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Volumn 7, Issue 21, 1997, Pages 2735-2740

Design and synthesis of novel 2,7-dialkyl substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamides as in vitro potent peptidomimetic inhibitors of human renin

Author keywords

[No Author keywords available]

Indexed keywords

5(S) AMINO 4(S) HYDROXY 8 PHENYL OCTANECARBOXAMIDE DERIVATIVE; RENIN; RENIN INHIBITOR; UNCLASSIFIED DRUG;

EID: 0141608479     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10067-1     Document Type: Article
Times cited : (42)

References (33)
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    • van der Goot, H.; Dománi, G.; Pallos, L.; Timmerman, H., Eds.; Elsevier Science Publishers: Amsterdam
    • Cohen, N.C. Trends in Med. Chem. '88; van der Goot, H.; Dománi, G.; Pallos, L.; Timmerman, H., Eds.; Elsevier Science Publishers: Amsterdam, 1989; pp. 13-28.
    • (1989) Trends in Med. Chem. '88 , pp. 13-28
    • Cohen, N.C.1
  • 16
    • 0342834977 scopus 로고    scopus 로고
    • note
    • 1 site than the corresponding C7(R)-stereoisomer, in agreement with the in vitro binding data for the ethyl homologues 12, 13.
  • 17
    • 0027934039 scopus 로고
    • An alternative synthesis of the prototype 8-phenyI-2(R),7(R)-dimethyl model analogue of 10 and 11 has been recently disclosed: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1697
    • Hanessian, S.1    Raghavan, S.2
  • 18
    • 0343705428 scopus 로고    scopus 로고
    • note
    • All new compounds have been characterized at least by high resolution 1 H-NMR and/or FAB mass spectrometry.
  • 21
    • 0342834974 scopus 로고    scopus 로고
    • note
    • The precursors of 8a-f were prepared similarly as 5b,c from the mono-substituted benzylbromides and the corresponding (R)configured N-acyl Evans auxiliaries. (S)-8c was prepared from 3-isovaleroyl-4(S)-benzyl-oxazolidin-2-one ((S)-27c).
  • 23
    • 0000925727 scopus 로고
    • Racemisation during cleavage of the oxazolidinone auxiliary by transesterification using the more basic lithium benzyl oxide has been described previously: Trimble, L.A.; Vederas, J.C. J. Am. Chem. Soc. 1986, 108, 6397.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6397
    • Trimble, L.A.1    Vederas, J.C.2
  • 26
    • 0343705427 scopus 로고
    • In our hands, n-butylacrylamide proved to be more stable than methyacrylamide on storage at lower temperature, probably due to a reduced susceptibility for polymerisation (cf. Fitt, J.; Gschwend, H.W. J. Org. Chem. 1980, 45, 4257). The compound could be kept for several months at < -10 °C without signs of decomposition.
    • (1980) J. Org. Chem. , vol.45 , pp. 4257
    • Fitt, J.1    Gschwend, H.W.2
  • 27
    • 0342400254 scopus 로고    scopus 로고
    • note
    • 6) for the 4(S)-vs. 4(R)-isomers. In all cases, the 4(R)-diastereomers corresponding to 7c appeared to be more polar by t.l.c..
  • 28
    • 33845281684 scopus 로고
    • 3 [see: Takaya, H.; Noyori, R. et al, J. Am. Chem. Soc. 1987, 109, 1596] to give the desired 2(R)-methyl isomers (H. Rüeger, personal communication).
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1596
    • Takaya, H.1    Noyori, R.2
  • 29
    • 0343269824 scopus 로고    scopus 로고
    • note
    • The regioisomeric inhibitor 22 was obtained accordingly starting from 4-(tert-butyl)-2-hydroxy-benzoic acid.
  • 33
    • 0342400252 scopus 로고    scopus 로고
    • note
    • 3 extended dipeptide isosteres in our laboratories [Ref. 5].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.