Synthesis of arginine-containing hydroxamate dipeptidomimetics

Tetrahedron Letters

Volumn 47, Issue 24, 2006, Pages 4069-4073

  Seo, Jiwon ^a   Silverman, Richard B ^a  

^a The Center for Drug Discovery and Chemical Biology ^*  (United States)

Author keywords

Acid chloride; Arginine; Hydroxamate; Peptidomimetics

Indexed keywords

ARGININE DERIVATIVE; GAMMA LACTAM DERIVATIVE; N ALPHA (9 FLUORENYLMETHYLOXYCARBONYL)ARGININE; PEPTIDE; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; LOW TEMPERATURE; MOLECULAR INTERACTION; PHASE SEPARATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS;

EID: 33646354382     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.190     Document Type: Article

References (27)

1. Peterlin-Masic L., and Kikelj D. Tetrahedron 57 (2001) 7073-7105
2. Grillo M.A., and Colombatto S. Amino Acids 26 (2004) 345-351
3. Kerwin Jr. J.F., Lancaster Jr. J.R., and Feldman P.L. J. Med. Chem. 38 (1995) 4342-4362
4. Erdal E.P., Litzinger E.A., Seo J., Zhu Y., Ji H., and Silverman R.B. Curr. Top. Med. Chem. 5 (2005) 603-624
5. Leung D., Abbenante G., and Fairlie D.P. J. Med. Chem. 43 (2000) 305-341
6. Semple J.E., Levy O.E., Minami N.K., Owens T.D., and Siev D.V. Bioorg. Med. Chem. Lett. 10 (2000) 2305-2309
7. Leung D., Schroder K., White H., Fang N., Stoermer M.J., Abbenante G., Martin J.L., Young P.R., and Fairlie D.P. J. Biol. Chem. 276 (2001) 45762-45771
8. Gómez-Vidal J.A., and Silverman R.B. Org. Lett. 3 (2001) 2481-2484
9. Gómez-Vidal J.A., Forrester M.T., and Silverman R.B. Org. Lett. 3 (2001) 2477-2479
10. HBTU/HOBt/DIEA, HATU/DIEA, BOP/DIEA, PyBOP/DIEA.
11. Examples of BOP/DIEA system for hydroxamate coupling:. Dong L., and Miller M.J. J. Org. Chem. 67 (2002) 4759-4770
12. Bergeron R.J., Liu C.Z., McManis J.S., Xia M.X.B., Algee S.E., and Wiegand J. J. Med. Chem. 37 (1994) 1411-1417
13. +] = 301.7.
14. Reagent abbreviations used: PyBroP = bromo-tris-pyrrolidinophosphonium hexafluorophosphate; DIEA = N,N-diisopropylethylamine; TFFH = fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate; EDC = N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide; HATU = O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate; HBTU = O-benzotriazole-N,N,N′,N′-tetramethyluronium hexafluorophosphate; HOBt = 1-hydroxybenzotriazole; BOP = benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate; PyBOP = benzotriazole-1-yl-oxy-tris-(pyrrolidino)-phosphonium.
15. Coste J., Frerot E., and Jouin P. J. Org. Chem. 59 (1994) 2437-2466
16. Carpino L.A., and El-Faham A. J. Am. Chem. Soc. 117 (1995) 5401-5402
17. Brundish D., Bull A., Donovan V., Fullerton J.D., Garman S.M., Hayler J.F., Janus D., Kane P.D., McDonnell M., Smith G.P., Wakeford R., Walker C.V., Howarth G., Hoyle W., Allen M.C., Ambler J., Butler K., and Talbot M.D. J. Med. Chem. 42 (1999) 4584-4603
18. Rutenber E.E., De Voss J.J., Hoffman L., Stroud R.M., Lee K.H., Alvarez J., MePhee F., Craik C., and Ortiz de Montellano P.R. Bioorg. Med. Chem. 5 (1997) 1311-1320
19. Inouye K., Sasaki A., and Yoshida N. Bull. Chem. Soc. Jpn. 47 (1974) 202-203
20. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley & Sons, New York p 603
21. Milburn R.R., and Snieckus V. Angew. Chem., Int. Ed. 43 (2004) 892-894
22. Hofmann K., Peckham W.D., and Rheiner A. J. Am. Chem. Soc. 78 (1956) 238-242
23. Carpino L.A., Cohen B.J., Stephens Jr. K.E., Sadat-Aalaee Y., Tien J., and Langridge D.C. J. Org. Chem. 51 (1986) 3732-3734
24. Wang L., and Phanstiel IV O. J. Org. Chem. 65 (2000) 1442-1447
25. Romine J.L. Org. Prep. Proced. Int. 28 (1996) 249-288
26. Carpino L.A., Ghassemi S., Ionescu D., Ismail M., Sadat-Aalaee D., Truran G.A., Mansour E.M.E., Siwruk G.A., Eynon J.S., and Morgan B. Org. Process Res. Dev. 7 (2003) 28-37
27. +] = 794.4.