Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
169
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Simple and Mild One-Pot Synthesis of Dipeptidyl Ureas via Carbamoyl Azides of α-N-Protected Amino Acids

, &
Pages 1027-1041 | Received 26 Jan 2010, Published online: 03 Mar 2011

REFERENCES

  • (a) Spatola , A. F. Peptide backbone modifications: A structure–activity analysis of peptides containing amide bond surrogates, conformational constraints, and replacement . In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins ; B. Weinstein (Ed.); Marcel Dekker : New York , 1983 ; vol. 7 ; pp. 267 – 357 ; (b) Siman , R. J. ; Kania , R. S. ; Zuuckermann , R. N. ; Huebner , V. D. ; Jewell , D. A. ; Banville , S. ; Ng , S. ; Wang , L. ; Rosenberg , S. ; Marlowe , C. K. ; Bartlett , P. A. Peptoids: A modular approach to drug discovery. Proc. Natl. Acad. Sci. USA 1992, 89, 9367–9371; (c) Zuckermann , R. N. ; Kerr , J. M. ; Kent , S. B. ; Moos , W. H. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 1992, 114, 10646–10647; (d) Cho , C. Y. ; Moran , E. J. ; Cherry , S. R. ; Stephans , J. C. ; Fodor , S. P. A. ; Adams , C. L. ; Sundaram , A. ; Jacobs , J. W. ; Schultz , P. G. An unnatural biopolymer. Science 1993, 261, 1303–1305; (e) Kessler , H. Peptoids—A new approach to the development of pharmaceuticals. Angew. Chem., Int. Ed. Engl. 1993, 32, 543–544; (f) Giannis , A. Peptidomimetics for receptor ligands discovery, development, and medical perspectives. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244–1267; (g) Gante , J. Peptidomimetics—Tailored enzyme inhibitors. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699–1720; (h) Liskamp , R. M. J. Opportunities for new chemical libraries—Unnatural biopolymers and diversomers. Angew. Chem., Int. Ed. Engl. 1994, 33, 633–636; (i) Moran , E. J. ; Wilson , T. E. ; Cho , C. Y. ; Cherry , S. R. ; Schultz , P. G. Novel biopolymers for drug discovery. Biopolymers 1995, 37, 213–219; (j) Kruijtzer , J. A. W. ; Liskamp , R. M. J. Synthesis in solution of peptoids using Fmoc-protected N-substituted glycines. Tetrahedron Lett. 1995, 36, 6969–6972; (k) Sawyer , T. K. In Peptide-Based Drug Design Controlling Transport and Metabolism ; M. D. Taylor , G. L. Amidorn (Eds.); Oxford University Press : New York , 1995 ; pp. 332 – 422 ; (l) Nowick , J. S. ; Smith , E. M. ; Pairish , M. Artificial β-sheets. Chem. Soc. Rev. 1996, 25, 401–415; (m) Seebach , D. ; Matthews , J. L. β-Peptides: A surprise at every turn. Chem. Commun. 1997, 2015–2022; (n) Gellman , S. H. Foldamers: A manifesto. Acc. Chem. Res. 1998, 31, 173–180; (o) Wender , P. A. ; Mitchell , D. J. ; Pattabiram , K. ; Pelkey , E. T. ; Steinman , L. ; Rothbard , J. B. The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters. Proc. Natl. Acad. Sci. USA 2000, 97, 13003–13008; (p) Cheng , R. P. ; Gellman , S. H. ; De-Grado , W. F. β-Peptides: From structure to function. Chem. Rev. 2001, 101, 3219–3232; (q) Hill , D. J. ; Mio , M. J. ; Prince , R. B. ; Hughes , T. S. ; Moore , J. S. A field guide to foldamers. Chem. Rev. 2001, 101, 3893–4011; (r) Patch , J. A. ; Barron , A. E. Mimicry of bioactive peptides via non-natural, sequence-specific peptidomimetic oligomers. Curr. Opin. Chem. Biol. 2002, 6, 872–877; (s) Seebach , D. ; Beck , A. K. ; Bierbaum , D. J. The world of β- and γ-peptides comprised of homologated proteinogenic amino acids and other components. Chem. Biodiversity 2004, 1, 1111–1239; (t) Guichard , G. β-Peptides, γ-peptides and isoteric backbones: New scaffolds with controlled shapes for mimicking protein secondary structure elements. In Pseudopeptides in Drug Development ; P. E. Nielsen (Ed.); Wiley-VCH : Weinheim , Germany , 2004 , pp. 33 – 120 ; (u) Kritzer , J. A. ; Stephens , O. M. ; Guarracino , D. A. ; Reznik , S. K. ; Schepartz , A. β-Peptides as inhibitors of protein–protein interactions. Bioorg. Med. Chem. 2005, 13, 11–16.
