Synthesis and library construction of privileged tetra-substituted Δ5-2-oxopiperazine as β-turn structure mimetics

ACS Combinatorial Science

Volumn 16, Issue 1, 2014, Pages 24-32

  Kim, Jonghoon ^a   Lee, Won Seok ^a   Koo, Jaeyoung ^a   Lee, Jeongae ^a   Park, Seung Bum ^a  

^a Seoul National University   (South Korea)

Author keywords

5 2 oxopiperazine; library construction; mimetics; synthesis

Indexed keywords

AMINO ACID; PIPERAZINE DERIVATIVE; PROTEIN;

BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

AMINO ACIDS; BIOMIMETICS; COMBINATORIAL CHEMISTRY TECHNIQUES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; PROTEINS;

EID: 84892622231     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co400128a     Document Type: Article

References (51)

1. Hopkins, A. L.; Groom, C. R. The druggable genome Nat. Rev. Drug Discovery 2002, 1, 727-730
2. Strausberg, R. L.; Schreiber, S. L. From knowing to controlling: a path from genomics to drugs using small molecule probes Science 2003, 300, 294-295
3. Schreiber, S. L. Small molecules: the missing link in the central dogma Nat. Chem. Biol. 2005, 1, 64-66
4. Sekhon, B. S. Chemical biology: Past, present and future Curr. Chem. Biol. 2008, 2, 278-311
5. Zheng, X. F. S.; Chan, T.-F. Chemical genomics in the global study of protein functions Drug Discovery Today 2002, 7, 197-205
6. Newman, D. J.; Cragg, G. M.; Sander, K. M. Natural products as sources of new drugs over the Period 1981-2002 J. Nat. Prod. 2003, 66, 1022-1037
7. Newman, D. J.; Cragg, G. M. Natural products as sources of new drugs over the last 25 years J. Nat. Prod. 2007, 70, 461-477
8. Drewy, D. H.; Macarron, R. Enhancements of screening collections to address areas of unmet medical need: an industry perspective Curr. Opin. Chem. Biol. 2010, 14, 289-298
9. Bleicher, K. H.; Böhm, H.-J.; Muller, K.; Alanine, A. A guide to drug discovery: hit and lead generation: Beyond high-throughput screening Nat. Rev. Drug Discovery 2003, 2, 369-378
10. Dandapani, S.; Marcaurelle, L. A. Grand challenge commentary: Accessing new chemical space for 'undruggable' targets Nat. Chem. Biol. 2010, 6, 861-863
11. Dai, W.-M. Generation of molecular shape diversity. From privileged scaffolds to diverted total synthesis Diversity Oriented Synthesis 2013, 1, 11-20
12. Galloway, W. R.; Spring, D. R. Towards drugging the 'undruggable': Enhancing the scaffold diversity of synthetic small molecule screening collections using diversity-oriented synthesis Diversity Oriented Synthesis 2013, 1, 21-28
13. Galloway, W. R.; Llobert, A. I.; Spring, D. R. Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules Nat. Commun. 2010, 1, 80
14. Tan, D. S. Diversity-oriented synthesis: Exploring the intersections between chemistry and biology Nat. Chem. Biol. 2005, 1, 74-84
15. Spandl, R. J.; Bender, A.; Spring, D. R. Diversity-oriented synthesis; a spectrum of approaches and results Org. Biomol. Chem. 2008, 6, 1149-1158
16. Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery Science 2000, 287, 1964-1968
17. Ko, S. K.; Jang, H. J.; Kim, E.; Park, S. B. Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif Chem. Commun. 2006, 28, 2962-2964
