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Volumn 74, Issue 16, 2009, Pages 6072-6076

Stereocontrolled synthesis and pharmacological evaluation of cis-2, 6-diphenethyl-1-azabicyclo[2.2.2]octanes as lobelane analogues

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CHEMICAL REACTIONS;

EID: 70349152205     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901082r     Document Type: Article
Times cited : (5)

References (38)
  • 6
    • 84882530434 scopus 로고    scopus 로고
    • Wermuth, C. G., Ed.; Elsevier/Academic Press: Burlington/San Diego/London, Chapter 17
    • Mann, A. In The Practice of Medicinal Chemistry, 3rd ed.; Wermuth, C. G., Ed.; Elsevier/Academic Press: Burlington/San Diego/London, 2008; Chapter 17, pp 363-379.
    • (2008) The Practice of Medicinal Chemistry, 3rd Ed , pp. 363-379
    • Mann, A.1
  • 9
    • 84924243818 scopus 로고    scopus 로고
    • The reaction was completed in 12 days, reduced to 5 days when the reaction temperature was increased by using propionic anhydride; however, the yield dropped to ca. 25%
    • (a) The reaction was completed in 12 days, reduced to 5 days when the reaction temperature was increased by using propionic anhydride; however, the yield dropped to ca. 25%.
  • 10
    • 84924237566 scopus 로고    scopus 로고
    • The isolation and purification of 9 turned out to be tedious
    • (b) The isolation and purification of 9 turned out to be tedious.
  • 11
    • 84924255203 scopus 로고    scopus 로고
    • note
    • Compound 12 was obtained in only 36% yield even after reflux for 4 days, along with the recovery of 45% of the starting material 11. Similar results were observed when acetone was used as the solvent. When alcohols were used as solvent, only the debenzylation product (i.e., compound 10) could be detected. For example, a quantitative amount of 10 was obtained when 11 was treated with BnBr in 4-methyl-2-pentanol (bp 131-134 °C) under reflux for 4 h.
  • 19
    • 84924244483 scopus 로고    scopus 로고
    • For examples, see: (a) Reference 11b
    • For examples, see: (a) Reference 11b.
  • 30
    • 84924277748 scopus 로고    scopus 로고
    • The stoichiometries of PEMgCl and additives, as listed in Table 1, were adjusted to ensure the completion of the reactions, but were not fully optimized
    • The stoichiometries of PEMgCl and additives, as listed in Table 1, were adjusted to ensure the completion of the reactions, but were not fully optimized.
  • 37
    • 84924280416 scopus 로고    scopus 로고
    • As measured by HPLC, after DIBAL-H reduction to a mixture of hydroxyl compounds (i.e., 25 and 26)
    • As measured by HPLC, after DIBAL-H reduction to a mixture of hydroxyl compounds (i.e., 25 and 26).
  • 38
    • 84924279602 scopus 로고    scopus 로고
    • The stereochemistry at C-4 of 25 and 26 was confirmed by NOESY experiments of their corresponding cyclization products 2 and 3
    • The stereochemistry at C-4 of 25 and 26 was confirmed by NOESY experiments of their corresponding cyclization products 2 and 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.