  • (a) Eichmann , K. Transmembrane signaling of lymphocytes-T by ligand-induced receptor complex assembly. Angew. Chem., Int. Ed. Engl. 1993, 32, 54–63; (b) Lam , P. Y. ; Jadhav , P. K. ; Eyermann , C. J. ; Hodge , C. N. ; Ru , Y. ; Bacheler , L. T. ; Meek , J. L. ; Otto , M. J. ; Rayner , M. M. ; Wong , Y. N. ; Chang , C.-H. ; Weber , P. C. ; Jackson , D. A. ; Sharpe , T. R. ; Erickson-Viitanen , S. Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science 1994, 263, 380–384; (c) Burgess , K. ; Linthicum , D. S. ; Shin , H. Solid-phase syntheses of unnatural biopolymers containing repeating urea units. Angew. Chem., Int. Ed. Engl. 1995, 34, 907–909; (d) Hutchins , S. M. ; Chapman , K. T. A strategy for urea linked diamine libraries. Tetrahedron Lett. 1995, 36, 2583–2586; (e) von Geldern , T. W. ; Kesster , J. A. ; Bal , R. ; Wu-Wong , J. R. ; Chiou , W. ; Dixon , D. B. ; Opgenorth , T. J. Azole endothelin antagonists, 2: Structure–activity studies. J. Med. Chem. 1996, 36, 968–981; (f) Castro , J. L. ; Ball , R. G. ; Broughton , H. B. ; Russell , M. G. N. ; Rathbone , D. ; Watt , A. P. ; Baker , R. ; Chapman , K. L. ; Fletcher , A. E. ; Patel , S. ; Smith , A. J. ; Marshall , G. R. ; Ryecroft , W. ; Matassa , V. G. Controlled modification of acidity in cholecystokinin B receptor antagonists: N-(1,4-Benzodiazepin-3-yl)-N′-[3-(tetrazol-5-ylamino)phenyl]ureas. J. Med. Chem. 1996, 39, 842–849; (g) Kim , J. M. ; Bi , Y. ; Paikoff , S. J. ; Schultz , P. G. The solid-phase synthesis of oligoureas. Tetrahedron Lett. 1996, 37, 5305–5308; (h) Burgess , K. ; Ibarzo , J. ; Linthicum , D. S. ; Russell , D. H. ; Shin , H. ; Shitangkoon , A. ; Totani , R. ; Zhang , A. J. Solid-phase syntheses of oligoureas. J. Am. Chem. Soc. 1997, 119, 1556–1564; (i) Kruijtzer , J. A. W. ; Lefeber , D. J. ; Liskamp , R. M. J. Approaches to the synthesis of urea peptoid peptidomimetics. Tetrahedron Lett. 1997, 38, 5335–5338; (j) Holmes , D. L. ; Smith , E. M. ; Nowick , J. S. Solid-phase synthesis of artificial β-sheets. J. Am. Chem. Soc. 1997, 119, 7665–7669; (k) Fletcher , M. D. ; Campbell , M. M. Partially modified retro-inverso peptides: Development, synthesis, and conformational behavior. Chem. Rev. 1998, 98, 763–795; (l) Nowick , J. S. Chemical models of protein β-sheets. Acc. Chem. Res. 1999, 32, 287–296; (m) Tamilarasu , N. ; Huq , I. ; Rana , T. M. High affinity and specific binding of HIV-1 TAR RNA by a Tat-derived oligourea. J. Am. Chem. Soc. 1999, 121, 1597–1598; (n) Boeijen , A. ; Liskamp , R. M. J. Solid-phase synthesis of oligourea peptidomimetics. Eur. J. Org. Chem. 1999, 2127–2135; (o) Guichard , G. ; Semetey , V. ; Didierjean , C. ; Aubry , A. ; Briand , J. P. ; Rodriguez , M. Effective preparation of O-succinimidyl-2(tert-butoxycarbonylamino) ethylcarbamate derivatives from β-amino acids: Application to the synthesis of urea-containing pseudopeptides and oligoureas. J. Org. Chem. 1999, 64, 8702–8705; (p) Guichard , G. ; Semetey , V. ; Rodriguez , M. ; Briand , J. P. Solid-phase synthesis of oligoureas using O-succinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers. Tetrahedron Lett. 2000, 41, 1553–1557; (q) Kozikowski , A. P. ; Zhang , J. ; Nan , F. ; Petukhov , P. A. ; Grajkowska , E. ; Wroblewski , J. T. ; Yamamoto , T. ; Bzdega , T. ; Wroblewska , B. ; Neale , J. H. Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: Efficacy as analgesic agents. J. Med. Chem. 2004, 47, 1729–1738; (r) Lena , G. ; Lallemand , E. ; Gruner , A. C. ; Boeglin , J. ; Roussel , S. ; Schaffner , A.-P. ; Aubry , A. ; Franetich , J.-F. ; Mazier , D. ; Landau , I. ; Briand , J.-P. ; Didierjean , C. ; Renia , L. ; Guichard , G. 1,3,5-Triazepan-2,6-diones as structurally diverse and conformationally constrained dipeptide mimetics: Identification of malaria liver stage inhibitors from a small pilot library. Chem. Eur. J. 2006, 12, 8498–8512; (s) Muller , P. ; Lena , G. ; Boilard , E. ; Bezzine , S. ; Lambeau , G. ; Guichard , G. ; Rognan , D. In silico-guided target identification of a scaffold-focused library: 1,3,5-Triazepan-2,6-diones as novel phospholipase A2 inhibitors. J. Med. Chem. 2006, 49, 6768–6778.
  • (a) Vegners , R. ; Chipens , G. Synthesis and study of angiotensin II analogs containing vasopressin structural elements . Tezisy Dokl.-Vses. Simp. Khim. Pept. Belkov. 1974 , 28 ; (b) Vegners , R. ; Chipens , G. Synthesis of [1-glycinamide, 2-carbonylarginine]angiotensin II, analog of angiotensin II, containing C-terminal dipeptide of arginine-vasopression . Zh. Obshch. Khim. 1975 , 45 , 444 – 449 .
  • Kawasaki , K. ; Maeda , M. ; Watanabe , J. ; Keneto , H. Amino acids and peptides, IX.: Synthetic studies on Leu-Enkephalin analogues containing a ureylene bond . Chem. Pharm. Bull. 1988 , 36 , 1766 – 1771 .
  • Rodriguez , M. ; Dubreuil , P. ; Bali , J. P. ; Martinez , J. Synthesis and biological activity of partially modified retro-inverso pseudopeptide derivatives of the C-terminal tetrapeptide of gastrin . J. Med. Chem. 1987 , 30 , 758 – 763 .
  • (a) Wlodawer , A. ; Miller , M. ; Jaskolski , M. ; Sathyanarayana , B. K. ; Baldwin , E. ; Weber , I. T. ; Selk , L. M. ; Clawson , L. ; Schneider , J. ; Kent , S. B. H. Conserved folding in retroviral proteases: Crystal structure of a synthetic HIV-1 protease. Science 1989, 245, 616–621; (b) Navia , M. A. ; Fitzgerald , P. M. D. ; McKeever , B. M. ; Leu , C.-T. ; Heimbach , J. C. ; Herber , W. K. ; Sigal , I. S. ; Darke , P. L. ; Springer , J. P. Three-dimensional structure of aspartyl protease from human immunodeficiency virus HIV-1. Nature 1989, 337, 615–620; (c) Stefanelli , S. ; Cavaletti , L. ; Sarubbi , E. ; Ragg , E. ; Colombo , L. ; Selva , E. GE20372 factor-A and factor-B: New HIV-1 protease inhibitors, produced by Streptomyces sp. ATCC-55925. J. Antibiot. 1995, 48, 332–334; (d) Brik , A. ; Wong , C.-H. HIV-1 protease: Mechanism and drug discovery. Org. Biomol. Chem. 2003, 1, 5–14; (e) Myers , A. C. ; Kowalski , J. A. ; Lipton , M. A. Facile incorporation of urea pseudopeptides into protease substrate analogue inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 5219–5222; (f) Barth , B. S. ; Myers , A. C. ; Lipton , M. A. Exploring the stereochemical requirements for protease inhibition by ureidopeptides. J. Pept. Res. 2005, 65, 352–354.
