3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]
Publication type: Journal Article
Publication date: 2017-05-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28481090
Organic Chemistry
Abstract
A new synthetic approach to biologically relevant spiro[pyrrolidine-3,3'-oxindoles] was developed on the basis of the cascade transformation of 3-(2-azidoethyl)oxindoles via Staudinger/aza-Wittig/Mannich reactions. The parent azides were readily synthesized through a nucleophilic ring opening of spiro[cyclopropane-1,3'-oxindoles] with the azide ion. A series of new spiro[pyrrolidine-3,3'-oxindoles] with various (het)aryl substituents at the C2 and C5 positions of the pyrrolidine ring were synthesized. In vitro experiments revealed their high cytotoxicity toward LNCaP and PC-3 tumor cell lines.
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39
Total citations:
39
Citations from 2024:
3
(7%)
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GOST
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Akaev A. A. et al. 3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles] // Journal of Organic Chemistry. 2017. Vol. 82. No. 11. pp. 5689-5701.
GOST all authors (up to 50)
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Akaev A. A., Villemson E. V., Vorobyeva N. S., Majouga A. G., Budynina E. M., Melnikov M. Y. 3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles] // Journal of Organic Chemistry. 2017. Vol. 82. No. 11. pp. 5689-5701.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.7b00529
UR - https://doi.org/10.1021/acs.joc.7b00529
TI - 3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]
T2 - Journal of Organic Chemistry
AU - Akaev, Andrey A
AU - Villemson, Elena V
AU - Vorobyeva, Nataliya S
AU - Majouga, Alexander G.
AU - Budynina, Ekaterina M
AU - Melnikov, Mikhail Y.
PY - 2017
DA - 2017/05/19
PB - American Chemical Society (ACS)
SP - 5689-5701
IS - 11
VL - 82
PMID - 28481090
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Akaev,
author = {Andrey A Akaev and Elena V Villemson and Nataliya S Vorobyeva and Alexander G. Majouga and Ekaterina M Budynina and Mikhail Y. Melnikov},
title = {3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.7b00529},
number = {11},
pages = {5689--5701},
doi = {10.1021/acs.joc.7b00529}
}
Cite this
MLA
Copy
Akaev, Andrey A., et al. “3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles].” Journal of Organic Chemistry, vol. 82, no. 11, May. 2017, pp. 5689-5701. https://doi.org/10.1021/acs.joc.7b00529.
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