Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4.
Natalia B Chernysheva
1
,
Anna Maksimenko
2
,
Victor P. Kislyi
1
,
Yuri A. Strelenko
1
,
Marina Semenova
4
,
Victor Semenov
1
Publication type: Journal Article
Publication date: 2018-02-01
scimago Q1
wos Q1
SJR: 1.142
CiteScore: 11.3
Impact factor: 5.9
ISSN: 02235234, 17683254
PubMed ID:
29407976
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
4,5-Diarylisoxazoles are potent antiproliferative tubulin-targeting agents. Their isomeric 3,4-diaryl-5-unsubstituted isoxazoles are hardly accessible. The synthesis of 3,4-diaryl-5-unsubstituted isoxazoles 13 was designed based on a condensation of arylbenzaldehydes, arylnitromethanes, and ethoxycarbonylmethylpyridinium bromide followed by a selective one-step transformation of intermediate 3,4-diaryl-5-ethoxycarbonyl-4,5-dihydroisoxazole 2-oxides 8. The orientation of aryl rings in relation to isoxazole heterocycle was confirmed by X-ray crystallography. Targeted compounds were evaluated for antimitotic microtubule destabilizing activity using a phenotypic sea urchin embryo assay. 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)isoxazole 13e and 13h with a single methoxy substituent were the most potent. Compound 13e showed strong cytotoxicity in NCI60 screen with GI50 for NCI-H522 human lung cancer cell line of 0.023 μM.
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Total citations:
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Citations from 2025:
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(11.76%)
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Chernysheva N. B. et al. Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4. // European Journal of Medicinal Chemistry. 2018. Vol. 146. pp. 511-518.
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Chernysheva N. B., Maksimenko A., Andreyanov F. A., Kislyi V. P., Strelenko Y. A., Khrustalev V. N., Semenova M., Semenov V. Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4. // European Journal of Medicinal Chemistry. 2018. Vol. 146. pp. 511-518.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.ejmech.2018.01.070
UR - https://doi.org/10.1016/j.ejmech.2018.01.070
TI - Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4.
T2 - European Journal of Medicinal Chemistry
AU - Chernysheva, Natalia B
AU - Maksimenko, Anna
AU - Andreyanov, Fedor A
AU - Kislyi, Victor P.
AU - Strelenko, Yuri A.
AU - Khrustalev, Victor N.
AU - Semenova, Marina
AU - Semenov, Victor
PY - 2018
DA - 2018/02/01
PB - Elsevier
SP - 511-518
VL - 146
PMID - 29407976
SN - 0223-5234
SN - 1768-3254
ER -
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BibTex (up to 50 authors)
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@article{2018_Chernysheva,
author = {Natalia B Chernysheva and Anna Maksimenko and Fedor A Andreyanov and Victor P. Kislyi and Yuri A. Strelenko and Victor N. Khrustalev and Marina Semenova and Victor Semenov},
title = {Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4.},
journal = {European Journal of Medicinal Chemistry},
year = {2018},
volume = {146},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.ejmech.2018.01.070},
pages = {511--518},
doi = {10.1016/j.ejmech.2018.01.070}
}
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