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About This Item
Linear Formula:
NH2CONHOH
CAS Number:
Molecular Weight:
76.05
Beilstein/REAXYS Number:
1741548
EC Number:
MDL number:
UNSPSC Code:
12352103
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assay
98%
SMILES string
NC(=O)NO
InChI
1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
InChI key
VSNHCAURESNICA-UHFFFAOYSA-N
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Application
Inhibitor of DNA synthesis.
Biochem/physiol Actions
Anti-neoplastic. Inactivates ribonucleoside reductase by forming a free radical nitroxide that binds a tyrosyl free radical in the active site of the enzyme. This blocks the synthesis of deoxynucleotides, which inhibits DNA synthesis and induces synchronization or cell death in S-phase.
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Hugo Martinez-Rojano et al.
Antimicrobial agents and chemotherapy, 52(10), 3642-3647 (2008-08-13)
Leishmania mexicana is a protozoan parasite that causes a disease in humans with frequent relapses after treatment. It is also highly resistant to the currently available drugs. For this reason, there is an urgent need for more effective antileishmanial drugs.
Carl E Wagner et al.
Journal of medicinal chemistry, 52(19), 5950-5966 (2009-10-02)
This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use
Claudia Temperini et al.
Bioorganic & medicinal chemistry letters, 16(16), 4316-4320 (2006-06-09)
N-Hydroxyurea binds both to carbonic anhydrase (CA) and to matrix metalloproteinases (MMPs). X-ray crystallography showed N-hydroxyurea to bind in a bidentate mode by means of the oxygen and nitrogen atoms of the NHOH moiety to the Zn(II) ion of CA
Kesavan Krishnan et al.
Bioorganic & medicinal chemistry letters, 18(23), 6248-6250 (2008-11-04)
Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1:1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were
Ali Khalaj et al.
Bioorganic & medicinal chemistry letters, 16(23), 6034-6038 (2006-09-23)
Two novel dual functional agents, 3[3-(2,4-dinitro-phenylamino)-propyl]-5-fluoro-1H-pyrimidine-2,4-dione 7 and N-[3-(2,4-dinitro-phenylamino)-propoxy]urea 8, resulting from linkage of 2,4-dinitrophenylamine through three carbon atoms with 5-fluorouracil 5 and hydroxyurea 6, respectively, were prepared and their in vitro aerobic cytotoxicities in HT-29 cell line with and
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