Synthesis of an Enkephalin Analogue Containing an α,α-Disubstituted Heterocyclic Aminophosphonic Acid

REFERENCES

• Galeazzi , R. , Martelli , G. , Marcucci , E. , Orena , M. , Rinaldi , S. , Lattanzi , R. and Negri , L. 2010 . Amino Acids , 38 : 1057 – 1065 .
   Google Scholar
• Toth , F. , Farkas , J. , Toth , G. , Wollemann , M. , Borsodi , A. and Benyhe , S. 2003 . Peptides , 24 : 1433 – 1440 .
   Google Scholar
• Siemion , I. Z. , Klis , W. A. and Nawrocka , E. 1981 . Pol. J. Chem. , 55 : 2219 – 2222 .
   Google Scholar
• Lee , Y. S. , Petrov , R. , Park , C. K. , Ma , S.-W. , Davis , P. , Lai , J. , Porreca , F. , Vardanyan , R. and Hruby , V. J. 2007 . J. Med. Chem. , 50 : 5528 – 5532 .
   Google Scholar
• Kupczyk-Subotkowaska , L. and Mastalerz , P. 1983 . Int. J. Peptide Protein Res. , 21 : 485 – 490 .
   Google Scholar
• Kukhar , V. P. and Hudson , H. R. 2000 . Aminophosphonic and Aminophosphinic Acids , New York, NY : Wiley .
   Google Scholar
• For a review on stereoselective synthesis of α-aminophosphonic acids, see: , Ordonez , M. , Rojas-Cabrera , H. and Cativiela , C. 2009 . Tetrahedron , 65 : 17 – 49 .
   Google Scholar
• Mastalerz , P. , Kupczyk-Subotkowska , L. , Herman , Z. S. and Laskawie , G. 1982 . Naturwissenschaften , 69 : 46 – 47 .
   PubMed Web of Science ®Google Scholar
• Bien , E. and Herman , Z. S. 1986 . Acta Pol. Pharm. , 43 : 176 – 179 .
   Google Scholar
• Hruby , V. J. and Gehrig , C. A. 1989 . Med. Res. Rev. , 9 : 343 – 401 .
   PubMed Web of Science ®Google Scholar
• DiMaio , J. , Nguyen , T. M. D. , Lemieux , C. and Schiller , P. W. 1982 . J. Med. Chem. , 25 : 1432 – 1438 .
   PubMedGoogle Scholar
• Ronai , A. Z. , Szekely , J. I. , Berzetei , I. , Miglecz , E. and Bajusz , S. 1979 . Biochem. Biophys. Res. Commun. , 91 : 1239 – 1249 .
   Google Scholar
• Kodama , H. , Uchida , H. , Yasunaga , T. , Kondo , M. , Costa , T. and Shimohigashin , Y. 1990 . J. Mol. Recognit. , 3 : 197 – 203 .
   Google Scholar
• Bajusz , S. , Ronai , A. Z. , Szekely , J. I. , Turan , A. , Juhasz , A. , Patthy , A. , Miglecz , E. and Berzetei , I. 1980 . FEBS Lett. , 117 : 308 – 310 .
   PubMed Web of Science ®Google Scholar
• Ohfune , Y. and Shinada , T. 2005 . Eur. J. Org. Chem. , : 5127 – 5143 .
   Google Scholar
• Kang , S. H. , Kang , S. Y. , Lee , H.-S. and Buglass , A. J. 2005 . Chem. Rev. , 105 : 4537 – 4558 .
   Google Scholar
• Fadel , A. 1999 . J. Org. Chem. , 64 : 4953 – 4955 .
   Google Scholar
• Fadel , A. and Tesson , N. 2000 . Eur. J. Org. Chem. , : 2153 – 2159 .
   Google Scholar
• Tesson , N. , Dorigneux , B. and Fadel , A. 2002 . Tetrahedron: Asymmetry , 13 : 2267 – 2276 .
   Google Scholar
• Rabasso , N. , Louaisil , N. and Fadel , A. 2006 . Tetrahedron , 62 : 7445 – 7454 .
   Web of Science ®Google Scholar
• Louaisil , N. , Rabasso , N. and Fadel , A. 2007 . Synthesis , : 289 – 293 .
   Google Scholar
• Rabasso , N. and Fadel , A. 2008 . Synthesis , : 2353 – 2362 .
   Google Scholar
• Louaisil , N. , Rabasso , N. and Fadel , A. 2009 . Tetrahedron , 65 : 8587 – 8595 .
   Web of Science ®Google Scholar
• Kafarski , P. and Lejczak , B. 1989 . Tetrahedron , 45 : 7387 – 7396 .
   Web of Science ®Google Scholar
• Kafarski , P. and Mastalerz , S. 1977 . Roczniki Chem , 51 : 433 – 437 .
   Web of Science ®Google Scholar
• Gilmore , W. F. and McBride , M. A. 1974 . J. Pharm. Sci. , 63 : 1087 – 1090 .
   PubMed Web of Science ®Google Scholar
• Olsen , R. K. and Ramasamy , K. 1985 . J. Org. Chem. , 50 : 2264 – 2271 .
   Google Scholar
• Hansen , D. W. and Pilipauskas , D. 1985 . J. Org. Chem. , 50 : 945 – 950 .
   Web of Science ®Google Scholar
• Fauchere , J. L. , Leukert , O. , Eberle , A. and Schwyzer , R. 1979 . Helv. Chim. Acta , 62 : 1385 – 1395 .
   Web of Science ®Google Scholar
• Jones , D. A. , Schlatter , J. M. , Mikulec , R. A. and Reuter , J. A. Ger. Patent, DE 1977-2735699 , Chemical Abstract No. 1978, 89, 44246
   Google Scholar
• Pless , J. and Cardinaux , F. Ger. Patent, DE 1977-2655149 , Chemical Abstract No. 1977, 87, 168423
   Google Scholar