Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase
Liudmila A Alexandrova
1
,
Vladimir O. Chekhov
2, 3
,
Eduard R Shmalenyuk
1
,
С. Н. Кочетков
1
,
Rania Abu El Asrar
4
,
Piet Herdewijn
4
Publication type: Journal Article
Publication date: 2015-11-01
scimago Q2
wos Q1
SJR: 0.608
CiteScore: 6.7
Impact factor: 3.0
ISSN: 09680896, 14643391
PubMed ID:
26482569
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
A series of 5'-monophosphates of 5-substituted 2'-deoxyuridine analogs, which recently demonstrated in vitro substantial suppression of two strains of Mycobacterium tuberculosis growth (virulent laboratory H37Rv and multiple resistant MS-115), has been synthesized and evaluated as potential inhibitors of M. tuberculosis thymidylate synthases: classical (ThyA) and flavin dependent thymidylate synthase (ThyX). A systematic SAR study and docking revealed 5-undecyloxymethyl-2'-deoxyuridine 5'-monophosphate 3b, displaying an IC50 value against ThyX of 8.32 μM. All derivatives lack activity against the ThyA. It can be assumed that the mechanism of action of 3b may be partially associated with the inhibition of the ThyX.
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GOST
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Alexandrova L. A. et al. Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase // Bioorganic and Medicinal Chemistry. 2015. Vol. 23. No. 22. pp. 7131-7137.
GOST all authors (up to 50)
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Alexandrova L. A., Chekhov V. O., Shmalenyuk E. R., Кочетков С. Н., El Asrar R. A., Herdewijn P. Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase // Bioorganic and Medicinal Chemistry. 2015. Vol. 23. No. 22. pp. 7131-7137.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.bmc.2015.09.053
UR - https://doi.org/10.1016/j.bmc.2015.09.053
TI - Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase
T2 - Bioorganic and Medicinal Chemistry
AU - Alexandrova, Liudmila A
AU - Chekhov, Vladimir O.
AU - Shmalenyuk, Eduard R
AU - Кочетков, С. Н.
AU - El Asrar, Rania Abu
AU - Herdewijn, Piet
PY - 2015
DA - 2015/11/01
PB - Elsevier
SP - 7131-7137
IS - 22
VL - 23
PMID - 26482569
SN - 0968-0896
SN - 1464-3391
ER -
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BibTex (up to 50 authors)
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@article{2015_Alexandrova,
author = {Liudmila A Alexandrova and Vladimir O. Chekhov and Eduard R Shmalenyuk and С. Н. Кочетков and Rania Abu El Asrar and Piet Herdewijn},
title = {Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase},
journal = {Bioorganic and Medicinal Chemistry},
year = {2015},
volume = {23},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/j.bmc.2015.09.053},
number = {22},
pages = {7131--7137},
doi = {10.1016/j.bmc.2015.09.053}
}
Cite this
MLA
Copy
Alexandrova, Liudmila A., et al. “Synthesis and evaluation of C-5 modified 2′-deoxyuridine monophosphates as inhibitors of M. tuberculosis thymidylate synthase.” Bioorganic and Medicinal Chemistry, vol. 23, no. 22, Nov. 2015, pp. 7131-7137. https://doi.org/10.1016/j.bmc.2015.09.053.
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