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CAS 74131-08-1

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5-[(1E)-2-Chloroethenyl]-2′-deoxyuridine

Description:
5-[(1E)-2-Chloroethenyl]-2′-deoxyuridine, commonly referred to as a nucleoside analog, is characterized by its structural modification of the natural nucleoside deoxyuridine. This compound features a chloroethenyl group at the 5-position of the uracil base, which enhances its antiviral properties. It is primarily studied for its potential use in antiviral therapies, particularly against viruses such as HIV and herpes simplex virus. The presence of the chloroethenyl moiety contributes to its ability to inhibit viral replication by interfering with nucleic acid synthesis. The compound is typically soluble in polar solvents and exhibits stability under physiological conditions, although it may be sensitive to hydrolysis. Its mechanism of action involves incorporation into viral DNA, leading to chain termination during replication. As a synthetic derivative, it is important in medicinal chemistry and virology research, providing insights into the development of effective antiviral agents. Safety and handling precautions are necessary due to its potential biological activity.
Formula:C11H13ClN2O5
InChI:InChI=1/C11H13ClN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
InChI key:InChIKey=LKILSWTYYBIIQE-PIXDULNESA-N
SMILES:O=C1N([C@@H]2O[C@H](CO)[C@@H](O)C2)C=C(/C=C/Cl)C(=O)N1
Synonyms:
  • 5-[(1E)-2-Chloroethenyl]-2′-deoxyuridine
  • Uridine, 5-[(1E)-2-chloroethenyl]-2′-deoxy-
  • Uridine, 5-(2-chloroethenyl)-2′-deoxy-, (E)-
  • E-5-(2-Chlorovinyl)-2′-deoxyuridine
  • See more synonyms
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