  • (a) Getman , D. P. ; de Crescenzo , G. A. ; Heintz , R. M. ; Reed , K. L. ; Talley , J. J. ; Bryant , M. L. ; Clare , M. ; Houseman , K. A. ; Marr , J. J. ; Mueller , R. A. Discovery of a novel class of potent HIV-1 protease inhibitors containing the (R)-(hydroxyethyl) urea isostere . J. Med. Chem. 1993 , 36 , 288 – 291 ; (b) Esler , W. P. ; Kimberly , W. T. ; Ostaszewski , B. L. ; Ye , W. ; Diehl , T. S. ; Selkoe , D. J. ; Wolfe , M. S. Activity-dependent isolation of the presenilin-γ-secretase complex reveals nicastrin and a γ-substrate . Proc. Natl. Acad. Sci. USA 2002 , 99 , 2720 – 2725 ; (c) Bakshi , P. ; Wolfe , M. S. Stereochemical analysis of (hydroxyethyl)urea peptidomimetic inhibitors of γ-secretase . J. Med. Chem. 2004 , 47 , 6485 – 6489 ; (d) Esler , W. P. ; Das , C. ; Wolfe , M. S. Probing pockets S2-S4′ of the γ-secretase active site with (hydroxyethyl)urea peptidomimeties . Bioorg. Med. Chem. Lett. 2004 , 14 , 1935 – 1938 .
  • Kick , E. K. ; Ellman , J. A. Expedient method for the solid-phase synthesis of aspartic-acid protease inhibitors directed toward the generation of libraries . J. Med. Chem. 1995 , 38 , 1427 – 1430 .
  • Dales , N. A. ; Bohacek , R. S. ; Satyshur , K. A. ; Rich , D. H. Design and synthesis of unsymmetrical peptidyl urea inhibitors of aspartic peptidases . Org. Lett. 2001 , 3 , 2313 – 2316 .
  • (a) Kaneto , R. ; Chiba , H. ; Dobashi , K. ; Kojima , I. ; Sasaki , K. ; Shibamoto , N. ; Nishida , H. ; Okamoto , R. ; Akagawa , H. ; Mizuno , S. J. MER-N5075A, a potential HIV-1 protease inhibitor, produced by Streptomyces chromofuscus . J. Antibiot. 1993 , 46 , 1622 – 1624 ; (b) Zhang , X. ; Rodrigues , J. ; Evans , L. ; Hinkle , B. ; Ballantyne , L. ; Pena , M. Formation of urea dipeptides from carbonyldiimidazole: Application toward the protease inhibitors GE 20372 and MAPI . J. Org. Chem. 1997 , 62 , 6420 – 6423 ; (c) Broadbridge , R. J. ; Sharma , R. P. ; Akhtar , M. First efficient synthesis of α-MAPI . Chem. Commun. 1998 , 1449 – 1450 .
  • Guerlavais , V. ; Boeglin , D. ; Mousseaux , D. ; Oiry , C. ; Heitz , A. ; Deghenghi , R. ; Locatelli , V. ; Torsello , A. ; Ghe , C. ; Catapano , F. ; Muccioli , G. ; Galleyrand , J. C. ; Fehrentz , J. A. ; Martinez , J. New active series of growth hormone secretagogues . J. Med. Chem. 2003 , 46 , 1191 – 1203 .
  • Patil , B. S. ; Suresh Babu , V. V. Synthesis of peptidyl ureas employing O-pentafluorophenyl-(9-fluorenylmethoxycarbonylamino)methyl carbamate derivatives . Lett. Pept. Sci. 2003 , 10 , 93 – 97 .
  • Suresh Babu , V. V. ; Kantharaju , K. 2,4,5-Trichlorophenyl-(9H-fluoren-9-ylmethoxycarbonylamino)methylcarbamates: Synthesis, isolation, characterization, and utility in the synthesis of dipeptidyl ureas . Ind. J. Chem. 2005 , 44B , 1046 – 1053 .
