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Synthesis and evaluation of 5'-modified thymidines and 5-hydroxymethyl-2'-deoxyuridines as Mycobacterium tuberculosis thymidylate kinase inhibitors
- Source :
- BIOORGANIC & MEDICINAL CHEMISTRY, Bioorganic and Medicinal Chemistry, Bioorganic and Medicinal Chemistry, Elsevier, 2013, 21 (1), pp.257-68. ⟨10.1016/j.bmc.2012.10.018⟩, Bioorganic and Medicinal Chemistry, 2013, 21 (1), pp.257-68. ⟨10.1016/j.bmc.2012.10.018⟩
- Publication Year :
- 2013
-
Abstract
- International audience; We report the synthesis of 5'-modified thymidines (16, 18, 21, 23) and 5,5'-bis-substituted 2'-deoxyuridine analogues (30, 47) as inhibitors of thymidine monophosphate kinase of Mycobacterium tuberculosis (TMPKmt). These analogues were evaluated for their capacity to inhibit TMPKmt and solely two 5'-modified thymidines were found to possess moderate inhibitory activity. In addition, a feasibility study of protecting groups for the 5-CH(2)OH moiety of 2'-deoxyuridines is described that enables to introduce the desired 5'-modification.
- Subjects :
- MESH: Mycobacterium tuberculosis
[SDV]Life Sciences [q-bio]
Clinical Biochemistry
Antitubercular Agents
Pharmaceutical Science
01 natural sciences
Biochemistry
chemistry.chemical_compound
Thymidine monophosphate kinase
DESIGN
Nucleoside analogues
Drug Discovery
Moiety
Hydroxymethyl
MESH: Tuberculosis
biology
Drug discovery
3. Good health
Chemistry
Molecular Medicine
Inhibitor
Stereochemistry
010402 general chemistry
Thymidylate kinase
Mycobacterium tuberculosis
MONOPHOSPHATE KINASE
Humans
Tuberculosis
Molecular Biology
Phosphate bioisosteres
MESH: Humans
ANALOGS
010405 organic chemistry
Organic Chemistry
5-Hydroxymethyl pyrimidines
IN-VITRO
DNA
biology.organism_classification
MESH: Antitubercular Agents
Deoxyuridine
In vitro
0104 chemical sciences
DRUG DISCOVERY
REDUCTION
chemistry
Nucleoside-Phosphate Kinase
MESH: Nucleoside-Phosphate Kinase
MESH: Thymidine
Thymidine
Subjects
Details
- Language :
- English
- ISSN :
- 09680896 and 14643391
- Database :
- OpenAIRE
- Journal :
- BIOORGANIC & MEDICINAL CHEMISTRY, Bioorganic and Medicinal Chemistry, Bioorganic and Medicinal Chemistry, Elsevier, 2013, 21 (1), pp.257-68. ⟨10.1016/j.bmc.2012.10.018⟩, Bioorganic and Medicinal Chemistry, 2013, 21 (1), pp.257-68. ⟨10.1016/j.bmc.2012.10.018⟩
- Accession number :
- edsair.doi.dedup.....c2ca6afbcc1db300c88c619cdf2e2ca2
- Full Text :
- https://doi.org/10.1016/j.bmc.2012.10.018⟩