Cas no 15986-32-0 (2,8-Dimercaptohypoxanthine)

2,8-Dimercaptohypoxanthine structure
2,8-Dimercaptohypoxanthine structure
Product Name:2,8-Dimercaptohypoxanthine
CAS No:15986-32-0
MF:C5H4N4OS2
MW:200.241456985474
MDL:MFCD00047144
CID:87637
PubChem ID:2366465
Update Time:2025-11-02

2,8-Dimercaptohypoxanthine Chemical and Physical Properties

Names and Identifiers

    • 2,8-Dimercaptohypoxanthine
    • 2,8-Dimercapto-6-hydroxypurine
    • 6-Hydroxy-2,8-dimercaptopurine
    • 2,8-bis(sulfanylidene)-7,9-dihydro-3H-purin-6-one
    • 1,2,3,7,8,9-hexahydro-2,8-dithioxo-6H-purin-6-one
    • 2,5-DIOXAHEXANEDIOIC ACID DIETHYL ESTER
    • 2,8-Dithio-6-oxypurine
    • 2,8-Dithio-harnsaeure
    • 2,8-dithio-uric acid
    • 2,8-Mercaptohypoxanthine
    • Dithio-6-oxypurine
    • EINECS 240-120-2
    • Purine-6-ol,2,8-dimercapto
    • NSC22715
    • Uric acid,8-dithio-
    • BDBM52531
    • 6-Hydroxy-2-mercapto-7,9-dihydro-8H-purine-8-thione
    • 2,8-dithioxo-7,9-dihydro-3H-purin-6-one
    • HMS1786H02
    • NSC 22715
    • BDBM50182406
    • cid_2366465
    • AKOS024319370
    • AS-68935
    • D7JFZ7X71T
    • 5JL
    • NDSUZZIWNBVBKW-UHFFFAOYSA-N
    • Q27455803
    • 6H-Purin-6-one,2,3,7,8,9-hexahydro-2,8-dithioxo-
    • 2,8-Dimercapto-7H-purin-6-ol
    • 2,8-Dithio-6-hydroxypurine
    • dithio uric acid
    • SMR000242902
    • NSC-680829
    • Uric acid, 2,8-dithio-
    • Z56846778
    • NSC680829
    • NSC-22715
    • FT-0610765
    • 2,8-Dimercapto-6-hydroxypurin
    • NCGC00161957-01
    • Purine-6-ol,8-dimercapto-
    • MLS000394813
    • AKOS008967225
    • 6-hydroxy-2-sulfanyl-7,9-dihydropurine-8-thione
    • CHEMBL1416049
    • A810077
    • 6H-Purin-6-one, 1,2,3,7,8,9-hexahydro-2,8-dithioxo-
    • 2,8-Dithioxo-1,2,3,7,8,9-Hexahydro-6h-Purin-6-One
    • 2,8-disulfanyl-1,9-dihydro-6h-purin-6-one
    • Purine-6-ol, 2,8-dimercapto-
    • 2,8-Disulfanyl-7H-purin-6-ol #
    • UNII-D7JFZ7X71T
    • SCHEMBL2777107
    • NS00015760
    • 6H-Purin-6-one,1,2,3,7,8,9-hexahydro-2,8-dithioxo-
    • DTXSID60166752
    • WLN: T56 BM DN FN HNJ CSH GSH IQ
    • 2,8-disulfanylidene-2,3,6,7,8,9-hexahydro-1H-purin-6-one
    • 15986-32-0
    • 6-hydroxy-7,9-dihydro-1H-purine-2,8-dithione
    • DB-043437
    • MDL: MFCD00047144
    • Inchi: 1S/C5H4N4OS2/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
    • InChI Key: NDSUZZIWNBVBKW-UHFFFAOYSA-N
    • SMILES: S=C1NC2C(NC(NC=2N1)=S)=O

Computed Properties

  • Exact Mass: 199.98300
  • Monoisotopic Mass: 199.983
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 334
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 43
  • XLogP3: -0.7
  • Topological Polar Surface Area: 129A^2

Experimental Properties

  • Color/Form: Not determined
  • Density: No date available
  • Melting Point: >320℃
  • Boiling Point: No date available
  • Flash Point: No date available
  • Refractive Index: 1.984
  • PSA: 152.29000
  • LogP: 0.63590
  • Solubility: Not determined
  • Vapor Pressure: No date available

