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Bioorganic and Medicinal Chemistry Letters
Volumn 3, Issue 6, 1993, Pages 1055-1060
N1-sterically hindered 2H-imidazol-2-one angiotensin II receptor antagonists: The conversion of surmountable antagonists to insurmountable antagonists
Author keywords

[No Author keywords available]
Indexed keywords

4 BUTYL 1 (2 METHYLPHENYL) 3 [6 [2 (5 TETRAZOLYL)PHENYL] 3 PYRIDYLMETHYL] 2 IMIDAZOLONE; 4 BUTYL 1 (2,6 DIMETHYLPHENYL) 3 [6 [2 (5 TETRAZOLYL)PHENYL] 3 PYRIDYLMETHYL] 2 IMIDAZOLONE; ANGIOTENSIN II ANTAGONIST; ANGIOTENSIN RECEPTOR; IMIDAZOLE DERIVATIVE; SC 54628; SC 54629; UNCLASSIFIED DRUG;
EID: 0027205054     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)80286-3     Document Type: Article
Times cited : (21)
References (14)
  • 2
    • 84913184484 scopus 로고    scopus 로고
    • Reitz, D. B.; Manning, R. E. U.S. Patent 5,087,634 (2/11/92); Eur. Patent Appl. WO 92/07834 (5/14/92).
  • 4
    • 84913184483 scopus 로고    scopus 로고
    • Reitz, D.B. U.S. Patent 5,098,920 (3/24/92); Eur. Patent Appl. WO 91/17148 (11/14/91).
  • 5
    • 84913184482 scopus 로고    scopus 로고
    • Reitz, D. B.; Manning, R.E. U.S. Patent 5,164,403 (11/17/92); Eur. Patent Appl. WO 92/17469 (10/15/92).
  • 6
    • 84913184481 scopus 로고    scopus 로고
    • Reitz, D.B. U.S. Patent 5,155,117 (10/13/92); Eur. Patent Appl. WO 92/18092 (10/29/92).
  • 8
    • 84913184480 scopus 로고    scopus 로고
    • Molecular mechanics calulations were done using MacroModel MM2, Version 2.5.
  • 9
    • 84913184479 scopus 로고    scopus 로고
    • In ethyl benzene, the low energy conformation has the ethyl group perpendicular to the phenyl ring (c-c-C-C torsional angle= 90°;, c= aromatic carbon, C= aliphatic carbon). In isopropyl benzene, the phenyl ring bisects the C-C-C angle of the isopropyl side chain (c-c-C-C angle= 120°; c-c-C-H angle equals 0°). In the 2-isopropylphenyl-2H-imidazol-2-one analog, the terminal methyl groups of the isopropyl side chain are orientated away from the 2H-imidazol-2-one ring and the methine hydrogen atom is pointed towards the 2H-imidazol-2-one ring system. From the point of view of the 2H-imidazol-2-one ring, the 2-isopropyl-phenyl group is effectively smaller than the 2-ethylphenyl group due to its orientation in its low energy conformation.
  • 13
    • 84913184478 scopus 로고    scopus 로고
    • All new compounds were fully characterized spectrally; purity was established by a combination of analytical HPLC and HRMS and/or combustion analysis. Complete synthetic procedures with thorough AII analog characterization will be published elsewhere.

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