Isocytosine

Base Information

• Chemical Name: Isocytosine
• CAS No.: 108-53-2
• Molecular Formula: C4H5N3O
• Molecular Weight: 111.103
• Hs Code.: 29335990
• European Community (EC) Number: 203-592-0
• NSC Number: 49118
• DSSTox Substance ID: DTXSID00148350
• Nikkaji Number: J2.864I
• Wikipedia: Isocytosine
• Wikidata: Q10859790
• Metabolomics Workbench ID: 52593
• ChEMBL ID: CHEMBL56260
• Mol file: 108-53-2.mol

Synonyms:isocytosine

Chemical Property of Isocytosine

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 0.019mmHg at 25°C
• Melting Point: 275 °C
• Refractive Index: 1.688
• Boiling Point: 252.7 °C at 760 mmHg
• PKA: 9.59±0.40(Predicted)
• Flash Point: 106.7 °C
• PSA: 72.03000
• Density: 1.55 g/cm³
• LogP: 0.34560
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Slightly)
• Water Solubility.: Soluble in DMF, DMSO, hot water, and AcOH.
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 111.043261792
• Heavy Atom Count: 8
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Isocytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(NC1=O)N
• General Description: Isocytosine derivatives, when linked to the 5-position of methyl β-D-ribofuranoside, exhibit moderate anti-HBV activity, as demonstrated by in vitro cytotoxicity screening using Hep G2 2.2.15 cells. These compounds, synthesized through multi-step processes involving nucleophilic substitutions and deprotection reactions, show potential as antiviral agents, with selective indexes indicating their therapeutic promise against hepatitis B virus.

Technology Process of Isocytosine

There total 40 articles about Isocytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2-aminopyrimidine (109-12-6) → isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7)

Guidance literature:

With Agrobacterium sp. DSM 6136; for 48h;

DOI:10.1016/S0040-4020(97)00301-3

Reference yield: 58.0%

pyrimidin-2-yl-carbamic acid benzyl ester (191487-39-5) → 2-aminopyrimidine (109-12-6) + isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7) + (6-Oxo-1,6-dihydro-pyrimidin-2-yl)-carbamic acid benzyl ester

Guidance literature:

With Rhodococcus erythropolis DSM 6138; In ethanol; for 16h;

DOI:10.1016/S0040-4020(97)00301-3

Reference yield: 49.0%

imidazolo<1,2-a>pyrimidine-5(1H)-one (55662-68-5) → isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7) + 6-bromoimidazolo<1,2-a>-pyrimidine-5(1H)-one (140685-72-9)

Guidance literature:

With N-Bromosuccinimide; In water; 1.) RT, 1 h, 2.) 80 deg C, 1 h;

DOI:10.1248/cpb.40.235

upstream raw materials:

4-methoxypyrimidin-2-amine

2-ethoxypyrimidin-4-one

2-amino-4-chloropyrimidine

malic acid

Downstream raw materials:

2-amino-4-bromopyrimidine

2-amino-5-bromo-1H-pyrimidin-6-one

2-amino-5-nitropyrimidin-4(3H)-one

2-amino-6-oxo-1,6-dihydro-pyrimidine-5-sulfonic acid

Refernces

Synthesis and anti-HBV activity of isocytosine derivatives linked to 5-position of methyl β-p-ribofuranoside

10.3184/030823407X225473

The research presents the synthesis and anti-hepatitis B virus (HBV) activity of isocytosine derivatives linked to the 5-position of methyl β-D-ribofuranoside. The study involves the synthesis of a series of isocytosine derivatives through a multi-step process, utilizing reactants such as d-ribose, tosylation reagents, potassium phthalimide, and various 2-methyl-thiouracils. The synthesized compounds were evaluated for in vitro cytotoxicity against HBV, with some showing moderate activity. The experiments included nucleophilic substitution reactions, deprotection steps using acids like 70% AcOH, and purification through chromatographic techniques. The structures and purities of the synthesized compounds were confirmed using techniques like 1H NMR spectroscopy, EI-MS, and elemental analysis. The anti-HBV activity was screened using the Hep G2 2.2.15 cell method, revealing selective indexes for the compounds that indicated their potential as antiviral agents.

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