CAS 892-49-9

9-β-D-Arabinofuranosyl-1,9-dihydro-6H-purine-6-thione

Description:

9-β-D-Arabinofuranosyl-1,9-dihydro-6H-purine-6-thione, commonly referred to as ARA-A, is a nucleoside analog with notable antiviral properties. It is characterized by its purine base structure, which is modified by the presence of a thione group at the 6-position, contributing to its biological activity. The compound features a β-D-arabinofuranosyl sugar moiety, which is essential for its incorporation into nucleic acids. ARA-A exhibits a broad spectrum of antiviral activity, particularly against certain viruses, making it of interest in medicinal chemistry and virology. Its mechanism of action typically involves the inhibition of viral replication by interfering with nucleic acid synthesis. The compound is soluble in water and exhibits stability under physiological conditions, although its pharmacokinetics and metabolism can vary. As a synthetic derivative, it is often studied for its potential therapeutic applications, particularly in the treatment of viral infections. Safety and efficacy profiles are crucial for its development in clinical settings.

Formula: C₁₀H₁₂N₄O₄S

InChI: InChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7+,10-/m1/s1

InChI key: InChIKey=NKGPJODWTZCHGF-UHTZMRCNSA-N

SMILES: O[C@@H]1[C@H](N2C3=C(N=C2)C(=S)N=CN3)O[C@H](CO)[C@H]1O

Synonyms:

• 6-Mercapto-9-(β-<span class="text-smallcaps">D</span>-arabinofuranosyl)purine
• 6-Thio-9-beta-D-arabinofuranosylpurine
• 6-Thio-9-β-<span class="text-smallcaps">D</span>-arabinofuranosylpurine
• 6H-Purine-6-thione, 9-beta-D-arabinofuranosyl-1,9-dihydro- (9CI)
• 6H-Purine-6-thione, 9-β-<span class="text-smallcaps">D</span>-arabinofuranosyl-1,9-dihydro-
• 6MP-Arabinoside
• 9-(β-<span class="text-smallcaps">D</span>-Arabinofuranosyl)-6-mercaptopurine
• 9-beta-D-Arabinofuranosyl-1,9-dihydro-6H-purine-6-thione
• 9-beta-D-Arabinofuranosyl-9H-purine-6-thiol
• 9-beta-D-arabinofuranosyl-3,9-dihydro-6H-purine-6-thione
• 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-1,9-dihydro-6H-purine-6-thione
• 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-9H-purine-6-thiol
• 9-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-9H-purine-6-thione
• 9H-Purine-6-thiol, 9-β-<span class="text-smallcaps">D</span>-arabinofuranosyl-
• 9H-purine-6-thiol, 9-beta-D-arabinofuranosyl-
• 9beta-Arabinofuranosyl-9-H-purine-6-thiol, D-
• Ara-6Mp
• Ara-MP
• Arabinofuranosyl-6-mercaptopurine
• Arabinosyl-6-mercaptopurine
• Brn 5297846
• Nsc 406021
• beta-Ara-6-MP
• beta-D-Arabinofuranosyl-6-mercaptopurine
• beta-D-Arabinosyl-6-mercaptopurine
• β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-6-mercaptopurine
• β-<span class="text-smallcaps">D</span>-Arabinosyl-6-mercaptopurine
• β-D-Arabinofuranosyl-6-mercaptopurine
• 9-β-D-Arabinofuranosyl-1,9-dihydro-6H-purine-6-thione
• 9H-Purine-6-thiol, 9-β-D-arabinofuranosyl-

6-Thio-9-(β-D-arabinofuranosyl)purine

CAS: 892-49-9

6-Thio-9-(b-D-arabinofuranosyl)purine is a purine analog that inhibits the enzyme uridine phosphorylase, which is involved in the metabolism of uridine. It has been shown to inhibit the growth of L1210 cells and also to be effective against subcutaneous tumors in mice. 6-Thio-9-(b-D-arabinofuranosyl)purine is active against schistosomiasis in mice, with an LD50 of 1 mg/kg. This drug has also been shown to have potential antitumor activity and was able to inhibit the growth of human lymphocytes and leukocytes.

Formula: C₁₀H₁₂N₄O₄S

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 284.29 g/mol

Ref: 3D-NM06321