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Volumn 18, Issue 20, 2008, Pages 5448-5450

Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis

Author keywords

Abeo sterols; Cytotoxicity; Mycobacterium tuberculosis; Synthesis; Tuberculosis

Indexed keywords

CHOLESTANE DERIVATIVE; CYCLOPENTANE; RIFAMPICIN; STEROL DERIVATIVE; TUBERCULOSTATIC AGENT;

EID: 53649108932     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.09.029     Document Type: Article
Times cited : (25)

References (23)
  • 1
    • 28844508736 scopus 로고    scopus 로고
    • Tuberculosis
    • Kasper D.L., Braunwald E., Fauci A.S., Hauser S.L., Longo D.L., Jameson J.L., and Isselbacher K.J. (Eds), McGraw-Hill Professional
    • Raviglione M.C., and O'Brien R.J. Tuberculosis. In: Kasper D.L., Braunwald E., Fauci A.S., Hauser S.L., Longo D.L., Jameson J.L., and Isselbacher K.J. (Eds). Harrison's Principles of Internal Medicine (2004), McGraw-Hill Professional 953
    • (2004) Harrison's Principles of Internal Medicine , pp. 953
    • Raviglione, M.C.1    O'Brien, R.J.2
  • 2
    • 53649111370 scopus 로고    scopus 로고
    • World Health Organization (WHO). Tuberculosis Fact sheet No. 104-Global and Regional Incidence, March 2006.
    • World Health Organization (WHO). Tuberculosis Fact sheet No. 104-Global and Regional Incidence, March 2006.
  • 4
    • 33645119729 scopus 로고    scopus 로고
    • Emergence of Mycobacterium tuberculosis with extensive resistance to second-line drugs-worldwide, 2000-2004. MMWR Morb. Mortal Wkly. Rep. 2006, 55, 301.
    • Emergence of Mycobacterium tuberculosis with extensive resistance to second-line drugs-worldwide, 2000-2004. MMWR Morb. Mortal Wkly. Rep. 2006, 55, 301.
  • 6
    • 0032757229 scopus 로고    scopus 로고
    • Steroids are important natural products that possess diverse biological activity, including cytotoxic and antimycobacterial activities. For recent articles related to the antitubercular properties of naturally occurring steroids, see:
    • Steroids are important natural products that possess diverse biological activity, including cytotoxic and antimycobacterial activities. For recent articles related to the antitubercular properties of naturally occurring steroids, see:. Cantrell C.L., Rajab M.S., Franzblau S.G., Fronczek F.R., and Fischer N.H. Planta Med. 65 (1999) 732
    • (1999) Planta Med. , vol.65 , pp. 732
    • Cantrell, C.L.1    Rajab, M.S.2    Franzblau, S.G.3    Fronczek, F.R.4    Fischer, N.H.5
  • 14
    • 53649087017 scopus 로고    scopus 로고
    • note
    • The starting sterols 24-methylene-cholesterol (1) and 24-α-ethyl-cholesterol (4) were extracted, respectively, from the Caribbean marine sponges S. zeai and Myrmekioderma styx. Commercial cholesterol (6) was purchased from Aldrich Chemical Company. Gorgosterol (8) and 24-α-methyl-cholesterol (10) were extracted from the Caribbean gorgonian octocoral Gorgonia mariae. Abeo-sterol 3 was prepared from precursor 1 as described.
  • 15
    • 53649109028 scopus 로고    scopus 로고
    • note
    • 4), and concentrated in vacuo. Purification by silica gel flash column chromatography (hexane/EtOAc 90:10 or hexane/acetone 90:10) afforded the desired 5(6 → 7)abeo-sterol derivatives (15.5-26.0 mg; 30-50% isolated yield) as colorless oils with 97-98% purity.
  • 18
    • 53649100766 scopus 로고    scopus 로고
    • note
    • 2)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.