The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase

Joshua N. Buckler; Ehab S. Taher; Nicolas J. Fraser; Anthony C. Willis; Paul D. Carr; Colin J. Jackson; Martin G. Banwell

doi:10.1021/acs.joc.7b01062

The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase

Joshua N. Buckler
, Ehab S. Taher
, Nicolas J. Fraser
, Anthony C. Willis
, Paul D. Carr
, Colin J. Jackson
, Martin G. Banwell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.

Original language	English
Pages (from-to)	7869-7886
Number of pages	18
Journal	Journal of Organic Chemistry
Volume	82
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.7b01062
Publication status	Published - 4 Aug 2017

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title = "The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase",

abstract = "Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.",

author = "Buckler, \{Joshua N.\} and Taher, \{Ehab S.\} and Fraser, \{Nicolas J.\} and Willis, \{Anthony C.\} and Carr, \{Paul D.\} and Jackson, \{Colin J.\} and Banwell, \{Martin G.\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = aug,

day = "4",

doi = "10.1021/acs.joc.7b01062",

language = "English",

volume = "82",

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T1 - The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase

AU - Buckler, Joshua N.

AU - Taher, Ehab S.

AU - Fraser, Nicolas J.

AU - Willis, Anthony C.

AU - Carr, Paul D.

AU - Jackson, Colin J.

AU - Banwell, Martin G.

PY - 2017/8/4

Y1 - 2017/8/4

N2 - Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.

AB - Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.

UR - https://www.scopus.com/pages/publications/85027075137

U2 - 10.1021/acs.joc.7b01062

DO - 10.1021/acs.joc.7b01062

M3 - Article

SN - 0022-3263

VL - 82

SP - 7869

EP - 7886

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase

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