A facile one-pot synthesis of N α-urethane protected 3-amino alkyl isoxazole-5-carboxylic acids and their utility for the preparation of isoxazole-linked peptidomimetics

International Journal of Peptide Research and Therapeutics

Volumn 17, Issue 3, 2011, Pages 185-191

  Chennakrishnareddy, G ^a   Vasantha, B ^a   Narendra, N ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

2+3 cycloaddition; Click chemistry; Isoxazole; N protected amino aldehyde; Nitrile oxide; One pot synthesis; Peptidomimetics

Indexed keywords

3 AMINO ALKYL ISOXAZOLE 5 CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER; ISOXAZOLE DERIVATIVE; N ALPHA URETHANE; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG; URETHAN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CLICK CHEMISTRY; CYCLOADDITION; DRUG STRUCTURE; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 83255185258     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-011-9256-x     Document Type: Article

References (37)

1. Andre I, Alcazar J, Alonso JM, Lucas AID, Iturrino L, Biesmansb I, MegensAA(2006) Synthesis of 7-amino-3a,4-dihydro-3H-[1]benzopyrano[ 4,3-c]isoxazole derivatives displaying combined a2-adrenoceptor antagonistic and 5-HT reuptake inhibiting activities. Bioorg Med Chem 14:4361-4372 (Pubitemid 44250769)
2. Annunziata R, Cinquini M, Cozzi F, Gennari C, Raimondi L (1987) Stereoselectivity of intramolecular nitrile oxide cycloadditions to Z and E chiral alkenes. J Org Chem 52:4674-4681
3. Bailey TR, Diana GD, Kowalczyk PJ, Akullian V, Eissenstatrt MA, Cutcliffe D, Mallamo JP, Carabateas PM, Pevear DC (1992) Antirhinoviral activity of heterocyclic analogs of Win 54954. J Med Chem 35:4628-4633 (Pubitemid 23006682)
4. Cheng J-F, Mjalli AMM (1998) Solid-phase synthesis of D2-isoxazolines. Tetrahedron Lett 39:939-942
5. Chiang YH (1971) Chlorination of oximes. Reaction and mechanism of the chlorination of oximes in commercial chloroform and methylene chloride. J Org Chem 36:2146-2155
6. Cho CY, Moran EJ, Cherry SR, Stephans JC, Fodor SPA, Adams CL, Sundaran A, Jacobs JW, Schultz PG (1993) An unnatural biopolymer. Science 261:1303-1305 (Pubitemid 24082271)
7. Chung YJ, Ryu EJ, Keum G, Kim BH (1996) Synthesis of 2-isoxazoline and a- hydroxy ketomethylene dipeptide isosteres. Bioorg Med Chem 4:209-225 (Pubitemid 26109315)
8. Cuadrado P, Gonzalez-Nogal AM, Valero R (2002) Regiospecific synthesis of 5-silyl azoles. Tetrahedron 58:4975-4980 (Pubitemid 34628857)
9. Easton CJ, Hughes M, Tiekink ERT (1994) Reversal of regiochemistry in the synthesis of isoxazoles by nitrile oxide cycloadditions. Tetrahedron Lett 35:3589-3592 (Pubitemid 24176493)
10. Ebert B, Lenz S, Brehm L, Bregnedal P, Hansen JJ, Frederiksen K, Bogeso KP, Krogsgaard-Larsen P (1994) Resolution, absolute stereochemistry, and pharmacology of the S-(?)- and R-(-)- isomers of the apparent partial AMPA receptor agonist (R, S)-2- amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R, S)-APPA]. J Med Chem 37:878-884 (Pubitemid 24140856)
11. Elkasaby MA, Salem MAI (1980) Synthesis of new isoxazoles from isoxazolines, chalkones, chalkone dibromides, epoxides and acetylated ketoximes and their conversion into novel heterocycles. Indian J Chem Section B 19B:571-575
12. Gennari C, Salom B, Potenza D, Williams A (1994) Synthesis of sulfonamido- pseudopeptides: new chiral unnatural oligomers. Angew Chem Int Ed Engl 33:2067-2069 (Pubitemid 24987680)
13. Goodman M, Felix A, Moroder L, Toniolo C (eds) (2003) Synthesis of peptides and peptidomimetics (Houben-Weyl), vol E22c. George Thieme Verlag, Stuttgart
14. Grunanger P, Vita-Finzi P (eds) (2008) Chemistry of heterocyclic compounds: isoxazoles, Part 1, vol 49. Wiley Interscience, New York
