Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside
Hayato Fukuda
1
,
Yuko Nishiyama
2
,
Shiina Nakamura
3
,
Yutaro Ohno
3
,
T. Eguchi
4
,
Yoshiharu Iwabuchi
3
,
TAKEO USUI
2
,
Naoki Kanoh
3
1
Publication type: Journal Article
Publication date: 2012-09-27
scimago Q2
wos Q2
SJR: 0.751
CiteScore: 5.9
Impact factor: 3.3
ISSN: 18614728, 1861471X
PubMed ID:
23015368
General Chemistry
Organic Chemistry
Biochemistry
Abstract
We have developed two syntheses of vicenistatin and its analogues. Our first-generation strategy included the rapid and sequential assembly of the macrocyclic lactam by using an intermolecular Horner-Wadsworth-Emmons reaction between the C3-C13 fragment and the C1-C2, C14-C19 fragment, followed by an intramolecular Stille coupling reaction. The second-generation strategy utilized a ring-closing metathesis of a hexaene intermediate to generate the desired 20-membered macrolactam. This second-generation strategy made it possible to prepare synthetic analogues of vicenistatin, including the C20- and/or C23-demethyl analogues. Evaluation of the cytotoxic effect of these analogues indicated the importance of the fixed conformation of aglycon for determining the biological activity of the vicenistatins.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
|
|
|
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
1 publication, 6.67%
|
|
|
Bioorganic and Medicinal Chemistry Letters
1 publication, 6.67%
|
|
|
Tetrahedron
1 publication, 6.67%
|
|
|
Coordination Chemistry Reviews
1 publication, 6.67%
|
|
|
European Journal of Medicinal Chemistry
1 publication, 6.67%
|
|
|
Chemistry - A European Journal
1 publication, 6.67%
|
|
|
European Journal of Organic Chemistry
1 publication, 6.67%
|
|
|
Organic Letters
1 publication, 6.67%
|
|
|
Journal of Organic Chemistry
1 publication, 6.67%
|
|
|
Chemical Communications
1 publication, 6.67%
|
|
|
Natural Product Reports
1 publication, 6.67%
|
|
|
Topics in Heterocyclic Chemistry
1 publication, 6.67%
|
|
|
Synlett
1 publication, 6.67%
|
|
|
Journal of Antibiotics
1 publication, 6.67%
|
|
|
Science advances
1 publication, 6.67%
|
|
|
1
|
Publishers
|
1
2
3
4
|
|
|
Elsevier
4 publications, 26.67%
|
|
|
Wiley
2 publications, 13.33%
|
|
|
American Chemical Society (ACS)
2 publications, 13.33%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 13.33%
|
|
|
Springer Nature
2 publications, 13.33%
|
|
|
The Society of Synthetic Organic Chemistry, Japan
1 publication, 6.67%
|
|
|
Georg Thieme Verlag KG
1 publication, 6.67%
|
|
|
American Association for the Advancement of Science (AAAS)
1 publication, 6.67%
|
|
|
1
2
3
4
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
15
Total citations:
15
Citations from 2024:
2
(13%)
The most citing journal
Citations in journal:
1
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Fukuda H. et al. Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside // Chemistry - An Asian Journal. 2012. Vol. 7. No. 12. pp. 2872-2881.
GOST all authors (up to 50)
Copy
Fukuda H., Nishiyama Y., Nakamura S., Ohno Y., Eguchi T., Iwabuchi Y., USUI T., Kanoh N. Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside // Chemistry - An Asian Journal. 2012. Vol. 7. No. 12. pp. 2872-2881.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/asia.201200615
UR - https://doi.org/10.1002/asia.201200615
TI - Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside
T2 - Chemistry - An Asian Journal
AU - Fukuda, Hayato
AU - Nishiyama, Yuko
AU - Nakamura, Shiina
AU - Ohno, Yutaro
AU - Eguchi, T.
AU - Iwabuchi, Yoshiharu
AU - USUI, TAKEO
AU - Kanoh, Naoki
PY - 2012
DA - 2012/09/27
PB - Wiley
SP - 2872-2881
IS - 12
VL - 7
PMID - 23015368
SN - 1861-4728
SN - 1861-471X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2012_Fukuda,
author = {Hayato Fukuda and Yuko Nishiyama and Shiina Nakamura and Yutaro Ohno and T. Eguchi and Yoshiharu Iwabuchi and TAKEO USUI and Naoki Kanoh},
title = {Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside},
journal = {Chemistry - An Asian Journal},
year = {2012},
volume = {7},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/asia.201200615},
number = {12},
pages = {2872--2881},
doi = {10.1002/asia.201200615}
}
Cite this
MLA
Copy
Fukuda, Hayato, et al. “Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside.” Chemistry - An Asian Journal, vol. 7, no. 12, Sep. 2012, pp. 2872-2881. https://doi.org/10.1002/asia.201200615.