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Volumn 13, Issue 10, 2003, Pages 1795-1799

Discovery of 3-amino-4-chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 4 CHLOROPHENYL; 4 CHLORO 3 ANILINE; ANILINE DERIVATIVE; BENZAMIDINE; BENZENE DERIVATIVE; BLOOD CLOTTING FACTOR 10A INHIBITOR; ISOXAZOLINE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

EID: 0037687741     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00130-6     Document Type: Article
Times cited : (35)

References (32)
  • 8
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    • Thrombosis and Coagulation
    • Bristol, J. A. Ed. Academic Press
    • (a) For reviews and references see: Vacca J. P. Thrombosis and Coagulation. In Annual Reports in Med. Chem., Bristol, J. A. Ed. Academic Press, 1998, 33, pp 81-90.
    • (1998) Annual Reports in Med. Chem. , vol.33 , pp. 81-90
    • Vacca, J.P.1
  • 12
    • 0031771350 scopus 로고    scopus 로고
    • (a) For reviews specifically on nonbenzamidines see: Menear K. Curr. Med. Chem. 5:1998;457
    • (1998) Curr. Med. Chem. , vol.5 , pp. 457
    • Menear, K.1
  • 21
    • 0032567968 scopus 로고    scopus 로고
    • During the course of our investigation, two isoxazoline library syntheses were reported. Solid phase: Cheng J.-F., Mjalli A.M.M. Tetrahedron Lett. 39:1998;939.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 939
    • Cheng, J.-F.1    Mjalli, A.M.M.2
  • 22
    • 0031000561 scopus 로고    scopus 로고
    • During the course of our investigation, two isoxazoline library syntheses were reported. Solid phase: Fluorous phase:
    • Fluorous phase: Studer A., Curran D.P. Tetrahedron. 53:1997;6681.
    • (1997) Tetrahedron , vol.53 , pp. 6681
    • Studer, A.1    Curran, D.P.2
  • 23
    • 85031192339 scopus 로고    scopus 로고
    • Representative procedure: 4-Chloro-3-nitrobenzaldehyde (279 mg, 1.5 mmol) was placed in a 4 mL plastic vial with an internal filter and a drain plug. Ethanol (2.5 mL) was added followed by the addition of an aqueous hydroxylamine hydrochloride solution (0.50 mL, 1.8 mmol, 3.74 M) and an aqueous sodium acetate solution (0.79 mL, 1.2 mmol, 1.52 M). The vial was rotated for 12 h on a Barnstead/Thermolyne Labquake Rotator. The ethanol and water are removed under a stream of nitrogen leaving a solid that was washed once with water and dried under dynamic vacuum to give 4-chloro-3-nitro-benzaldehyde oxime.
  • 24
    • 85031190921 scopus 로고    scopus 로고
    • -1.
  • 26
    • 85031187039 scopus 로고    scopus 로고
    • -1.
  • 28
    • 85031180280 scopus 로고    scopus 로고
    • 18 (5.00 g, 16.4 mmol) was heated to reflux in trifluoroacetic acid (80 mL) for 7 h. The solvent was evaporated and the solid judged to be of sufficient purity for further use.
  • 29
    • 85031183604 scopus 로고    scopus 로고
    • 2O in refluxing ethyl acetate.
  • 32
    • 85031190138 scopus 로고    scopus 로고
    • The 3-amino-4-chlorophenyl P1 moiety was incorporated into an analogous series and the pharmacokinetic profile examined in dog. This compound was found to be highly bioavailable (71%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.