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Volumn 18, Issue 7, 2008, Pages 2316-2319

Deconstructing cytisine: The syntheses of (±)-cyfusine and (±)-cyclopropylcyfusine, fused ring analogs of cytisine

Author keywords

( ) Cyfusine; ( ) Cytisine; ( 3)2 ( 4)3; ( 4)2( 2)3*; 3 + 2 cycloaddition; Cyclopropanation; Cyfusine; Cytisine; nAChR; Nicotinic acetylcholine receptor; Pyridone

Indexed keywords

CYCLOPROPANE DERIVATIVE; CYCLOPROPYLCYFUSINE; CYFUSINE; CYTISINE; EPIBATIDINE; NATURAL PRODUCT; NICOTINE; NICOTINIC AGENT; NICOTINIC RECEPTOR; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VARENICLINE;

EID: 41149113617     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.078     Document Type: Article
Times cited : (18)

References (48)
  • 10
    • 0015209962 scopus 로고    scopus 로고
    • Scharfenberg, G.; Benndorf, S.; Kempe, G. Cytisin (Tabex®) als medikamentöse Raucherentwöhnunshilfe. Dtsch. Gesund-heitsw. 1971, 26, 463.
    • Scharfenberg, G.; Benndorf, S.; Kempe, G. Cytisin (Tabex®) als medikamentöse Raucherentwöhnunshilfe. Dtsch. Gesund-heitsw. 1971, 26, 463.
  • 21
    • 33846543653 scopus 로고    scopus 로고
    • A comprehensive review of the total syntheses of cytisine has recently been published:
    • A comprehensive review of the total syntheses of cytisine has recently been published:. Stead D., and O'Brien P. Tetrahedron 63 (2007) 1885
    • (2007) Tetrahedron , vol.63 , pp. 1885
    • Stead, D.1    O'Brien, P.2
  • 25
    • 41149086486 scopus 로고    scopus 로고
    • O'Neill, B. T. U.S. Patent WO 98/18798, 1998.
    • O'Neill, B. T. U.S. Patent WO 98/18798, 1998.
  • 43
    • 0000277319 scopus 로고
    • The lowest energy conformation of 11 was compared to the crystal structure of 1 (Overall RMS of overlay = 0.61 Å) utilizing Chem3D Ultra (v.10.0), available from CambridgeSoft Inc., 100 CambridgePark Drive, Cambridge, MA 02140 USA. The X-ray structure of (-)-cytisine was retrieved from:
    • The lowest energy conformation of 11 was compared to the crystal structure of 1 (Overall RMS of overlay = 0.61 Å) utilizing Chem3D Ultra (v.10.0), available from CambridgeSoft Inc., 100 CambridgePark Drive, Cambridge, MA 02140 USA. The X-ray structure of (-)-cytisine was retrieved from:. Freer A.A., Robins D.J., and Sheldrake G.N. Acta Cryst. C43 (1987) 1119
    • (1987) Acta Cryst. , vol.C43 , pp. 1119
    • Freer, A.A.1    Robins, D.J.2    Sheldrake, G.N.3
  • 45
    • 41149135913 scopus 로고    scopus 로고
    • note
    • Available from the Aldrich Chemical Company, Cat # 42,069-7.
  • 46
    • 41149161040 scopus 로고    scopus 로고
    • note
    • Compound 7 is oxidatively unstable, converting completely to the pyrrole over several days when exposed to air.
  • 47
    • 41149176732 scopus 로고    scopus 로고
    • note
    • The assays were conducted according to the protocols in the supplementary information in Ref. 11.
  • 48
    • 41149162412 scopus 로고    scopus 로고
    • note
    • 3, 400 MHz) 7.51 (t, 1H), 6.35 (t, 1H), 6.39 (d, J = 8.7 Hz, 1H), 4.23(d, J = 6.6 Hz, 2H), 3.90 to 3.82 (m, 2H), 3.65 to 3.53 (m, 2H), 1.49 (d, J = 5.8 Hz, 1H), 1.45 (s, 9H), 1.32 (d, J = 5.8 Hz, 1H) ppm. Mass spectrum (APCI) m/e 289 p + 1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.