B5258
N6-Benzoyladenine
≥99%, powder
Synonym(s):
6-(Benzoylamino)purine, 6-Benzamidopurine, 6-Benzoyladenine, n6-benzoyl adenosine
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About This Item
Empirical Formula (Hill Notation):
C12H9N5O
CAS Number:
Molecular Weight:
239.23
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
MDL number:
Assay:
≥99%
Form:
powder
Solubility:
warm ethanol: 10 mg/mL, clear to slightly hazy, colorless to faintly yellow
Storage temp.:
2-8°C
Product Name
N6-Benzoyladenine, ≥99%
Quality Level
assay
≥99%
form
powder
solubility
warm ethanol: 10 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
O=C(Nc1ncnc2nc[nH]c12)c3ccccc3
InChI
1S/C12H9N5O/c18-12(8-4-2-1-3-5-8)17-11-9-10(14-6-13-9)15-7-16-11/h1-7H,(H2,13,14,15,16,17,18)
InChI key
QQJXZVKXNSFHRI-UHFFFAOYSA-N
Application
N6-Benzoyladenine is used in the organic synthesis of adenine derivative molecules such as bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine and to produce oxy-peptide nucleic acids.
Biochem/physiol Actions
N6-Benzoyladenine comprises of adenine moiety and is a potent inhibitor of bromodomain-containing protein 4 (BRD4). N6-Benzoyladenine modulates tumor necrosis factor α (TNF-α) levels. It elicits cytotoxicity in liver and ileum cancer cells and may serve as a potential candidate agent for cancer chemotherapy.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Repr. 2 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Regulatory Information
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Structure-Activity Relationship Study of N6-Benzoyladenine-Type BRD4 Inhibitors and Their Effects on Cell Differentiation and TNF-alpha Production
Amemiya S, et al.
Chemical & Pharmaceutical Bulletin, 64(9), 1378-1383 (2016)
A E Håkansson et al.
Bioorganic & medicinal chemistry letters, 11(7), 935-938 (2001-04-11)
Synthesis of a 9-mer alpha-L-LNA (alpha-L-ribo configured locked nucleic acid) containing three 9-(2-O,4-C-methylene-alpha-L-ribofuranosyl)adenine nucleotide monomer(s) has been accomplished. The work involved synthesis of the bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine followed by C2'-epimerization.
M Kuwahara et al.
Nucleic acids symposium series, 42(42), 31-32 (2000-04-26)
Syntheses of N-Fmoc delta-amino acids with an ether linkage in the main chain and six different nucleobases on the side chain, Fmoc-NH-C*H(CH2-CH2-B)-CH2-O-CH2-COOH (B = N6-benzoyladenine, thymine, uracil, N-benzoylcytosine, guanine, and N2-isobutyrylguanine) are described. The delta-amino acids were prepared through 8-12
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B5258-25G | 04061833045404 |
| B5258-5G | 04061833045411 |