Synthesis of UB-165: A novel nicotinic ligand and anatoxin- a/epibatidine hybrid

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 22, 1997, Pages 2867-2870

  Wright, Emma ^a   Gallagher, Timothy ^a   Sharples, Christopher G V ^b   Wonnacott, Susan ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF BATH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANATOXIN A; EPIBATIDINE; NICOTINIC RECEPTOR;

ARTICLE; BINDING SITE; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0030670102     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10090-7     Document Type: Article

References (24)

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21. 2 +H requires 235.1002 (1.8 ppm).
22. 50 values were determined from the curves, with values shown in Table 1 being the mean ± sem of three independent assays and (±)-(5), UB-165 (5) and ent-(5) were all used as the corresponding HCl salts.
23. pyridine distance against torsion angle was determined with an energy minimised structure using Discover 2.95 (cvff) from MSI/Biosym.
24. Very recently, a tropane variant of epibatidine (derived from (-)-cocaine) has been reported which also uses a Pd(0)-mediated coupling of an organozinc nucleophile (as in Scheme 1) to a tropane-based vinyl inflate: Zhang, C.; Gyermek, L.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 5619.