메뉴 건너뛰기




Volumn 50, Issue 13, 2011, Pages 3075-3079

Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor

Author keywords

1,5 Benzodiazepine; Atropisomerism; Chirality; Receptors; Vasopressin

Indexed keywords

1,5-BENZODIAZEPINE; ATROPISOMERISM; ATROPISOMERS; CHEMICAL EQUATIONS; NITROGEN HETEROCYCLES; ORTHO-SUBSTITUTION; RECEPTOR LIGANDS; RECEPTORS; VASOPRESSIN;

EID: 79952666391     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007772     Document Type: Article
Times cited : (52)

References (32)
  • 1
    • 1942532946 scopus 로고    scopus 로고
    • For review articles on axial chirality and atropisomerism, see: a Tetrahedron Symposia-in-Print on Atropisomerism (Ed.: J. Clayden)
    • For review articles on axial chirality and atropisomerism, see: a) J. Clayden, Tetrahedron 2004, 60, 4335 in Tetrahedron Symposia-in-Print on Atropisomerism (Ed.: J. Clayden);
    • (2004) Tetrahedron , vol.60 , pp. 4335
    • Clayden, J.1
  • 3
    • 70349894963 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 6398-6401.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6398-6401
  • 4
    • 0004474923 scopus 로고    scopus 로고
    • For the axial chirality arising from the sp2-sp2 axis of the benzene-amide bond in biologically active compounds, see
    • For the axial chirality arising from the sp2-sp2 axis of the benzene-amide bond in biologically active compounds, see: a) Y. Ikeura, T. Doi, A. Fujishima, H. Natsugari, Chem. Commun. 1998, 2141-2142;
    • (1998) Chem. Commun. , pp. 2141-2142
    • Ikeura, Y.1    Doi, T.2    Fujishima, A.3    Natsugari, H.4
  • 5
    • 15644372975 scopus 로고    scopus 로고
    • see the Supporting Information
    • b) Y. Ikeura et al., J. Med. Chem. 1998, 41, 4232-4239 (see the Supporting Information);
    • (1998) J. Med. Chem. , vol.41 , pp. 4232-4239
    • Ikeura, Y.1
  • 6
    • 0033598446 scopus 로고    scopus 로고
    • see the Supporting Information
    • c) H. Natsugari et al., J. Med. Chem. 1999, 42, 3982-3993 (see the Supporting Information);
    • (1999) J. Med. Chem. , vol.42 , pp. 3982-3993
    • Natsugari, H.1
  • 7
    • 0037194617 scopus 로고    scopus 로고
    • see the Supporting Information
    • d) J. S. Albert et al., J. Med. Chem. 2002, 45, 3972-3983 (see the Supporting Information);
    • (2002) J. Med. Chem. , vol.45 , pp. 3972-3983
    • Albert, J.S.1
  • 9
    • 33846404916 scopus 로고    scopus 로고
    • see the Supporting Information
    • f) S. D. Guile et al., J. Med. Chem. 2007, 50, 254-263 (see the Supporting Information);
    • (2007) J. Med. Chem. , vol.50 , pp. 254-263
    • Guile, S.D.1
  • 11
    • 61349167971 scopus 로고    scopus 로고
    • see the Supporting Information
    • h) J. Porter et al., Bioorg. Med. Chem. Lett. 2009, 19, 1767-1772 (see the Supporting Information).
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1767-1772
    • Porter, J.1
  • 12
    • 9544238082 scopus 로고    scopus 로고
    • see the Supporting Information
    • H. Ogawa et al., J. Med. Chem. 1996, 39, 3547-3555 (see the Supporting Information).
    • (1996) Med. Chem. , vol.39 , pp. 3547-3555
    • Ogawa, H.1
  • 13
    • 77956170241 scopus 로고    scopus 로고
    • For review articles on recent advances in vasopressin receptor ligands, see
    • For review articles on recent advances in vasopressin receptor ligands, see: a) T. Ryckmans, Annu. Rep. Med. Chem. 2009, 44, 129-147;
    • (2009) Annu. Rep. Med. Chem. , vol.44 , pp. 129-147
    • Ryckmans, T.1
  • 15
    • 85069256931 scopus 로고    scopus 로고
    • see the Supporting Information
    • a) J. D. Albright et al., J. Med. Chem. 1998, 41, 2442-2444 (see the Supporting Information);
    • (1998) J. Med. Chem. , vol.41 , pp. 2442-2444
    • Albright, J.D.1
  • 17
    • 0032811742 scopus 로고    scopus 로고
    • see the Supporting Information
    • a) K. Kondo et al., Bioorg. Med. Chem. 1999, 7, 1743-1757 (see the Supporting Information);
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 1743-1757
    • Kondo, K.1
  • 21
    • 79952682685 scopus 로고    scopus 로고
    • The description "cis/trans" is used for the relative arrangement of the two benzene rings
    • The description "cis/trans" is used for the relative arrangement of the two benzene rings.
  • 22
    • 79952645272 scopus 로고    scopus 로고
    • note
    • Herein, for convenience, the description of the axial chirality (aS and aR) is used so that the substituent R is lower in priority than the seven-membered ring chain [formally, the definition is reversed in the case of 3 (A and B; R=Cl)]. The terms aS and aR (chiral axis nomenclature) correspond to P and M (helix nomenclature), respectively.
  • 23
    • 79952688681 scopus 로고    scopus 로고
    • For the preparation of the parent 1,5-benzodiazepines (7a-c, 8), see the Supporting Information
    • For the preparation of the parent 1,5-benzodiazepines (7a-c, 8), see the Supporting Information.
  • 24
    • 79952675118 scopus 로고    scopus 로고
    • note
    • 3 group in the major cis isomer showed a correlation with the protons of the benzoyl ring (see the Supporting Information).
  • 25
    • 79952640172 scopus 로고    scopus 로고
    • note
    • Kα radiation was used for the measurement).
  • 28
    • 79952659326 scopus 로고    scopus 로고
    • For determination of the ΔG≠ value, see the Supporting Information
    • For determination of the ΔG≠ value, see the Supporting Information.
  • 29
    • 79952680093 scopus 로고    scopus 로고
    • note
    • [16]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.