Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors

Naoki Toyooka; Dejun Zhou; Soushi Kobayashi; Hiroshi Tsuneki; Tsutomu Wada; Hideki Sakai; Hideo Nemoto; Toshiyasu Sasaoka; Yasuhiro Tezuka; Subehan; Shigetoshi Kadota; H. Martin Garraffo; Thomas F. Spande; John W. Daly

doi:10.1055/s-2007-1000831

Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors

Naoki Toyooka^*, Dejun Zhou, Soushi Kobayashi, Hiroshi Tsuneki, Tsutomu Wada, Hideki Sakai, Hideo Nemoto, Toshiyasu Sasaoka, Yasuhiro Tezuka, Subehan, Shigetoshi Kadota, H. Martin Garraffo, Thomas F. Spande, John W. Daly

^*Corresponding author for this work

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

11 Scopus citations

Abstract

Syntheses of the structures postulated for 179 and 207E, members of a proposed new class of poison-frog alkaloids, 6,7-dehydro-5,8-disubstituted indolizidines, are described. The FT-IR spectrum and GC retention time of the synthetic 207E were different from those of the natural product; consequently the original structure of 207E needs to be revised. It is likely that the position of the double bond is instead at the 7,8-position.

Original language	English
Pages (from-to)	61-64
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2007-1000831
State	Published - 2008/01/03

Keywords

Dehydro-5,8-disubstituted indolizidines
Inhibitory effects on neuronal nicotinic acetylcholine receptors
Poison-frog alkaloids 179 and 207E

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2007-1000831

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Toyooka, N., Zhou, D., Kobayashi, S., Tsuneki, H., Wada, T., Sakai, H., Nemoto, H., Sasaoka, T., Tezuka, Y., Subehan, Kadota, S., Garraffo, H. M., Spande, T. F., & Daly, J. W. (2008). Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors. Synlett, (1), 61-64. https://doi.org/10.1055/s-2007-1000831

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title = "Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors",

abstract = "Syntheses of the structures postulated for 179 and 207E, members of a proposed new class of poison-frog alkaloids, 6,7-dehydro-5,8-disubstituted indolizidines, are described. The FT-IR spectrum and GC retention time of the synthetic 207E were different from those of the natural product; consequently the original structure of 207E needs to be revised. It is likely that the position of the double bond is instead at the 7,8-position.",

keywords = "Dehydro-5,8-disubstituted indolizidines, Inhibitory effects on neuronal nicotinic acetylcholine receptors, Poison-frog alkaloids 179 and 207E",

author = "Naoki Toyooka and Dejun Zhou and Soushi Kobayashi and Hiroshi Tsuneki and Tsutomu Wada and Hideki Sakai and Hideo Nemoto and Toshiyasu Sasaoka and Yasuhiro Tezuka and Subehan and Shigetoshi Kadota and Garraffo, {H. Martin} and Spande, {Thomas F.} and Daly, {John W.}",

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doi = "10.1055/s-2007-1000831",

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Toyooka, N, Zhou, D, Kobayashi, S, Tsuneki, H , Wada, T , Sakai, H, Nemoto, H, Sasaoka, T, Tezuka, Y, Subehan, Kadota, S, Garraffo, HM, Spande, TF & Daly, JW 2008, 'Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors', Synlett, no. 1, pp. 61-64. https://doi.org/10.1055/s-2007-1000831

TY - JOUR

T1 - Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors

AU - Toyooka, Naoki

AU - Zhou, Dejun

AU - Kobayashi, Soushi

AU - Tsuneki, Hiroshi

AU - Wada, Tsutomu

AU - Sakai, Hideki

AU - Nemoto, Hideo

AU - Sasaoka, Toshiyasu

AU - Tezuka, Yasuhiro

AU - Subehan,

AU - Kadota, Shigetoshi

AU - Garraffo, H. Martin

AU - Spande, Thomas F.

AU - Daly, John W.

PY - 2008/1/3

Y1 - 2008/1/3

N2 - Syntheses of the structures postulated for 179 and 207E, members of a proposed new class of poison-frog alkaloids, 6,7-dehydro-5,8-disubstituted indolizidines, are described. The FT-IR spectrum and GC retention time of the synthetic 207E were different from those of the natural product; consequently the original structure of 207E needs to be revised. It is likely that the position of the double bond is instead at the 7,8-position.

AB - Syntheses of the structures postulated for 179 and 207E, members of a proposed new class of poison-frog alkaloids, 6,7-dehydro-5,8-disubstituted indolizidines, are described. The FT-IR spectrum and GC retention time of the synthetic 207E were different from those of the natural product; consequently the original structure of 207E needs to be revised. It is likely that the position of the double bond is instead at the 7,8-position.

KW - Dehydro-5,8-disubstituted indolizidines

KW - Inhibitory effects on neuronal nicotinic acetylcholine receptors

KW - Poison-frog alkaloids 179 and 207E

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U2 - 10.1055/s-2007-1000831

DO - 10.1055/s-2007-1000831

M3 - 学術論文

AN - SCOPUS:38549131753

SN - 0936-5214

SP - 61

EP - 64

JO - Synlett

JF - Synlett

IS - 1

ER -

Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors

Abstract

Keywords

ASJC Scopus subject areas

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