  • (a) Patil , B. S. ; Suresh Babu , V. V. A rapid synthesis of dipeptidyl urea acids employing p-nitrophenyl-(9-fluorenylmethoxycarbonylamino)methyl carbamates . Ind. J. Chem. 2004 , 43B , 1721 – 1728 ; (b) Patil , B. S. ; Vasanthakumar , G.-R. ; Suresh Babu , V. V. Synthesis of peptidyl ureas using p-nitrophenyl-(9-fluorenylmethoxycarbonylamino)methyl carbamate derivatives . Synth. Commun. 2004 , 34 , 2313 – 2321 .
  • Fischer , L. ; Semetey , V. ; Lozano , J.-M. ; Schaffner , A.-P. ; Briand , J.-P. ; Didierjean , C. ; Guichard , G. Succinimidyl carbamate derivatives from N-protected α-amino acids and dipeptides—Synthesis of ureidopeptides and oligourea/peptide hybrids. Eur. J. Org. Chem. 2007, 2511–2525.
  • (a) Suresh Babu , V. V. ; Ananda , K. ; Vasanthakumar , G.-R. (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid azides: Synthesis, isolation, characterisation, stability, and application to synthesis of peptides . J. Chem. Soc., Perkin Trans. 1 2000 , 4328 – 4331 ; (b) Patil , B. S. ; Vasanthakumar , G.-R. ; Suresh Babu , V. V. Isocyanates of N α -[(9-fluorenylmethyl)oxy]carbonyl amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of urea peptidomimetics . J. Org. Chem. 2003 , 68 , 7274 – 7280 ; (c) Sureshbabu , V. V. ; Patil , B. S. ; Venkataramanarao , R. Preparation, isolation, and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas . J. Org. Chem. 2006 , 71 , 7697 – 7705 .
  • Suresh Babu , V. V. ; Sudarshan , N. S. ; Naik , S. A. Synthesis of ureidopeptides and peptidyl ureas employing Bsmoc chemistry . Int. J. Pept. Res. Ther. 2008 , 14 , 105 – 112 .
  • Sureshbabu , V. V. ; Chennakrishnareddy , G. ; Narendra , N. A facile and one-pot synthesis of N α -Fmoc/Bsmoc/Boc/Z-protected ureidopeptides and peptidyl ureas employing diphenylphosphoryl azide [DPPA] . Tetrahedron Lett. 2008 , 49 , 1408 – 1412 .
  • (a) Radhakrishna , A. S. ; Parham , M. E. ; Riggs , R. M. ; Loudon , G. M. New method for direct conversion of amides to amines . J. Org. Chem. 1979 , 44 , 1746 – 1747 ; (b) Boutin , R. H. ; Loudon , G. M. Conversion of aliphatic amides into amines with [1,1-bis(trifluoroacetoxy)iodo]benzene, 2: Kinetics and mechanism . J. Org. Chem. 1984 , 49 , 4277 – 4284 ; (c) Englund , E. A. ; Gopi , H. N. ; Appella , D. H. An efficient synthesis of a probe for protein function: 2,3-Diaminopropionic acid with orthogonal protecting groups . Org. Lett. 2004 , 6 , 213 – 215 .
  • Narendra , N. ; Chennakrishnareddy , G. ; Sureshbabu , V. V. Application of carbodiimide-mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidyl ureas employing N-urethane α-amino/peptidyl hydroxamic acids . Org. Biomol. Chem. 2009 , 7 , 3520 – 3526 .
  • Verardo , G. ; Bombardella , E. ; Geatti , P. ; Strazzolini , P. Carbamoyl azides of α-N-protected amino acids: A fast and simple one-pot synthesis . Synthesis 2008 , 438 – 444 .
  • Verardo , G. ; Bombardella , E. ; Venneri , C. D. ; Strazzolini , P. A convenient synthesis of unsymmetrical substituted ureas via carbamoyl azides of α-N-protected amino acids . Eur. J. Org. Chem. 2009 , 6239 – 6244 .
  • Williams , D. H. ; Fleming , I. In Spectroscopic Methods in Organic Chemistry, , 6th ed. ; McGraw-Hill Education : London , 2008 ; pp. 77 – 78 .
  • (a) Chen , F. M. F. ; Benoiton , N. L. Diisopropylethylamine eliminates dipeptide formation during the acylation of amino acids using benzoyl chloride and some alkyl chloroformates . Can. J. Chem. 1987 , 65 , 1224 – 1227 ; (b) Vogel , A. In Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman Scietific & Technical: New York, 1989, pp. 762 and 786.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.