6-Selenoguanine

Base Information

• Chemical Name: 6-Selenoguanine
• CAS No.: 5375-85-9
• Molecular Formula: C5H4N5Se
• Molecular Weight: 213.0788
• DSSTox Substance ID: DTXSID00968515
• Nikkaji Number: J982.796J
• ChEMBL ID: CHEMBL295864
• Mol file: 5375-85-9.mol

Synonyms:6-selenoguanine

Chemical Property of 6-Selenoguanine

Chemical Property:

• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 213.96319
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)N)[Se]
• General Description: (2-Amino-7H-purin-6-yl)selanyl, also known as 6-selenoguanine, is a selenium-substituted nucleobase analogue that exhibits enhanced photodynamic properties, including a significantly accelerated triplet decay rate compared to its sulfur counterpart, 6-thioguanine. This heavy-atom substitution red-shifts its absorption spectrum while maintaining high triplet yields, making it a promising candidate for photodynamic therapy, particularly in deeper tissue carcinomas. Additionally, 6-selenoguanine demonstrates notable cytotoxicity against certain cancer cell lines, though its instability under UVA light can be mitigated by complexation with ruthenium, improving its therapeutic potential.

Technology Process of 6-Selenoguanine

There total 5 articles about 6-Selenoguanine 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: 100.0%

selenourea (630-10-4) + 2-Amino-6-chloropurin (10310-21-1) → 6-selenoguanine (5375-85-9)

Guidance literature:

In ethanol; for 2h; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejic.201402412

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → 6-selenoguanine (5375-85-9)

Guidance literature:

With selenium; sodium tetrahydroborate; In ethanol; for 48h; Reflux;

Reference yield:

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) → 6-selenoguanine (5375-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 8 h / 0 °C / Reflux

2: selenium; sodium tetrahydroborate / ethanol / 48 h / Reflux

With selenium; sodium tetrahydroborate; trichlorophosphate; In ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

selenourea

2-Amino-6-chloropurin

2-amino-1,9-dihydro-6H-purin-6-one