Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase

Christopher J. Douglas; Heather M. Sklenicka; Hong C. Shen; David S. Mathias; Shane J. Degen; Geoffrey M. Golding; Christopher D. Morgan; Regina A. Shih; Kristen L. Mueller; Lisa M. Seurer; Erik W. Johnson; Richard P. Hsung

doi:10.1016/S0040-4020(99)00847-9

Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase

Christopher J. Douglas, Heather M. Sklenicka, Hong C. Shen, David S. Mathias, Shane J. Degen, Geoffrey M. Golding, Christopher D. Morgan, Regina A. Shih, Kristen L. Mueller, Lisa M. Seurer, Erik W. Johnson, Richard P. Hsung

Chemistry (Twin Cities)

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

60 Scopus citations

Abstract

4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.

Original language	English (US)
Pages (from-to)	13683-13696
Number of pages	14
Journal	Tetrahedron
Volume	55
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4020(99)00847-9
State	Published - Nov 26 1999

Keywords

Electronic Effects
Electronic Spectra
NMR
Pyrones

Publisher link

10.1016/S0040-4020(99)00847-9

Find It

Find It at U of M Libraries

Cite this

Douglas, C. J., Sklenicka, H. M., Shen, H. C., Mathias, D. S., Degen, S. J., Golding, G. M., Morgan, C. D., Shih, R. A., Mueller, K. L., Seurer, L. M., Johnson, E. W., & Hsung, R. P. (1999). Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase. Tetrahedron, 55(48), 13683-13696. https://doi.org/10.1016/S0040-4020(99)00847-9

Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase. / Douglas, Christopher J.; Sklenicka, Heather M.; Shen, Hong C. et al.
In: Tetrahedron, Vol. 55, No. 48, 26.11.1999, p. 13683-13696.

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

Douglas, CJ, Sklenicka, HM, Shen, HC, Mathias, DS, Degen, SJ, Golding, GM, Morgan, CD, Shih, RA, Mueller, KL, Seurer, LM, Johnson, EW & Hsung, RP 1999, 'Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase', Tetrahedron, vol. 55, no. 48, pp. 13683-13696. https://doi.org/10.1016/S0040-4020(99)00847-9

@article{2dc9ac7232e74899b5b2d56ae9cebb8b,

title = "Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase",

abstract = "4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.",

keywords = "Electronic Effects, Electronic Spectra, NMR, Pyrones",

author = "Douglas, {Christopher J.} and Sklenicka, {Heather M.} and Shen, {Hong C.} and Mathias, {David S.} and Degen, {Shane J.} and Golding, {Geoffrey M.} and Morgan, {Christopher D.} and Shih, {Regina A.} and Mueller, {Kristen L.} and Seurer, {Lisa M.} and Johnson, {Erik W.} and Hsung, {Richard P.}",

year = "1999",

month = nov,

day = "26",

doi = "10.1016/S0040-4020(99)00847-9",

language = "English (US)",

volume = "55",

pages = "13683--13696",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "48",

}

TY - JOUR

T1 - Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase

AU - Douglas, Christopher J.

AU - Sklenicka, Heather M.

AU - Shen, Hong C.

AU - Mathias, David S.

AU - Degen, Shane J.

AU - Golding, Geoffrey M.

AU - Morgan, Christopher D.

AU - Shih, Regina A.

AU - Mueller, Kristen L.

AU - Seurer, Lisa M.

AU - Johnson, Erik W.

AU - Hsung, Richard P.

PY - 1999/11/26

Y1 - 1999/11/26

N2 - 4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.

AB - 4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.

KW - Electronic Effects

KW - Electronic Spectra

KW - NMR

KW - Pyrones

UR - http://www.scopus.com/inward/record.url?scp=0033607796&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033607796&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00847-9

DO - 10.1016/S0040-4020(99)00847-9

M3 - Article

AN - SCOPUS:0033607796

SN - 0040-4020

VL - 55

SP - 13683

EP - 13696

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase

Abstract

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this