CAS 90597-22-1

Cyclopentenylcytosine

Description:

Cyclopentenylcytosine (CPEC) is a nucleoside analog that exhibits unique structural characteristics due to the presence of a cyclopentene ring fused to the cytosine base. This modification enhances its stability and bioactivity compared to natural nucleosides. CPEC is known for its potential antiviral properties, particularly against certain viruses, as it can interfere with viral replication processes. The compound is typically characterized by its ability to mimic natural nucleotides, allowing it to be incorporated into RNA or DNA during synthesis. Its mechanism of action often involves the inhibition of viral polymerases, which are essential for viral genome replication. Additionally, CPEC has been studied for its potential therapeutic applications in cancer treatment, as it may exhibit cytotoxic effects on rapidly dividing cells. The compound's solubility, stability under physiological conditions, and ability to penetrate cellular membranes are also important characteristics that contribute to its biological activity. Overall, cyclopentenylcytosine represents a significant area of research in medicinal chemistry and virology.

Formula: C₁₀H₁₃N₃O₄

InChI: InChI=1S/C10H13N3O4/c11-7-1-2-13(10(17)12-7)6-3-5(4-14)8(15)9(6)16/h1-3,6,8-9,14-16H,4H2,(H2,11,12,17)/t6-,8-,9+/m1/s1

InChI key: InChIKey=DUJGMZAICVPCBJ-VDAHYXPESA-N

SMILES: O[C@H]1[C@@H](C=C(CO)[C@H]1O)N2C(=O)N=C(N)C=C2

Synonyms:

• 2(1H)-Pyrimidinone, 4-amino-1-[4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-, [1R-(1α,4β,5β)]-
• 2(1H)-pyrimidinone, 4-amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-
• 4-Amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone
• Cyclopentenylcytosine
• NSC 375575
• 4-Amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1H)-one
• CPEC

Cyclopentenylcytosine

CAS: 90597-22-1

Formula: C₁₀H₁₃N₃O₄

Color and Shape: White To Off-White Solid

Molecular weight: 239.23

Ref: 4Z-C-952

Cyclopentenyl cytosine

CAS: 90597-22-1

Cyclopentenyl cytosine is a cytotoxic drug that inhibits the synthesis of DNA, RNA, and proteins. It is a nucleoside analogue that inhibits the enzyme activity of ribonucleotide reductase. Cyclopentenyl cytosine has significant cytotoxicity against hl-60 cells, as well as squamous carcinoma and MDA-MB-231 breast cancer cells. It also has significant activity against cyclopentenyl, dextran sulfate, and mitochondrial functions in vivo in human cells. Cyclopentenyl cytosine binds to the response element on the DNA strand, preventing transcription of genes for protein synthesis and cell division.

Formula: C₁₀H₁₃N₃O₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 239.23 g/mol

Ref: 3D-NC58281

Cyclopentenylcytosine

Controlled Product

CAS: 90597-22-1

Formula: C₁₀H₁₃N₃O₄

Color and Shape: Neat

Molecular weight: 239.228

Ref: TR-C989800