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Volumn 3, Issue 6, 2001, Pages 865-868

3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: Synthesis of a conformationally restricted inhibitor of farnesyltransferase

Author keywords

[No Author keywords available]

Indexed keywords

3,8 DIAZABICYCLO(3.2.1)OCTAN 2 ONE; 3,8-DIAZABICYCLO(3.2.1)OCTAN-2-ONE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENZYME INHIBITOR; FARNESYL TRANS TRANSFERASE; FUSED HETEROCYCLIC RINGS; PEPTIDE; TRANSFERASE;

EID: 0035932606     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015504w     Document Type: Article
Times cited : (30)

References (44)
  • 24
    • 0042121974 scopus 로고    scopus 로고
    • note
    • 3N, DMF), and HPLC analysis to confirm ≥ 97% enantiomer purity.
  • 25
    • 0042623053 scopus 로고    scopus 로고
    • note
    • Transannular alkylation of the methanesulfonate i under the same conditions provided an 8:1 mixture of 9a and the alcohol derived from cleavage of the methanesulfonyl group. Attempts to cyclize the sulfonium salt ii derived from L-methionine were unsuccessful. matrix presented
  • 27
    • 0042121975 scopus 로고    scopus 로고
    • note
    • Attempted cyclization using LiHMDS (THF, -78 to 0°C, 5 h) gave only recovered 11. The use of KHMDS under the same conditions resulted in gradual conversion to the dihydrooxazinone iii. matrix presented
  • 34
    • 0042623052 scopus 로고    scopus 로고
    • manuscript in preparation
    • (b) manuscript in preparation.
  • 40
    • 0041621099 scopus 로고    scopus 로고
    • note
    • (a) Molecular modeling: Conformations were generated using metric matrix distance geometry algorithm JG (S. Kearsley, Merck & Co., Inc., unpublished). The structures were subjected to energy minimization within Macromodel (ref 20b) using the MMFF force field.
  • 42
    • 0041621101 scopus 로고    scopus 로고
    • note
    • This interpretation is supported by computational analyses (ref 20), which revealed only moderate energy increases for the following conformational perturbations relative to lowest energy 19 (cf. Figure 2): front-to-back rotations of the imidazole, cyanophenyl rings and back-to-front rotation of the chlorophenyl ring (1.66 kcal/mol); axial - equatorial isomerization (2.94 kcal/mol).
  • 43
    • 0041621100 scopus 로고    scopus 로고
    • note
    • An alternative conformation of 13 with the carbonyl projected in the opposite direction relative to 19 is the enantiomer of lowest energy 13.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.