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696-07-1 | 5-Iodouracil
CAS No: 696-07-1 Catalog No: AG003MTD MDL No:MFCD00006020
Product Description
Catalog Number:
AG003MTD
Chemical Name:
5-Iodouracil
CAS Number:
696-07-1
Molecular Formula:
C4H3IN2O2
Molecular Weight:
237.9833
MDL Number:
MFCD00006020
IUPAC Name:
5-iodo-1H-pyrimidine-2,4-dione
InChI:
InChI=1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI Key:
KSNXJLQDQOIRIP-UHFFFAOYSA-N
SMILES:
Ic1c[nH]c(=O)[nH]c1=O
EC Number:
211-788-2
UNII:
H59BRK500M
NSC Number:
57848
Properties
Complexity:
199
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
237.924g/mol
Formal Charge:
0
Heavy Atom Count:
9
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
237.984g/mol
Monoisotopic Mass:
237.924g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
58.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0
Literature
| Title | Journal |
|---|---|
| Protonation preferentially stabilizes minor tautomers of the halouracils: IRMPD action spectroscopy and theoretical studies. | Journal of the American Society for Mass Spectrometry 20120901 |
| C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells. | European journal of pharmacology 20111215 |
| Chimeric aptamers in cancer cell-targeted drug delivery. | Critical reviews in biochemistry and molecular biology 20111201 |
| Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine. | Bioorganic & medicinal chemistry 20100901 |
| Herpes simplex virus-1 helicase-primase: roles of each subunit in DNA binding and phosphodiester bond formation. | Biochemistry 20091103 |
| Structures of native human thymidine phosphorylase and in complex with 5-iodouracil. | Biochemical and biophysical research communications 20090904 |
| Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents. | Molecules (Basel, Switzerland) 20090727 |
| [Myocardial single photon emission tomography imaging of reporter gene expression in rabbits]. | Zhonghua xin xue guan bing za zhi 20090601 |
| Aluminium(III), chromium(III) and iron(III) complexes with 5-iodouracil and 5-iodouracil-histidine and their antitumour activity. | Journal of enzyme inhibition and medicinal chemistry 20090201 |
| Redetermination of 5-iodo-uracil. | Acta crystallographica. Section E, Structure reports online 20080201 |
| A simple crosslinking method, CLAMP, to map the sites of RNA-contacting domains within a protein. | Methods in molecular biology (Clifton, N.J.) 20080101 |
| Functionalization of unprotected uracil derivatives using the halogen-magnesium exchange. | Organic letters 20070426 |
| Synthesis of novel 2'-methyl carbovir analogues as potent antiviral agents. | Archives of pharmacal research 20070201 |
| N-1 regioselective Michael-type addition of 5-substituted uracils to (2-hydroxyethyl) acrylate. | Beilstein journal of organic chemistry 20070101 |
| Synthesis of new, base-modified PNA monomers. | Nucleosides, nucleotides & nucleic acids 20070101 |
| The DNA N-glycosylase MED1 exhibits preference for halogenated pyrimidines and is involved in the cytotoxicity of 5-iododeoxyuridine. | Cancer research 20060801 |
| Simple synthesis of novel acyclic (e)-bromovinyl nucleosides as potential antiviral agents. | Nucleosides, nucleotides & nucleic acids 20060101 |
| Evaluation of novel one-electron reduction with metal in DNA. | Nucleic acids symposium series (2004) 20060101 |
| Identification of base-specific contacts in protein-DNA complexes by photocrosslinking and mass spectrometry: a case study using the restriction endonuclease SsoII. | Molecular bioSystems 20050701 |
| Influence of halogenation on the properties of uracil and its noncovalent interactions with alkali metal ions. Threshold collision-induced dissociation and theoretical studies. | Journal of the American Chemical Society 20041215 |
| A protein sensor for siRNA asymmetry. | Science (New York, N.Y.) 20041119 |
| Highly efficient photochemical 2'-deoxyribonolactone formation at the diagonal loop of a 5-iodouracil-containing antiparallel G-quartet. | Journal of the American Chemical Society 20040526 |
| Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. | Nucleosides, nucleotides & nucleic acids 20040101 |
| Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine. | Bioorganic & medicinal chemistry letters 20030310 |
| Efficient C2'alpha-hydroxylation of deoxyribose in protein-induced Z-form DNA. | Journal of the American Chemical Society 20030212 |
| Photoreactivity of 5-iodouracil-containing telomeric DNA. | Nucleic acids research. Supplement (2001) 20030101 |
| Nucleobase modified peptide nucleic acid. | Nucleosides, nucleotides & nucleic acids 20030101 |
| Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase. | Journal of medicinal chemistry 20020912 |
| Crystal structure of the productive ternary complex of dihydropyrimidine dehydrogenase with NADPH and 5-iodouracil. Implications for mechanism of inhibition and electron transfer. | The Journal of biological chemistry 20020412 |
| Photoreactivity of 5-iodouracil-containing DNA-Sso7d complex in solution: the protein-induced DNA kink causes intrastrand hydrogen abstraction from the 5-methyl of thymine at the 5' side. | Journal of the American Chemical Society 20020313 |
| Synthesis of 1-(2-hydroxy-3-methoxypropyl)uracils and their activity against L1210 and macrophage raw 264.7 cells. | Nucleosides, nucleotides & nucleic acids 20020101 |
| Mass spectrometric analysis of a UV-cross-linked protein-DNA complex: tryptophans 54 and 88 of E. coli SSB cross-link to DNA. | Protein science : a publication of the Protein Society 20011001 |
| N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution. | The Journal of organic chemistry 20010406 |
| Synthesis of pyrrolidine C-nucleosides via Heck reaction. | Organic letters 20010208 |
| Photoreactivity of 5-iodouracil-containing DNA-Z alpha complex. | Nucleic acids research. Supplement (2001) 20010101 |
| Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii. | Biochemical pharmacology 19940817 |
| Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates. | Journal of medicinal chemistry 19860401 |
| Interaction of monoclonal antibodies directed against bromodeoxyuridine with pyrimidine bases, nucleosides, and DNA. | Journal of immunology (Baltimore, Md. : 1950) 19860301 |
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