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Volumn 2, Issue 11, 2004, Pages 1633-1642

Design, synthesis and biological activity of a targeted library of potential tryptase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CONFORMATIONS; DIMERIZATION; HYDROGENATION; KETONES; RESINS; SYNTHESIS (CHEMICAL);

EID: 2942735354     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b403629h     Document Type: Article
Times cited : (6)

References (39)
  • 3
    • 2942728769 scopus 로고    scopus 로고
    • Number of reviews on tryptase inhibitors in the last 3 years: 22. Number of patents in the last 3 years: 51
    • Number of reviews on tryptase inhibitors in the last 3 years: 22. Number of patents in the last 3 years: 51.
  • 18
    • 0035955843 scopus 로고    scopus 로고
    • For a review on the syntheses of 3-aminopiperidones in solution, see: (a) C. Flamant-Robin, Q. Wang and N. A. Sasaki, Tetrahedron Lett., 2001, 42, 8483-8484; (b) J. Aubé, Advances in Amino Acid Mimetics and Peptidomimetics, JAY Press Inc, 1997, vol. 1, p. 193.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8483-8484
    • Flamant-Robin, C.1    Wang, Q.2    Sasaki, N.A.3
  • 19
    • 0035955843 scopus 로고    scopus 로고
    • JAY Press Inc
    • For a review on the syntheses of 3-aminopiperidones in solution, see: (a) C. Flamant-Robin, Q. Wang and N. A. Sasaki, Tetrahedron Lett., 2001, 42, 8483-8484; (b) J. Aubé, Advances in Amino Acid Mimetics and Peptidomimetics, JAY Press Inc, 1997, vol. 1, p. 193.
    • (1997) Advances in Amino Acid Mimetics and Peptidomimetics , vol.1 , pp. 193
    • Aubé, J.1
  • 20
    • 2942743495 scopus 로고    scopus 로고
    • The only precedent of a lactamisation on solid phase was reported as a side-reaction in the context of an intramolecular amino acid coupling: Y. Lee and R. B. Silverman, Synthesis, 1999, 495-1499.
    • (1999) Synthesis , pp. 495-1499
    • Lee, Y.1    Silverman, R.B.2
  • 26
    • 45949130729 scopus 로고
    • Alloc-cyclo-Orn was synthesized in solution by cyclodehydration of L-ornithine according to: A. Bladé-Font, Tetrahedron Lett., 1980, 21, 2443-2446 and subsequent protection of the α-amino with an allyloxycarbonyl group following the protocol by E. J. Corey and J. W. Suggs, J. Org. Chem., 1973, 38, 3223-3224. The sample was not optically pure.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 2443-2446
    • Bladé-Font, A.1
  • 27
    • 0000470828 scopus 로고
    • The sample was not optically pure
    • Alloc-cyclo-Orn was synthesized in solution by cyclodehydration of L-ornithine according to: A. Bladé-Font, Tetrahedron Lett., 1980, 21, 2443-2446 and subsequent protection of the α-amino with an allyloxycarbonyl group following the protocol by E. J. Corey and J. W. Suggs, J. Org. Chem., 1973, 38, 3223-3224. The sample was not optically pure.
    • (1973) J. Org. Chem. , vol.38 , pp. 3223-3224
    • Corey, E.J.1    Suggs, J.W.2
  • 28
    • 2942728185 scopus 로고    scopus 로고
    • note
    • Compound 28 was characterised by the NMR and HPLC data of the product cleaved from an aliquot of the resin. The purity determined by HPLC was higher than 95%.
  • 37
    • 2942713515 scopus 로고    scopus 로고
    • note
    • -1.
  • 38
    • 2942758266 scopus 로고    scopus 로고
    • note
    • The manipulation of the resulting dimer was delicate, mainly because of its size and polarity.
  • 39
    • 2942728641 scopus 로고    scopus 로고
    • note
    • We expected to obtain three stereoisomers for compounds 7 prepared from racemic lactams: the racemic RR and SS forms and the meso epimer RS. However, we could not detect the diastereomeric mixture by standard methods such as NMR and analytical HPLC. Since the compounds turned out not to be sufficiently active, we did not pursue this issue.


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