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Volumn 13, Issue 7, 2003, Pages 1237-1239

A new synthesis of cytoxazone and its diastereomers provides key initial SAR information

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; CYTOXAZONE; UNCLASSIFIED DRUG;

EID: 0037424709     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00131-8     Document Type: Article
Times cited : (38)

References (23)
  • 4
    • 0034480581 scopus 로고    scopus 로고
    • (a) For reviews of the subject, see: Stirling R.G., Chung K.F. Eur. Respir. J. 16:2000;1158. (b) Renauld J.C. J. Clin. Pathol. 54:2001;577.
    • (2000) Eur. Respir. J. , vol.16 , pp. 1158
    • Stirling, R.G.1    Chung, K.F.2
  • 5
    • 0034881918 scopus 로고    scopus 로고
    • (a) For reviews of the subject, see: Stirling R.G., Chung K.F. Eur. Respir. J. 16:2000;1158 (b) Renauld J.C. J. Clin. Pathol. 54:2001;577.
    • (2001) J. Clin. Pathol. , vol.54 , pp. 577
    • Renauld, J.C.1
  • 6
    • 0032540412 scopus 로고    scopus 로고
    • Takacs has described a conceptually identical approach as a generalized synthesis of 4-substituted oxazolidin-2-ones. See: Takacs J.M., Jaber M.R., Vellekoop A.S. J. Org. Chem. 63:1998;2742.
    • (1998) J. Org. Chem. , vol.63 , pp. 2742
    • Takacs, J.M.1    Jaber, M.R.2    Vellekoop, A.S.3
  • 11
    • 85031197344 scopus 로고    scopus 로고
    • note
    • D=-71° for 1 (c=0.1, MeOH, 23°C; see ref 1).
  • 14
    • 85031201601 scopus 로고    scopus 로고
    • note
    • 3H-thymidine (1 mCi/well) and then harvested and counted.
  • 15
    • 85031209997 scopus 로고    scopus 로고
    • note
    • 5 cells/well. Compounds were dissolved in DMSO and serially diluted in media to give a final concentration of 0.3% DMSO. Compounds were added to cells 5 min prior to stimulating the cells with anti-CD3 (R&D Systems) at 1 mg/mL and anti-CD28 (Caltag Laboratories) at 200 μg/mL. Cells were cultured in a final volume of 200 μL at 37°C for 24 h. Supernatants were then harvested and cytokine levels measured by ELISA according to the manufacturer's instructions (Pharmingen).
  • 16
    • 85031203598 scopus 로고    scopus 로고
    • note
    • 4 cells/well in serum free AIM V media (Gibco BRL) in 96-well plates with various concentrations of compound. After incubation for 24 h at 37°C, MTS (Promega) was added to each well at a final concentration of 333 μg/mL. Cell viability was determined after an additional 3 h incubation at 37°C by reading the plates at 490 nM absorbance. Inhibition was determined relative to cells cultured with 1% DMSO.
  • 18
    • 85031196623 scopus 로고    scopus 로고
    • note
    • (b) After the completion of our work, Carda, et al. reported a variation of the aldol/Curtius strategy towards cytoxazone 1 (but not 9) that utilizes an unusual chiral ketone derived in five steps from L-erthrulose.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.