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Volumn 47, Issue 16, 2006, Pages 2675-2678

Synthesis of novel cyclopropylic sulfones and sulfonamides acting as glucokinase activators

Author keywords

Cyclopropanes; Glucokinase activators; Halogen sulfur exchange; Sulfonamides; Sulfones

Indexed keywords

CYCLOPROPYLIC SULFONE DERIVATIVE; GLUCOKINASE; SULFONAMIDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33644971224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.110     Document Type: Article
Times cited : (11)

References (50)
  • 4
    • 33644970170 scopus 로고    scopus 로고
    • WO 01/44216.
    • WO 01/44216.
  • 6
    • 33644978909 scopus 로고    scopus 로고
    • WO 2004/050645 A1.
    • WO 2004/050645 A1.
  • 10
    • 33644990789 scopus 로고    scopus 로고
    • note
    • SAR results will be published and discussed elsewhere in due course.
  • 41
    • 0028857694 scopus 로고
    • for transformations from thioethers to thiols see also: G.C. Crawley, and M.T. Briggs J. Med. Chem. 38 1995 3951 3956
    • (1995) J. Med. Chem. , vol.38 , pp. 3951-3956
    • Crawley, G.C.1    Briggs, M.T.2
  • 44
    • 33644973370 scopus 로고    scopus 로고
    • note
    • 3, reflux, 22 h (xylene) 78% (two steps)).
  • 45
    • 33644981757 scopus 로고    scopus 로고
    • See Ref. 3a.
    • A similar isomerization of the corresponding methylsulfone has been reported by Corbett et al. In that case, the stronger electron-withdrawing effect of the sulfone as compared to the bromide apparently increased the rate of isomerization such that treatment with methanolic aqueous base at rt for 20 h resulted in complete isomerization without competing saponification. Subsequent removal of methanol and brief heating afforded the E-carboxylic acid exclusively. When these conditions were applied to the bromide, a mixture of E/Z carboxylic acids was obtained. See Ref. 3a.
  • 46
    • 33644978057 scopus 로고    scopus 로고
    • note
    • HPLC was done using a 80 mm ID dynamic axial compression (DAC) Novasep column separating up to 24 g/h of the racemic cyclopropyl alcohol. Conditions: 1 kg Daicel Chiralpak AD (20 μm), mobile phase: 100% MeCN, starting flow rate 150 ml/min, end run flow rate 320 ml/min, 260 nm.
  • 50
    • 33644985174 scopus 로고    scopus 로고
    • note
    • All experimental procedures were similar to those in cited references and any differences are included in stated exp. details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.