18. Oh, S.; Cho, S. W.; Yang, J. Y.; Snu, H. J.; Chung, Y. S.; Shin, C. S.; Park, S. B. Discovery of a novel benzopyranyl compound as a potent in vitro and in vivo osteogenic agent Med. Chem. Commun. 2011, 2, 76-80
19. Zhu, M.; Kim, M. H.; Lee, S.; Kim, S. H.; Park, S. B. Discovery of novel benzopyranyl tetracycles that act as inhibitors of osteoclastogenesis induced by receptor activator of NF-κB ligand J. Med. Chem. 2010, 53, 8760-8764
20. Oh, S.; Kim, S. J.; Hwang, J. H.; Lee, H. Y.; Ryu, M. J.; Park, J.; Kim, S. J.; Jo, Y. S.; Kim, Y. K.; Lee, C. H.; Kweon, K. R.; Shong, M.; Park, S. B. Antidiabetic and antiobesity effects of ampkinone (6f), a novel small molecule activator of AMP-activated protein kinase J. Med. Chem. 2010, 53, 7405-7413
21. Oh, S.; Nam, H. J.; Park, J.; Beak, S. H.; Park, S. B. Development of a benzopyran-containing androgen receptor antagonist to treat antiandrogen- resistant prostate cancer ChemMedChem. 2010, 5, 529-533
22. Koh, M.; Park, S. B. Computer-aided design and synthesis of tetra-aryl-substituted alkenes and their bioevaluation as a selective modulator of estrogen related receptor γ Mol. Diversity 2011, 15, 69-81
23. Lee, S. C.; Park, S. B. Novel application of Leuckart-Wallach reaction for synthesis of tetrahydro-1,4-benzodiazepin-5-ones library Chem. Commun. 2007, 9, 825-835
24. Park, S.; Kim, J.; Koh, M.; Park, S. B. Efficient parallel synthesis of privileged benzopyranylpyrazoles via regioselective condensation of β-keto aldehydes with hydrazines J. Comb. Chem. 2009, 11, 315-326
25. Lee, S.; Park, S. B. An efficient one-step synthesis of heteroiaryl pyrazolo[3,4-b]pyridines via indole ring opening Org. Lett. 2009, 11, 5214-5217
26. Kim, J.; Song, H.; Park, S. B. Orthogonal regioselective synthesis of N -alkyl-3-substituted tetrahydroindazolones Eur. J. Org. Chem. 2010, 20, 3815-3822
27. Kim, J.; Song, H.; Park, S. B. Solid-phase parallel synthesis of tetrahydroindazolone library containing three unique core skeletons Chem. -Asian. J. 2011, 6, 2062-2072
28. Song, H.; Lee, H.; Kim, J.; Park, S. B. Regioselective construction and screening of 1,3-disubstituted tetrahydroindazolones in enantiomerically pure pairs ACS Comb. Sci. 2012, 14, 66-74
29. Oh, S.; Park, S. B. A design strategy for drug-like polyheterocycles with privileged substructures for discovery of specific small-molecule modulators Chem. Commun. 2011, 47, 12754-12761
30. Bhatt, U.; Mohamed, N.; Just, G.; Roberts, E. Derivatized oxopiperazine rings from amino acids Tetrahedron Lett. 1997, 38, 3679-3682
31. DiMaio, J.; Belleau, B. Synthesis of chiral piperazin-2-ones as model peptidomimetics J. Chem. Soc., Perkin Trans. 1 1989, 9, 1687-1689
32. Okada, Y.; Takeuchi, H.; Yokoi, T. Total synthesis of optically active deoxyaspergillic acid from dipeptidyl aldehyde Tetrahedron Lett. 1996, 37, 2249-2252
33. Whitby, L. R.; Boger, D. L. Comprehensive peptidomimetic libraries targeting protein-protein Interactions Acc. Chem. Res. 2012, 45, 1698-1709
34. Arkin, M. R.; Welles, J. A. Small-molecule inhibitors of protein-protein interactions: progressing towards the dream Nat. Rev. Drug Discovery 2004, 3, 301-317
35. Garland, S. L.; Dean, P. M. Design criteria for molecular mimics of fragments of the β-turn. 1. Cα atom analysis J. Comput. Aided Mol. Des. 1999, 13, 469-483
