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Volumn 67, Issue 25, 2002, Pages 8962-8969

The synthesis of azapeptidomimetic β-lactam molecules as potential protease inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

STRUCTURE (COMPOSITION); SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 0037073813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026280d     Document Type: Article
Times cited : (33)

References (74)
  • 1
    • 0031189711 scopus 로고    scopus 로고
    • For reviews on peptidomimetic enzyme inhibitors, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735. (d) Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
    • (1997) Chem. Rev. , vol.97 , pp. 1359
    • Babine, R.E.1    Bender, S.L.2
  • 2
    • 0034628448 scopus 로고    scopus 로고
    • For reviews on peptidomimetic enzyme inhibitors, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735. (d) Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
    • (2000) J. Med. Chem. , vol.43 , pp. 305
    • Leung, D.1    Abbenante, G.2    Fairlie, D.P.3
  • 3
    • 0001651169 scopus 로고    scopus 로고
    • For reviews on peptidomimetic enzyme inhibitors, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735. (d) Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
    • (1999) Chem. Rev. , vol.99 , pp. 2735
    • Whittaker, M.1    Floyd, C.D.2    Brown, P.3    Gearing, A.J.H.4
  • 4
    • 0343433408 scopus 로고    scopus 로고
    • For reviews on peptidomimetic enzyme inhibitors, see: (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359. (b) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305. (c) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735. (d) Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
    • (1997) Chem. Rev. , vol.97 , pp. 133
    • Otto, H.-H.1    Schirmeister, T.2
  • 45
    • 0001807533 scopus 로고
    • a value is due to the polar effect of the α-nitrogen and is significant enough that the dialkylhydrazinodicarboxylate anion can deprotonate the amide nitrogen creating a strong nucleophile. Miller and co-workers have elegantly illustrated and exploited this fact with related acyl hydroxamate compounds. See: Miller, M. J. Acc. Chem. Res. 1986, 19, 49.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 49
    • Miller, M.J.1
  • 59
    • 2242432810 scopus 로고    scopus 로고
    • Monosubstituted Hydrazines. Swiss Patent 307,629, Aug. 16, 1955
    • Giegy, J. R. Monosubstituted Hydrazines. Swiss Patent 307,629, Aug. 16, 1955; Chem. Abstr. 1957, 51, 3113f.
    • Giegy, J.R.1
  • 60
    • 26744463598 scopus 로고
    • Giegy, J. R. Monosubstituted Hydrazines. Swiss Patent 307,629, Aug. 16, 1955; Chem. Abstr. 1957, 51, 3113f.
    • (1957) Chem. Abstr. , vol.51
  • 63
    • 2242436448 scopus 로고    scopus 로고
    • note
    • Abbreviations: EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; BOP, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate.
  • 66
    • 0000379927 scopus 로고
    • The two-step procedure has been used as an alternative to Mitsunobu conditions for serine hydroxamate cyclization to a β-lactam. See: Floyd, D. M.; Fritz, A. W.; Cimarusti, C. M. J. Org. Chem. 1982, 47, 176.
    • (1982) J. Org. Chem. , vol.47 , pp. 176
    • Floyd, D.M.1    Fritz, A.W.2    Cimarusti, C.M.3
  • 67
    • 0019205018 scopus 로고
    • Based on literature precedent with the Mitsunobu reaction of acyl hydroxamates (see: Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026), the β-carbon of L-threonine should undergo inversion of configuration. However, the stereochemistry at C-4 of the azetidinone in 21 could not be determined due to spectral broadening from rotamers.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7026
    • Miller, M.J.1    Mattingly, P.G.2    Morrison, M.A.3    Kerwin J.F., Jr.4
  • 71
    • 2242491098 scopus 로고    scopus 로고
    • note
    • Coupling reagent abbreviations: EEDQ, 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline; HOBt, 1-hydroxybenzotriazole hydrate; PyBOP, benzotriazol-1-yl-N-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; HATU, N-[(dimethylamino)-1H-1,2,3- triazolo[4,5-b]-pyridino-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; i-BCF, isobutylchloroformate.


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