Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

B5258

Sigma-Aldrich

N6-Benzoyladenine

≥99%

Synonym(s):

6-(Benzoylamino)purine, 6-Benzamidopurine, 6-Benzoyladenine, n6-benzoyl adenosine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C12H9N5O
CAS Number:
4005-49-6
Molecular Weight:
239.23
MDL number:
MFCD00037927
UNSPSC Code:
41106305
PubChem Substance ID:
24891827
NACRES:
NA.51

Quality Level

200

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

Related Categories

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H361d

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Discovery and structure-activity relationship studies of N6-benzoyladenine derivatives as novel BRD4 inhibitors
Noguchi-Yachide T, et al.
Bioorganic & Medicinal Chemistry, 23(5), 953-959 (2015)
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.
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)
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
Synthesis and cytotoxicity of cyanoborane adducts of n6-benzoyladenine and 6-triphenylphosphonylpurine
Scarlett TC, et al.
Metal-based drugs, 9(1-2), 19-32 (2002)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service