36. Eguchi, M. Recent advances in selective opioid receptor agonists and antagonists Med. Res. Rev. 2004, 24, 182-212
37. Fichna, J.; Costentin, A.; Rego, J. C. D. The endomorphin system and its evolving neurophysiological role Pharmacol. Rev. 2007, 59, 88-123
38. Tomboly, C.; Ballet, S.; Feytens, D.; Kover, K. E.; Borics, A.; Lovas, S.; Al-Khrasani, M.; Furst, Z.; Toth, G.; Benyhe, S.; Tourwe, D. Endomorphin-2 with a β-turn backbone constraint retains the potent μ-opioid receptor agonist properties J. Med. Chem. 2008, 51, 173-177
39. Eguchi, M.; Shen, R. Y.; Shea, J. P.; Lee, M. S.; Kahn, M. Design, synthesis, and evaluation of opioid analogues with non-peptidic β-turn scaffold: enkephalin and endomorphin mimetics J. Med. Chem. 2002, 45, 1395-1398
40. Sugihara, H.; Fukushi, H.; Miyawaki, T.; Imai, Y.; Terashita, Z.; Kawamura, M.; Fusisawa, Y.; Kita, S. Novel non-peptide fibrinogen receptor antagonists. 1. Synthesis and glycoprotein IIb-IIIa antagonistic activities of 1,3,4-trisubstituted 2-oxopiperazine derivatives incorporating side-chain functions of the RGDF peptide J. Med. Chem. 1998, 41, 489-502
41. Horwell, D. C.; Lewthwaite, R. A.; Pritchard, M. C.; Ratcliffe, G. S.; Rubin, J. R. The use of heterocycles for the conformational restriction of biologically active peptoids Tetrahedron 1998, 54, 4591-4606
42. Kitamura, S.; Fukushi, H.; Miyawaki, T.; Kawamura, M.; Komishi, N.; Terashita, Z.; Naka, T. Potent dibasic GPIIb/IIIa antagonists with reduced prolongation of bleeding time: synthesis and pharmacological evaluation of 2-oxopiperazine derivatives J. Med. Chem. 2001, 44, 2438-2450
43. Askew, B. C., Jr.; Aya, T.; Biswas, K.; Cai, G.; Chen, J. J.; Han, N.; Liu, Q.; Nguyen, T.; Nishimura, N.; Nomak, R.; Peterkin, T.; Qian, W. 1,2,3,4-Tetrahydropyrazin-2-yl acetamides and their use as bradykinin antagonists for the treatment of inflammation related disorders. WO2006019975, February 23, 2006.
44. Aya, T.; Cai, G.; Chen, J. J.; D'amico, D. C.; Nguyen, T.; Qian, W. Triazoles and their use as bradykinin B1 receptor antagonists. WO2006044355, April 27, 2006.
45. Peng, H.; Carrico, D.; Thai, V.; Blaskovich, M.; Bucher, C.; Pusateri, E. E.; Sebti, S. M.; Hamilton, A. D. Synthesis and evaluation of potent, highly-selective, 3-aryl-piperazinone inhibitors of protein geranylgeranyltransferase-I Org. Biomol. Chem. 2006, 4, 1768-1784
46. 5-2-oxopiperazines via N -acyliminium ions cyclization Tetrahedron Lett. 2002, 43, 6293-6295
47. 5-2-oxopiperazines via N -acyliminium ion cyclization J. Comb. Chem. 2007, 9, 828-835
48. Cho, T. J.; Kim, J.; Kwon, S. K.; Oh, K.; Lee, J. A.; Lee, D. S.; Lee, D. S.; Cho, J.; Park, S. B. A potent small-molecule inducer of chondrogenic differentiation of human bone marrow-derived mesenchymal stem cells Chem. Sci. 2012, 3, 3071-3075
49. Suat Kee, K.; Jois Seetharma, D. S. Design of β-turn based therapeutic agents Curr. Pharm. Des. 2003, 9, 1209-1224
50. Guruprasad, K.; Rajkumar, S. β- and γ-turns in proteins revisited: a new set of amino acid turn-type dependent positional preferences and potentials J. Biosci. 2000, 25, 143-156
51. Garland, S. L.; Dean, P. M. Design criteria for molecular mimics of fragments of the beta-turn. 2. C-alpha-C-beta bond vector analysis J. Comput. Aided Mol. Des. 1999, 13, 485-498