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Volumn 50, Issue 22, 2011, Pages 5162-5165

Core modification of cytisine: A modular synthesis

Author keywords

acetylcholine receptor; cytisine; heterocycles; pyridone; varenicline

Indexed keywords

ACETYLCHOLINE RECEPTOR; CYTISINE; HETEROCYCLES; PYRIDONES; VARENICLINE;

EID: 79956095918     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100441     Document Type: Article
Times cited : (29)

References (36)
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    • Natural cytisine has also been used extensively within Eastern Europe for smoking cessation.
    • Natural cytisine has also been used extensively within Eastern Europe for smoking cessation., J. F. Etter, Arch. Intern. Med. 2006, 166, 1553-1559.
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    • Ref. [4c]
    • Ref. [4c]
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    • Angew. Chem. Int. Ed. 2006, 45, 2419-2423.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2419-2423
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    • Key step of our earlier method was the intramolecular 1,6-addition of a lactam enolate to a 2-pyridone (22 a → 23 a). This was unsuccessful for 22 b → 23 b and 22 c → 23 c where evidence was obtained for addition of the HMDS anion to the heterocycle.
    • T. Gallagher, I. Derrick, P. M. Durkin, C. A. Haseler, C. Hirschhäuser, P. Magrone, J. Org. Chem. 2010, 75, 3766-3774. Key step of our earlier method was the intramolecular 1,6-addition of a lactam enolate to a 2-pyridone (22 a → 23 a). This was unsuccessful for 22 b → 23 b and 22 c → 23 c where evidence was obtained for addition of the HMDS anion to the heterocycle.
    • (2010) J. Org. Chem. , vol.75 , pp. 3766-3774
    • Gallagher, T.1    Derrick, I.2    Durkin, P.M.3    Haseler, C.A.4    Hirschhäuser, C.5    Magrone, P.6
  • 32
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    • All compounds described here are racemic. The synthesis of (R)- 5 a and nonnatural (+)-cytisine has been reported; see Ref. [14] and also.
    • All compounds described here are racemic. The synthesis of (R)- 5 a and nonnatural (+)-cytisine has been reported; see Ref. [14] and also:, M. H. Kim, Y. Park, B. S. Jeong, H. G. Park, S. S. Jew, Org. Lett. 2010, 12, 2826-2829.
    • (2010) Org. Lett. , vol.12 , pp. 2826-2829
    • Kim, M.H.1    Park, Y.2    Jeong, B.S.3    Park, H.G.4    Jew, S.S.5
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    • A related sequence involving configurationally stable cis-piperidines has been described, see Ref. [8a] and.
    • A related sequence involving configurationally stable cis-piperidines has been described, see Ref. [8a] and, T. Honda, R. Takahashi, H. Namiki, J. Org. Chem. 2005, 70, 499-504.
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    • Honda, T.1    Takahashi, R.2    Namiki, H.3
  • 34
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    • For conditions used see the Supporting Information. Selective thionation of the lactam C=O of 19 using Lawesson's reagent failed (see the Supporting Information).
    • For conditions used see the Supporting Information. Selective thionation of the lactam C=O of 19 using Lawesson's reagent failed (see the Supporting Information).
  • 35
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    • 2O caused degradation
    • 2O caused degradation.
  • 36
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    • 50 of 85 n M (cf. (-)-cytisine 7.7 n M; A. Kennett, S. Wonnacott, C. Hirschhäuser, C. A. Haseler, T. Gallagher, unpublished results). Coe et al. have reported that varenicline is three-fold more potent than cytisine at α4β2 in rat cortex; see Ref. [2a]
    • 50 of 85 n M (cf. (-)-cytisine 7.7 n M; A. Kennett, S. Wonnacott, C. Hirschhäuser, C. A. Haseler, T. Gallagher, unpublished results). Coe et al. have reported that varenicline is three-fold more potent than cytisine at α4β2 in rat cortex; see Ref. [2a].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.