Design and synthesis of a potential SH2 domain inhibitor bearing a stereodiversified 1,4-cis-enediol scaffold

Tetrahedron

Volumn 67, Issue 52, 2011, Pages 10216-10221

  Marian, Christine ^a   Huang, Rong ^a,b   Borch, Richard F ^a  

^a PURDUE UNIVERSITY   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Alkynylation; cis Enediol; SH2 domain; Stereodiversified

Indexed keywords

(2 BENZYL 3 HYDROXYPENT 4 YNOYL) 4 METHYL 5 PHENYLOXAZOLIDIN 2 ONE; 2 [4 [(DI TERT BUTOXYPHOSPHORYL)OXY]PHENYL]ACETIC ACID; 4 [2 [(6 BENZYL 2,5,7 TRIHYDROXYHEPT 3 EN 1 YL)AMINO] 2 OXOETHYL]PHENYL DIHYDROGEN PHOSPHATE; 4 [2 [[6 BENZYL 2,5,7 TRIS[(TERT BUTYLDIMETHYLSILYL)OXY]HEPT 3 EN 1 YL]AMINO] 2 OXOETHYL]PHENYL DI TERT BUTYL PHOSPHATE; 5 BENZYL 4 ETHYNYL 2,2 DIMETHYL 1,3 DIOXANE; ENEDIOL DERIVATIVE; KETONE; METHYL 2 [4 [(DI TERT BUTOXYPHOSPHORYL)OXY]PHENYL]ACETATE; PROTEIN SH2; PROTEIN TYROSINE KINASE INHIBITOR; TERT BUTYL 2 [METHOXY(METHYL)AMINO] 2 OXOETHYLCARBAMATE; TERT BUTYL 4 (5 BENZYL 2,2 DIMETHYL 1,3 DIOXAN 4 YL) 2 OXOBUT 3 YNYLCARBAMATE; TERT BUTYL [4 (5 BENZYL 2,2 DIMETHYL 1,3 DIOXAN 4 YL) 2 HYDROXYBUT 3 EN 1 YL]CARBAMATE; TERT BUTYL [4 (5 BENZYL 2,2 DIMETHYL 1,3 DIOXAN 4 YL) 2 HYDROXYBUT 3 YN 1 YL]CARBAMATE; TERT BUTYL [6 BENZYL 2,5,7 TRIS[(TERT BUTYLDIMETHYLSILYL)OXY]HEPT 3 EN 1 YL]CARBAMATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYNYLATION; ARTICLE; ASYMMETRIC CATALYSIS; BINDING AFFINITY; CHEMICAL REACTION; CHIRALITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTEIN DOMAIN; REPRODUCIBILITY; STEREOCHEMISTRY; TECHNIQUE;

EID: 82255162538     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.014     Document Type: Article

References (23)

1. T. Hunter Cell 100 2000 113 127
2. A. Levitzki Acc. Chem. Res. 36 2003 462 469
3. J. Schlessinger, and M.A. Lemmon Sci. STKE 191 2003 1 12
4. K. Machida, and B.J. Mayer Biochim. Biophys. Acta 1747 2005 1 25
5. S. Zhou, S.E. Shoelson, M. Chaudhuri, G. Gish, T. Pawson, W.G. Haser, F. King, T. Roberts, S. Ratnofsky, R.J. Lechleider, B.G. Neel, R.B. Birge, J.E. Fajardo, M.M. Chou, H. Hanafusa, B. Schaffhausen, and L.C. Cantley Cell 72 1993 767 778
6. T.R. Burke, and K. Lee Acc. Chem. Res. 36 2003 426 433
7. L. Tong, T.C. Warren, J. King, R. Betageri, J. Rose, and S. Jakes J. Mol. Biol. 256 1996 601 610
8. W.C. Shakespeare Curr. Opin. Chem. Biol. 5 2001 409 415
9. T.K. Sawyer, R.S. Bohacek, D.C. Dalgarno, C.J. Eyermann, K. Noriyuki, C.A. Metcalf, W.C. Shakespeare, R. Sundaramoorthi, Y. Wang, and M.G. Yang Mini-Rev. Med. Chem. 2 2002 475 488
10. H. Garrido-Hernandez, K.D. Moon, R.L. Geahlen, and R.F. Borch J. Med. Chem. 49 2006 3368 3376
11. J.E. DeLorbe, J.H. Clements, M.G. Teresk, A.P. Benfield, H.R. Plake, L.E. Millspaugh, and S.F. Martin J. Am. Chem. Soc. 131 2009 16758 16770
12. B.A. Harrison, T.M. Gierasch, C. Neilan, G.W. Pasternak, and G.L. Verdine J. Am. Chem. Soc. 124 2002 13352 13353
13. M. Llinas-Brunet, P.L. Beaulieu, D.R. Cameron, J.-M. Ferland, J. Gauthier, E. Ghiro, J. Gillard, V. Gorys, M. Poirier, J. Rancourt, and D. Wernic J. Med. Chem. 42 1999 722 729
14. E.A. Lunney, K.S. Para, J.R. Rubin, C. Humblet, J.H. Fergus, J.S. Marks, and T.K. Sawyer J. Am. Chem. Soc. 119 1997 12471 12476
15. T.M. Gierasch, M. Chytil, M.T. Didiuk, J.Y. Park, J.J. Urban, S.P. Nolan, and G.L. Verdine Org. Lett. 2 2000 3999 4002
16. D.A. Evans, J.V. Nelson, and T.R. Taber Stereoselective Aldol Condensations Topics in Stereochemistry Vol. 13 1982 John Wiley & Sons Inc. Hoboken, New Jersey, USA pp 1-115
17. A. Abiko, J. Liu, and S. Masamune J. Am. Chem. Soc. 119 1997 2586 2587
18. J.R. Gage, and D.A. Evans Org. Synth. Collect. Vol. 8 1993 528
19. Org. Synth. 68 1990 77
20. K. Matsumura, S. Hashiguchi, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 119 1997 8738 8739
21. T.R. Hoye, C.S. Jeffrey, and F. Shao Nat. Protocols 2 2007 2451 2458
22. C. Gomez, J. Chen, and S. Wang Tetrahedron Lett. 50 2009 6691 6692
23. T. Morwick, M. Hrapchak, M. DeTuri, and S. Campbell Org. Lett. 4 2002 2665 2668