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Volumn 7, Issue 10, 1997, Pages 1255-1260

Discovery of a novel class of BK channel openers: Enantiospecific synthesis and BK channel opening activity of 3-(5-chloro-2-hydroxyphenyl)-1,3-dihydro-3- hydroxy-6-(trifluoromethyl)-2H-indol-2-one

Author keywords

[No Author keywords available]

Indexed keywords

1 (5 CHLORO 2 HYDROXYPHENYL) 5 TRIFLUOROMETHYL 2 BENZIMIDAZOLONE; INDOLE DERIVATIVE; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT;

EID: 0031579961     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00202-3     Document Type: Article
Times cited : (78)

References (27)
  • 1
    • 0011255114 scopus 로고    scopus 로고
    • Department of Chemistry
    • Department of Chemistry.
  • 2
    • 0011215772 scopus 로고    scopus 로고
    • Department of Central Nervous System Drug Discovery
    • Department of Central Nervous System Drug Discovery.
  • 22
    • 0011240462 scopus 로고    scopus 로고
    • It was found that the enolate of 6 is quite sensitive to even trace amounts of dissolved oxygen and readily undergoes autooxidation, which results in signicficantly reduced asymmetric induction. In order to prevent hydroxylation by molecular oxygen, asymmetric hydroxylation of indolone 6 with the oxaziridines 7 was performed in degassed dry THF under an argon atmosphere
    • It was found that the enolate of 6 is quite sensitive to even trace amounts of dissolved oxygen and readily undergoes autooxidation, which results in signicficantly reduced asymmetric induction. In order to prevent hydroxylation by molecular oxygen, asymmetric hydroxylation of indolone 6 with the oxaziridines 7 was performed in degassed dry THF under an argon atmosphere.
  • 23
    • 0011229834 scopus 로고    scopus 로고
    • Previously, chiral shift reagents have been used to determine the enantiomeric excess of chiral alcohols as described in 21. However, for this series of chiral alcohols, we have found that the use of the chiral solvent (L)-trifluoromethylphenyl carbinol can be used in place of chiral shift reagents to effectively determine the enantiomeric excess of 4c and 4e
    • Previously, chiral shift reagents have been used to determine the enantiomeric excess of chiral alcohols as described in . However, for this series of chiral alcohols, we have found that the use of the chiral solvent (L)-trifluoromethylphenyl carbinol can be used in place of chiral shift reagents to effectively determine the enantiomeric excess of 4c and 4e.
  • 24
    • 0011176856 scopus 로고    scopus 로고
    • In order to establish the absolute stereochemistry of the asymmetric hydroxylation protocol, the absolute configuration of a chiral 5-bromo-3-hydroxyindolone analogue was determined by single crystal X-ray analysis. Thus, oxidation of the potassium enolate of 5-bromo-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one with (1S)-(+)-(10-camphorsulfonyl)oxaziridine afforded (3R)-(-)-5-bromo-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-hydroxy-2H-indol-2-one
    • In order to establish the absolute stereochemistry of the asymmetric hydroxylation protocol, the absolute configuration of a chiral 5-bromo-3-hydroxyindolone analogue was determined by single crystal X-ray analysis. Thus, oxidation of the potassium enolate of 5-bromo-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one with (1S)-(+)-(10-camphorsulfonyl)oxaziridine afforded (3R)-(-)-5-bromo-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-hydroxy-2H-indol-2-one.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.