CAS 2880-89-9

5-Chlorouridine

Description:

5-Chlorouridine is a nucleoside analog characterized by the presence of a chlorine atom at the 5-position of the uridine molecule. It consists of a pyrimidine base, specifically uracil, linked to a ribose sugar. This modification can influence its biological activity, particularly in the context of antiviral and anticancer research, as it may interfere with nucleic acid synthesis. 5-Chlorouridine is soluble in water and exhibits properties typical of nucleosides, such as the ability to participate in hydrogen bonding due to its hydroxyl and nitrogen functional groups. Its structure allows it to mimic natural nucleosides, potentially leading to incorporation into RNA during transcription processes. The compound is of interest in medicinal chemistry and molecular biology, where it is studied for its effects on RNA metabolism and its potential therapeutic applications. As with many chemical substances, handling 5-Chlorouridine requires appropriate safety measures due to its biological activity and potential toxicity.

Formula: C₉H₁₁ClN₂O₆

InChI: InChI=1/C9H11ClN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

InChI key: LDCUBKKZHSYQTJ-UAKXSSHOSA-N

SMILES: c1c(c(nc(=O)n1[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O)O)Cl

Synonyms:

• 5-Chloro-1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 5-chloro-1-pentofuranosylpyrimidine-2,4(1H,3H)-dione
• 5-CHLOROURIDINE
• 5-Chloro-D-uridine

5-Chloro-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

CAS: 2880-89-9

5-Chloro-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Formula: C₉H₁₁ClN₂O₆

Purity: 95%

Molecular weight: 278.65

Ref: 54-OR1051792

5-Chlorouridine

CAS: 2880-89-9

5-Chlorouridine, a ribonucleoside, is an inhibitor of RNase A (Ki= 44.5 μM) and eosinophil-derived neurotoxin (EDN) (Ki= 1080.1 μM; IC₅₀= 1462.8 μM). It is utilized in research related to inflammatory diseases and hypereosinophilic syndrome.

Formula: C₉H₁₁ClN₂O₆

Molecular weight: 278.646

Ref: TM-TNU2014

5-Chlorouridine

CAS: 2880-89-9

Ref: 7W-GN1247

5-Chlorouridine

CAS: 2880-89-9

Formula: C₉H₁₁ClN₂O₆

Purity: 95%

Color and Shape: Solid

Molecular weight: 278.6464

Ref: IN-DA002WKV

5-Chlorouridine

Controlled Product

CAS: 2880-89-9

Formula: C₉H₁₁ClN₂O₆

Color and Shape: Neat

Molecular weight: 278.65

Ref: TR-C424100

5-Chlorouridine

CAS: 2880-89-9

5-Chloro-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Formula: C₉H₁₁ClN₂O₆

Purity: 95%

Molecular weight: 278.65

Ref: IN-DG8399

5-Chlorouridine

CAS: 2880-89-9

5-Chlorouridine is a nucleoside with hypochlorous acid. It has been shown to inhibit the growth of tumor cells in tissue culture and to have an inhibitory effect on cervical cancer, which may be due to its ability to inhibit cellular metabolism and DNA synthesis. 5-Chlorouridine inhibits the uptake of uridine by blocking the conversion of uridine into cytosine, thereby preventing DNA synthesis. This prodrug also prevents radiation from inducing mutations in DNA. The molecular modeling study shows that 5-chlorouridine forms hydrogen bonds with hydroxyl groups in RNA, which may be important for its anti-cancer activity.

Formula: C₉H₁₁ClN₂O₆

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 278.65 g/mol

Ref: 3D-NC02866