDS;

BICYCLO COMPOUND; PIPERAZINE DERIVATIVE; PIPERAZINEDIONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; ELECTROCHEMISTRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

BICYCLO COMPOUNDS; DIMERIZATION; ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PIPERAZINES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 19944373483     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416349d     Document Type: Article

References (46)

1. R. M. Williams and C. A. Durham, Bicyclomycin: synthetic, mechanistic, and biological studies, Chem Rev., 1988, 88, 511-540.
2. Y. Funabashi, T. Horiguchi, S. Iinuma, S. Tanida and S. Harada, TAN-1496 A, C and E, diketopiperazine antibiotics with inhibit activity against mammalian DNA topoisomerase I, J. Antibiot., 1994, 47, 1202-18.
3. J. Moyroud, J. Gelin, A. Chene and J. Mortier, Synthese d'analogues structuraux de Thaxtomines, phytotoxines responsables de la gale de la pomme de terre, Tetrahedron, 1996, 52, 8525-8534.
4. A. K. Szardenings and T. S. Burkoth, A simple procedure for the solid phase synthesis of diketopiperazine and diketomorpholine derivatives, Tetrahedron, 1997, 53, 6573-6593.
5. J. Alsina, K. J. Jensen, F. Albericio and G. Barany, Solid-phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL), Chem. Eur. J., 1999, 5, 2787-2795.
6. E. Perrotta, M. Altamura, T. Barani, S. Bindi, D. Giannotti, N. J. S. Harmat, R. Nannicini and C. A. Maggi, 2,6-Diketopiperazines from amino acids, from solution-phase to solid-phase organic synthesis, J. Comb. Chem., 2001, 3, 453-460.
7. C. J. Dinsmore and D. C. Beshore, Recent advances in the synthesis of diketopiperazines, Tetrahedron, 2002, 58, 3297-3312.
8. T. Guo, G. Dong, D. Fitzpatrick, P. Geng, K. K. Ho, C. H. Jibilian, S. G. Kultgen, R. Liu, E. McDonald, K. W. Saionz, K. J. Valenzano, D. Xie, A. E. P. Adang, N. C. R. van Straten, M. L. Webb, Discovery of potent biaryl diketopiperazine FSH receptor agonists: rapid lead optimization through parallel synthesis Poster of the 228th ACS National Meeting, Philadelphia, PA, 2004.
9. A. K. Szardenings, D. Harris, S. Lam, L. Shi, D. Tien, Y. Wang, D. V. Patel, M. Navre and D. A. Campbell, Rational design and combinatorial evaluation of enzyme inhibitor scaffolds: identification of novel inhibitors of matrix metalloproteinases, J. Med. Chem., 1998, 41, 2194-2200.
10. A. K. Szardenings, V. Antonenko, D. A. Campbell, N. DeFrancisco, S. Ida, L. Shi, N. Sharkov, D. Tien, Y. Wang and M. Navre, Identification of highly selective inhibitors of collagenase-1 from combinatorial libraries of diketopiperazines, J. Med. Chem., 1999, 42, 1348-1357.
11. A. Bianco, C. P. Sonksen, P. Roepstorff and J.-P. Briand, Solid-phase synthesis and structural characterization of highly substituted hydroxyproline-based 2,5-diketopiperazines, J. Org. Chem., 2000, 65, 2179-2187.
12. A. Bianco, J. Furrer, D. Limal, G. Guichard, K. Elbayed, J. Raya, M. Piotto and J.-P. Briand, Multistep synthesis of 2,5-diketopiperazines on different solid supports monitored by high resolution magic angle spinning NMR spectroscopy, J. Comb. Chem., 2000, 2, 681-690.
13. A. N. Koehler, A. F. Shamji and S. L. Schreiber, Discovery of an inhibitor of a transcription factor using small molecule microarrays and diversity-oriented synthesis, J. Am. Chem. Soc, 2003, 125, 8420-8421.
14. K. Shokat and M. Velleca, Novel chemical genetic approaches to the discovery of signal transduction inhibitors, Drug Discov. Today, 2002, 7, 872-879.
15. C. J. Creighton, G. C. Leo, Y. Du and A. B. Reitz, Design, synthesis, and conformational analysis of eight-membered cyclic peptidomimetics prepared using ring closing metathesis, Bioorg. Med. Chem., 2004, 12, 4375-4385.
16. M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Synthesis and activity of a new generation of ruthenium-basedolefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands, Org. Lett., 1999, 1, 953-956.
17. S. J. Connon and S. Blechert, Recents developments in olefin cross-metathesis, Angew. Chem., Int. Ed., 2003, 42, 1900-1923.
18. I. von Kügelgen and A. Wetter, Molecular pharmacology of P2Y-receptors, Naunyn Schmiedebergs Arch. Pharmacol., 2000, 362, 310-323.
19. B. F. King and A. Townsend-Nicholson, Recombinant P2Y receptors: the UCL experience, J. Auton. Nerv. Syst, 2000, 81, 164-170.