15. Hansen TV, Wu P, Fokin VV (2005) One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles. J Org Chem 70: 7761-7764 (Pubitemid 41318540)
16. Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J Am Chem Soc 127:210-216 (Pubitemid 40094384)
17. Huisgen R (1976) 1,3-Dipolar cycloadditions. 76. Concerted nature of 1,3-dipolar cycloadditions and the question of diradical intermediates. J Org Chem 41:403-419
18. Jones R.C.F., Ward GJ (1988) Amide bond isosteres: imidazolines in pseudopeptide chemistry. Tetrahedron Lett 29:3853-3856
19. Kantorowski EJ, Kurth MJ (1997) Solid-phase synthesis of isoxazoles and isoxazolines: en route to a new class of ionophores. J Org Chem 62:6797-6803 (Pubitemid 127494614)
20. Kim BH, Chung YJ, Keum G, Kim J, KimK(1992)Anew peptide bond surrogate: 2- isoxazoline in pseudopeptide chemistry. Tetrahedron Lett 33:6811-6814
21. Kim BH, Chung YJ, Ryu EJ (1993) Synthesis of a-hydroxy ketomethylene dipeptide isosteres. Tetrahedron Lett 34:8465-8468 (Pubitemid 24043419)
22. Liu K-C, Shelton BR, Howe RK (1980) A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors). J Org Chem 45:3916-3918
23. Luca LD, Giacomelli G, Riu A (2001) Solid-phase synthesis of isoxazole-based amino acids: a new scaffold for molecular diversity. J Org Chem 66:6823-6825 (Pubitemid 32946609)
24. Myers AG, Zhong B, Movassaghi M, Kung DW, Lanman BA, Kwon S (2000) Synthesis of highly epimerizable N-protected a-amino aldehydes of high enantiomeric excess. Tetrahedron Lett 41: 1359-1362 (Pubitemid 30126515)
25. Norman BH, Lander PA, Gruber JM, Kroin JS, Cohen JD, Jungheim LN, Starling JJ, Law KL, Self TD, Tabas LD, Williams DC, Paul DC, Dantzig AH (2005) Cyclohexyl-linked tricyclic isoxazoles are potent and selective modulators of the multidrug resistance protein (MRP1). Bioorg Med Chem Lett 15:5526-5530 (Pubitemid 41562984)
26. Patil BS, Vasanthakumar GR, Sureshbabu VV (2003) Isocyanates of Na-[(9- Fluorenylmethyl)oxy]carbonyl amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of urea peptidomimetics. J Org Chem 68:7274-7280 (Pubitemid 37122476)
27. Quilico A (ed) (1962) Five and six membered compounds with oxygen and nitrogen. Wiley Interscience, New York, pp 1-46
28. Savant MM, Pansuriya AM, Bhuva CV, Kapuriya N, Patel AS, Audichya VB, Pipaliya PV, Naliapara YT (2010) Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals. J Comb Chem 12:176-180
29. Short KM, Ziegler CB (1993) The synthesis of isoxazoles from b, c-acetylinic oximes. Tetrahedron Lett 34:75-78
30. Shusheng Z, Tianrong Z, Kun C, Youfeng X, Bo Y (2008) Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents. Eur J Med Chem 43:2778-2783
31. Sureshbabu VV, Patil BS, Venkataramanarao R (2006) Preparation, isolation, and characterization of Na-Fmoc-peptide isocyanates: solution synthesis of oligo-a-peptidyl ureas. J Org Chem 71: 7697-7705 (Pubitemid 44470311)
32. Tam A, Arnold U, Soellner MB, Raines RT (2007) Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates. J Am Chem Soc 129:12670-12671 (Pubitemid 350004470)
33. Vig R, Mao C, Venkatachalam TK, Tuel-Ahlgren L, Sudbeck EA, Uckun FM (1998) Rational design and synthesis of phenethyl-5- bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase. Bioorg Med Chem 6: 1789-1797 (Pubitemid 28524233)
34. Wang K, Xiang D, Liu J, Pan W, Dong D (2008) Efficient and divergent synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes. Org Lett 10:1691-1694
35. You S-L, Kelly JW (2005) Total synthesis of didmolamides A and B. Tetrahedron Lett 46:2567-2570 (Pubitemid 40386414)
36. You S-L, Deechongkit S, Kelly JW (2004) Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc a-amino acids. Org Lett 6:2627-2630 (Pubitemid 39077785)
37. Yu K-L, Johnson RL (1987) Synthesis and chemical properties of tetrazole peptide analogs. J Org Chem 52:2051-2059