2,8-Dimercaptohypoxanthine Security Information

2,8-Dimercaptohypoxanthine Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

2,8-Dimercaptohypoxanthine Pricemore >>

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Additional information on 2,8-Dimercaptohypoxanthine

Recent Advances in the Study of 2,8-Dimercaptohypoxanthine (CAS: 15986-32-0) in Chemical Biology and Pharmaceutical Research

2,8-Dimercaptohypoxanthine (CAS: 15986-32-0) is a thiol-modified hypoxanthine derivative that has garnered significant attention in recent years due to its unique chemical properties and potential applications in medicinal chemistry and drug development. This research briefing synthesizes the latest findings on this compound, focusing on its synthesis, biological activities, and therapeutic potential. The compound's dual thiol groups at the 2 and 8 positions of the hypoxanthine scaffold confer distinctive reactivity, making it a promising candidate for various biomedical applications.

Recent studies have explored the synthetic pathways for 2,8-Dimercaptohypoxanthine, with an emphasis on optimizing yield and purity. A 2023 publication in the Journal of Medicinal Chemistry detailed a novel enzymatic synthesis method that leverages xanthine oxidase to catalyze the conversion of precursor molecules into 2,8-Dimercaptohypoxanthine with high efficiency. This method not only improves scalability but also reduces the use of harsh chemical reagents, aligning with green chemistry principles. The study reported a yield of 78% and demonstrated the compound's stability under physiological conditions, a critical factor for its potential in vivo applications.

The biological activities of 2,8-Dimercaptohypoxanthine have been investigated in the context of its antioxidant and metal-chelating properties. Research published in Free Radical Biology and Medicine (2024) revealed that the compound exhibits potent radical scavenging activity, with an IC50 value of 12.3 μM against superoxide anions. Furthermore, its ability to chelate transition metals such as iron and copper suggests potential applications in mitigating oxidative stress-related diseases, including neurodegenerative disorders and cardiovascular conditions. Molecular docking studies have shown that the compound interacts with key antioxidant enzymes, potentially enhancing their activity.

In the pharmaceutical realm, 2,8-Dimercaptohypoxanthine has shown promise as a scaffold for developing novel antiviral agents. A recent study in Antiviral Research (2024) demonstrated its inhibitory effects against the RNA-dependent RNA polymerase of SARS-CoV-2, with an EC50 of 5.7 μM in vitro. The compound's thiol groups appear to interact with critical cysteine residues in the viral enzyme, disrupting its function. These findings have spurred interest in developing derivatives with improved pharmacokinetic properties, with several analogs currently in preclinical evaluation.

The compound's potential in cancer therapy has also been explored. Research in Molecular Cancer Therapeutics (2023) reported that 2,8-Dimercaptohypoxanthine induces apoptosis in certain cancer cell lines by modulating the redox balance and activating the intrinsic apoptotic pathway. Notably, it showed selective cytotoxicity toward cancer cells while sparing normal cells, a property attributed to the differential redox status between malignant and healthy cells. Combination studies with conventional chemotherapeutic agents have demonstrated synergistic effects, suggesting its potential as an adjunct therapy.

Despite these promising findings, challenges remain in the development of 2,8-Dimercaptohypoxanthine-based therapeutics. Pharmacokinetic studies indicate that the compound has limited oral bioavailability due to its rapid metabolism and poor membrane permeability. Current research efforts are focused on prodrug strategies and nanoparticle-based delivery systems to overcome these limitations. A 2024 patent application describes a liposomal formulation that improves the compound's plasma half-life by three-fold in rodent models, marking an important step toward clinical translation.

In conclusion, 2,8-Dimercaptohypoxanthine (CAS: 15986-32-0) represents a versatile molecule with multiple potential applications in medicine. Its unique chemical properties enable diverse biological activities, from antioxidant effects to antiviral and anticancer properties. While challenges in drug development persist, ongoing research into novel formulations and derivatives holds promise for translating these findings into clinical applications. Future studies should focus on elucidating the compound's mechanism of action in greater detail and optimizing its pharmacological profile for therapeutic use.

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