20. G. Hollopeter, H. M. Jantzen, D. Vincent, G. Li, L. England, V. Ramakrishnan, R. B. Yang, P. Nurden, A. Nurden, D. Julius and P. B. Conley, Identification of the platelet ADP receptor targeted by antithrombotic drugs, Nature, 2001, 409, 202-207.
21. i, J. Biol. Chem., 2001, 276, 41 479-41 485.
22. K. A. Jacobson, Purine and pyrimidine nucleotide (P2) receptors, Ann. Rep. Med. Chem., 2002, 37, 75-84.
23. 1 receptor antagonists and partial agonists, J. Med. Chem., 1999, 42, 1625-1638.
24. 1 receptor ligands, J. Med. Chem., 2000, 43, 829-842.
25. 1 receptor: structure activity relationships and receptor docking, J. Med. Chem., 2001, 44, 3092-3108.
26. 1 receptor antagonist, Br. J. Pharmacol, 2002, 135, 2004-2010.
27. B. Fischer, J. L. Boyer, C. H. V. Hoyle, A. U. Ziganshin, A. L. Brizzolara, G. E. Knight, J. Zimmet, G. Burnstock, T. K. Harden and K. A. Jacobson, Identification of potent, selective P2Y-purinoceptor agonists: structure-activity relationships for 2-thioether derivatives of adenosine 5′-triphosphate, J. Med. Chem., 1993, 36, 3937-3946.
28. 2Y purinoceptor agonists that are derivatives of adenosine 5′-monophosphate, Br. J. Pharmacol., 1996, 118, 1959-1964.
29. B. Fischer, A. Chulkin, J. L. Boyer, K. T. Harden, F. P. Gendron, A. R. Beaudoin, J. Chapal, D. Hillaire-Buys and P. Petit, 2-Thioether 5′-O-(1-thiotriphosphate)adenosine derivatives as new insulin secre tagogues acting through P2Y-Receptors, J. Med. Chem., 1999, 42, 3636-3646.
30. 1 purinergic receptor: synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques, J. Med. Chem, 2002, 45, 962-972.
31. 1-receptor antagonists, J. Org. Chem, 2002, 67, 8063-8071.
32. 2T receptor: a novel approach to antithrombotic therapy, J. Med Chem, 1999, 42, 213-220.
33. 4 nucleotide receptors, Biochem. Pharmacol., 2003, 65, 923-931.
34. M. P. Glenn, L. K. Pattenden, R. C. Reid, D. P. Tyssen, J. D. A. Tyndall, C. J. Birch and D. P. Fairlie, β-Strand mimicking macrocyclic amino acids: templates for protease inhibitors with antiviral activity. J. Med. Chem., 2002, 45, 371-381.
35. I. Koch and M. Keusgen, Diastereoselective synthesis of alliin by an asymmetric sulfur oxidation, Pharmazie, 1998, 53, 668-671.
36. C. G. Boojamra, K. M. Burow, L. A. Thompson and J. A. Ellman, Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality, J. Org. Chem., 1997, 62, 1240-1256.
37. K. J. Jensen, J. Alsina, M. F. Songster, J. Vagner, F. Albericio and G. Barany, Backbone amide linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides, J. Am. Chem. Soc., 1998, 120, 5441-5452.
38. M. Fresno, J. Alsina, M. Royo, G. Barany and F. Albericio, Solid-phase synthesis of diketopiperazine, useful scaffolds for combinatorial chemistry, Tetrahedron Lett., 1998, 39, 2639-2642.
39. 1 receptor with a high affinity radiolabeled antagonist, Mol. Pharmacol., 2002, 62, 1249-1257.
40. M. Ohno, S. Costanzi, H. S. Kim, V. Kempeneers, K. Vastmans, P. Herdewijn, S. Maddileti, Z. G. Gao, T. K. Harden and K. A. Jacobson, Nucleotide analogues containing 2-oxa-bicyclo[2.2.1]heptane and L-α-threofuranosyl ring rystems: interactions with P2Y receptors, Bioorg. Med. Chem., 2004, 12, 5619-5630.
41. S. Costanzi, L. Mamedova, Z.-G. Gao and K. A. Jacobson, Architecture of P2Y nucleotide receptors: structural comparison based on sequence analysis, mutagenesis, and homology modeling, J. Med. Chem., 2004, 47, 5393-5404.
42. L. Wang, S. E. W. Jacobsen, A. Bengtsson and D. Erlinge, P2 receptor mRNA expression profiles in human lymphocytes, monocytes and CD34+ stem and progenitor cells, BMC Immunol., 2004, 5, 16.
43. J. K. Chambers, L. E. Macdonald, H. M. Sarau, R. S. Ames, K. Freeman, J. J. Foley, Y. Zhu, M. M. McLaughlin, P. Murdock, L. McMillan, J. Trill, A. Swift, N. Aiyar, P. Taylor, L. Vawter, S. Naheed, P. Szekeres, G. Hervieu, C. Scott, J. M. Watson, A. J. Murphy, E. Duzic, C. Klein, D. J. Bergsma, S. Wilson and G. P. Livi, A G protein-coupled receptor for UDP-glucose. J. Biol. Chem., 2000, 275, 10 767-10 771.
44. M. M. Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding, Anal. Biochem., 1976, 76, 248-254.
45. J. R. Maple, M. J. Hwang, T. P. Stockfisch, U. Dinur, M. Waldman, C. S. Ewig and A. T. Hagler, Derivation of Class II force fields. 1. Methodology and quantum force field for the alkyl functional group and alkane molecules, J. Comput. Chem., 1994, 15, 162-182.
46. C. A. G. Haasnoot, Conformational analysis of six-membered rings in solution: ring-puckering coordinates derived from vicinal NMR proton-proton coupling constants, J. Am. Chem. Soc., 1993, 115, 1460-1468.