Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes
Publication type: Journal Article
Publication date: 2002-07-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Two new long-chain acetylene alcohols named lembehynes B ( 2 ) and C ( 3 ) were isolated from an Indonesian marine sponge of Haliclona sp. Lembehynes B ( 2 ) and C ( 3 ), which have different types of long carbon-chain parts compared with that of lembehyne A ( 1 ), also exhibited neuritogenic activity against a neuroblastoma cell line, Neuro 2A. For structure–activity relationship study of lembehynes, analogue-I ( 4 ), analogue-II ( 5 ) and analogue-III ( 6 ), which have different types of long carbon-chain parts, were synthesized from suitable fatty acids. As a result of neurite outgrowth assay for these related compounds, it was revealed that the carbon-chain length is important for neuritogenic activity, while the unsaturated bonds in the long-chain part are not. On the other hand, analogue-IV ( 7 ) with 3 S configuration showed much weaker activity than analogue-III ( 6 ) with 3 R configuration and the same type of long carbon-chain part. This indicates the importance of the stereochemistry of the hydroxyl group at C-3 in lembehynes for neuritogenic activity.
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Total citations:
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Citations from 2024:
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(9.52%)
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GOST
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Aoki S. et al. Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes // Tetrahedron. 2002. Vol. 58. No. 27. pp. 5417-5422.
GOST all authors (up to 50)
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Aoki S., Matsui K., Wei H., Murakami N., Kobayashi M. Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes // Tetrahedron. 2002. Vol. 58. No. 27. pp. 5417-5422.
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RIS
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TY - JOUR
DO - 10.1016/S0040-4020(02)00519-7
UR - https://doi.org/10.1016/S0040-4020(02)00519-7
TI - Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes
T2 - Tetrahedron
AU - Aoki, Shunji
AU - Matsui, Kouhei
AU - Wei, Hong
AU - Murakami, Nobutoshi
AU - Kobayashi, Motomasa
PY - 2002
DA - 2002/07/01
PB - Elsevier
SP - 5417-5422
IS - 27
VL - 58
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2002_Aoki,
author = {Shunji Aoki and Kouhei Matsui and Hong Wei and Nobutoshi Murakami and Motomasa Kobayashi},
title = {Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes},
journal = {Tetrahedron},
year = {2002},
volume = {58},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/S0040-4020(02)00519-7},
number = {27},
pages = {5417--5422},
doi = {10.1016/S0040-4020(02)00519-7}
}
Cite this
MLA
Copy
Aoki, Shunji, et al. “Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes.” Tetrahedron, vol. 58, no. 27, Jul. 2002, pp. 5417-5422. https://doi.org/10.1016/S0040-4020(02)00519-7.