N-Benzoylaminopurine Chemical Properties

Melting point:

242-244°C

Density 

1.494 g/cm3

storage temp. 

2-8°C

Water Solubility 

Insoluble in water

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

11.98±0.20(Predicted)

color 

White to Almost white

BRN 

20585

InChI

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)

InChIKey

QQJXZVKXNSFHRI-UHFFFAOYSA-N

SMILES

C(NC1=C2C(=NC=N1)NC=N2)(=O)C1=CC=CC=C1

CAS DataBase Reference

4005-49-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-43

Safety Statements 

36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Benzoylaminopurine Usage And Synthesis

Chemical Properties

White solid

Uses

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.

Definition

ChEBI: 6-Benzamidopurine is a member of purines.

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.

Synthesis

Benzoyl chloride (1.3 mL, 11 mmol) was added dropwise over 30 min to a stirred suspension of adenine (1.35 g, 10 mmol) in dry pyridine, and stirring was continued at 100 °C for a further 3 h, and the reaction mixture was allowed to stand overnight at room temperature. The reaction was quenched with methanol and the solvents were removed under reduced pressure. The residue was triturated in hot isopropanol and dried in vacuo to give 8 as a white solid: yield 2.15 g (90%). MS (+ESI): m/z 240 [M+H]+; 1H NMR (400 MHz, d-DMSO): δ11.50 (s, 1H), 8.74 (s, 1H), 8.52 (s, 1H), 8.11 (d, 2H, J = 7.2 Hz), 7.66 (t, 1H, J = 7.2 Hz), 7.58 (t, 2H, J = 7.2 Hz).

N-Benzoylaminopurine(4005-49-6)Related Product Information

• Adenine Sulfate
• Chlorantraniliprole
• Adenine phosphate salt（1：1）
• Benzamide
• Adenine
• N6-Benzoyl-2'-deoxyadenosine
• N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
• DMT-2'O-TBDMS-rA(bz) Phosphoramidite
• DMT-dA(bz) Phosphoramidite
• N-BENZOYLADENOSINE
• 5'-O-(4,4'-DIMETHOXYTRITYL)-N6-BENZOYL-2'-DEOXYADENOSINE-3'-O-SUCCINIC ACID
• 3'-DA CEP
• N6,3'-O-DIBENZOYL-2'-DEOXYADENOSINE
• N6-ANISOYLADENOSINE
• N-Benzoylaminopurine
• AURORA 5003
• 5'DIMETHOXYTRITYL DA(BZ)+DG(IBU)+DC(BZ)+T BETA-CYANOETHYL PHOSPHORAMIDITE
• BZ-DMT-DEOXYADENOSINE 2-CLPH DIESTER TRIETHYLAMMONIUM SALT