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Volumn 15, Issue 17, 2005, Pages 3912-3916

Estrogen receptor ligands. Part 13: Dihydrobenzoxathiin SERAMs with an optimized antagonist side chain

Author keywords

Estrogen; SERAMs; SERMs

Indexed keywords

ANTIESTROGEN; DIHYDROBENZOXATHIIN; ESTROGEN RECEPTOR ALPHA; LIGAND; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

EID: 23244443558     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.05.089     Document Type: Article
Times cited : (33)

References (36)
  • 22
    • 33544472772 scopus 로고    scopus 로고
    • Aldrich Chemical Company.
    • Aldrich Chemical Company.
  • 23
    • 33544458679 scopus 로고    scopus 로고
    • note
    • 1H NMR. Selected compounds were characterized further by elemental analysis.
  • 24
    • 33544463935 scopus 로고    scopus 로고
    • note
    • Analytical chiral HPLC analysis was performed on a Chiralpak AD 4.6 × 250 mm 10 μm column eluted with 3:1 heptane/isopropanol at 0.4 mL/min. Under these conditions, the major (R,S)-diastereomer of 19 has a retention time of 23.7 min, while the minor (S,S)-diastereomer elutes at 15.1 min.
  • 25
    • 33544460877 scopus 로고    scopus 로고
    • note
    • 1H NMR of the Mosher ester clearly showed the presence of only one diastereomer. By contrast, the corresponding NMR spectrum of the Mosher ester of the 1:1 diastereomeric mixture generated using racemic acid as the starting material clearly showed both diastereomers. Similarly, when the reaction sequence was run with racemic acid and racemic amine as starting materials, the NMR spectrum of the Mosher ester of the product showed ≥3 diastereomers.
  • 26
    • 33544455153 scopus 로고    scopus 로고
    • note
    • 50 values that are reproducible to within a factor of 2-3. Dihydrobenzoxathiin 1 (n = 36) and estradiol (n > 100) were tested in multiple assays; data reported in Table 1 are an average of all determinations.
  • 27
    • 33544456389 scopus 로고    scopus 로고
    • note
    • Data for 7 and 8 reflect a 20 h incubation prior to radioactive quantification; all other data obtained with 3 h incubation.
  • 28
    • 33544465247 scopus 로고    scopus 로고
    • note
    • 9c that measures estrogen agonism and antagonism in rat uterine tissue. Compounds are dosed orally at the indicated doses, except for fulvestrant, which was dosed subcutaneously. Agonism is reported as percentage of estradiol control; antagonism reported as percentage antagonism of estradiol.
  • 29
    • 33544468964 scopus 로고    scopus 로고
    • note
    • Estradiol exhibited 100% agonism at 4 μg/kg.
  • 31
    • 33544471061 scopus 로고    scopus 로고
    • note
    • 50 for the test compound is determined.
  • 34
    • 33544458898 scopus 로고    scopus 로고
    • manuscript in preparation.
    • Hayes, E. C. et al., manuscript in preparation.
    • Hayes, E.C.1
  • 36
    • 33544456541 scopus 로고    scopus 로고
    • manuscript in preparation.
    • Warrier, S. et al., manuscript in preparation.
    • Warrier, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.