The Richter reaction in the synthesis of combretastatin analogs
Publication type: Journal Article
Publication date: 2023-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
The regioselectivity of the Richter cyclization for a series of 4-halo-2-[(3,4,5 trimethoxyphenyl)ethynyl]anilines has been studied to obtain trimethoxybenzoyl-1H-indazoles, heteroanalogs of combretastatin. In aqueous acetonitrile, cinnolin-4(1H)-ones, which are products of 6-endo-dig cyclization, are formed along with 1H-indazoles, products of 5-exo-dig cyclization. In a DMSO:H2O mixture, 3-aroyl-1H-indazoles are formed exclusively. In the case of 2-[(4-methoxyphenyl)ethynyl]-4-haloanilines, the 5-exo-dig cyclization proceeds independently on the used solvent. Among the prepared trimethoxy-benzoyl-1H-indazoles, the 5-chloro-substituted indazole showed the highest cytotoxicity, while the fluoro-substituted indazole exhibited no severe cytotoxicity.
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Babushkina A. A. et al. The Richter reaction in the synthesis of combretastatin analogs // Russian Chemical Bulletin. 2023. Vol. 72. No. 4. pp. 1012-1022.
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Babushkina A. A., Mikhailov V. N., Ogurtsova A. D., Bunev A. S., Sorokoumov V. N., Balova I. A. The Richter reaction in the synthesis of combretastatin analogs // Russian Chemical Bulletin. 2023. Vol. 72. No. 4. pp. 1012-1022.
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TY - JOUR
DO - 10.1007/s11172-023-3866-3
UR - https://doi.org/10.1007/s11172-023-3866-3
TI - The Richter reaction in the synthesis of combretastatin analogs
T2 - Russian Chemical Bulletin
AU - Babushkina, A A
AU - Mikhailov, V. N.
AU - Ogurtsova, A. D.
AU - Bunev, A S
AU - Sorokoumov, V N
AU - Balova, I A
PY - 2023
DA - 2023/04/01
PB - Springer Nature
SP - 1012-1022
IS - 4
VL - 72
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2023_Babushkina,
author = {A A Babushkina and V. N. Mikhailov and A. D. Ogurtsova and A S Bunev and V N Sorokoumov and I A Balova},
title = {The Richter reaction in the synthesis of combretastatin analogs},
journal = {Russian Chemical Bulletin},
year = {2023},
volume = {72},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11172-023-3866-3},
number = {4},
pages = {1012--1022},
doi = {10.1007/s11172-023-3866-3}
}
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MLA
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Babushkina, A. A., et al. “The Richter reaction in the synthesis of combretastatin analogs.” Russian Chemical Bulletin, vol. 72, no. 4, Apr. 2023, pp. 1012-1022. https://doi.org/10.1007/s11172-023-3866-3.