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Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton

Iris Wauters (UGent) , Ann De Blieck (UGent) , Koen Muylaert (UGent) , Thomas Heugebaert (UGent) and Christian Stevens (UGent)
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Organization
Abstract
The synthesis of 1-cyano-2-aza-[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were fully deprotected to give the potentially active compounds. The highly hydrophilic character of the compounds resulted in a difficult isolation and purification of the epibatidine analogues.
Keywords
AGONISTS, BINDING, DISCOVERY, IBOGAINE, DIOSCORINE, 2_4-METHANOPROLINE, Nitrogen heterocycles, PAIN, ANALGESICS, Medicinal chemistry, Biological activity, Cyclization, Cyanides, INTRAMOLECULAR SUBSTITUTION SEQUENCE, Natural products, NICOTINIC ACETYLCHOLINE-RECEPTORS

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MLA
Wauters, Iris, Ann De Blieck, Koen Muylaert, et al. “Synthesis of Epibatidine Analogues Having a 2-substituted 2-azabicyclo[2.2.2]octane Skeleton.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2014.6 (2014): 1296–1304. Print.
APA
Wauters, I., De Blieck, A., Muylaert, K., Heugebaert, T., & Stevens, C. (2014). Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(6), 1296–1304.
Chicago author-date
Wauters, Iris, Ann De Blieck, Koen Muylaert, Thomas Heugebaert, and Christian Stevens. 2014. “Synthesis of Epibatidine Analogues Having a 2-substituted 2-azabicyclo[2.2.2]octane Skeleton.” European Journal of Organic Chemistry 2014 (6): 1296–1304.
Chicago author-date (all authors)
Wauters, Iris, Ann De Blieck, Koen Muylaert, Thomas Heugebaert, and Christian Stevens. 2014. “Synthesis of Epibatidine Analogues Having a 2-substituted 2-azabicyclo[2.2.2]octane Skeleton.” European Journal of Organic Chemistry 2014 (6): 1296–1304.
Vancouver
1.
Wauters I, De Blieck A, Muylaert K, Heugebaert T, Stevens C. Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014;2014(6):1296–304.
IEEE
[1]
I. Wauters, A. De Blieck, K. Muylaert, T. Heugebaert, and C. Stevens, “Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 6, pp. 1296–1304, 2014.
@article{4411174,
  abstract     = {The synthesis of 1-cyano-2-aza-[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were fully deprotected to give the potentially active compounds. The highly hydrophilic character of the compounds resulted in a difficult isolation and purification of the epibatidine analogues.},
  author       = {Wauters, Iris and De Blieck, Ann and Muylaert, Koen and Heugebaert, Thomas and Stevens, Christian},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {AGONISTS,BINDING,DISCOVERY,IBOGAINE,DIOSCORINE,2_4-METHANOPROLINE,Nitrogen heterocycles,PAIN,ANALGESICS,Medicinal chemistry,Biological activity,Cyclization,Cyanides,INTRAMOLECULAR SUBSTITUTION SEQUENCE,Natural products,NICOTINIC ACETYLCHOLINE-RECEPTORS},
  language     = {eng},
  number       = {6},
  pages        = {1296--1304},
  title        = {Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton},
  url          = {http://dx.doi.org/10.1002/ejoc.201301397},
  volume       = {2014},
  year         = {2014},
}

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