Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity
Publication type: Journal Article
Publication date: 2016-11-07
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient eight-step semisynthetic approach towards nonracemic pyrrolo-allocolchicinoids starting from natural colchicine was developed by exploiting Pd-catalyzed domino Sonogashira coupling/5-endo-dig cyclization of a 2-iodo-trifluoroacetanilide intermediate to build up the heterocyclic ring system. The N-Me substitution of the pyrrole ring enhanced the antitumor activity of the prepared molecules by 2–3 orders of magnitude. Among the active compounds, the N-methylated colchicinoid exhibited powerful cytotoxic and antiproliferative properties at concentrations < 1 nm.
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17
Total citations:
17
Citations from 2024:
1
(5.88%)
Cite this
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MLA
Cite this
GOST
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Shchegravina E. S. et al. Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 34. pp. 5620-5623.
GOST all authors (up to 50)
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Shchegravina E. S., Knyazev D. I., Beletskaya I. P., Svirshchevskaya E. V., Schmalz H. Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 34. pp. 5620-5623.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/ejoc.201601069
UR - https://doi.org/10.1002/ejoc.201601069
TI - Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity
T2 - European Journal of Organic Chemistry
AU - Shchegravina, Ekaterina S.
AU - Knyazev, Dmitry I
AU - Beletskaya, Irina P.
AU - Svirshchevskaya, E. V.
AU - Schmalz, H.-G.
PY - 2016
DA - 2016/11/07
PB - Wiley
SP - 5620-5623
IS - 34
VL - 2016
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Shchegravina,
author = {Ekaterina S. Shchegravina and Dmitry I Knyazev and Irina P. Beletskaya and E. V. Svirshchevskaya and H.-G. Schmalz},
title = {Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity},
journal = {European Journal of Organic Chemistry},
year = {2016},
volume = {2016},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.201601069},
number = {34},
pages = {5620--5623},
doi = {10.1002/ejoc.201601069}
}
Cite this
MLA
Copy
Shchegravina, Ekaterina S., et al. “Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity.” European Journal of Organic Chemistry, vol. 2016, no. 34, Nov. 2016, pp. 5620-5623. https://doi.org/10.1002/ejoc.201601069.
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