4005-49-6

Basic information

• Product Name: N-(5H-Purin-6-yl)benzamide
• Synonyms: 6-BENZOYLAMINOPURINE;6-BENZAMIDOPURINE;N6-BENZOYLAMINOPURINE;N6-BENZOYLADENINE;N-BZ-ADE;N-BENZOYLADENINE;N-BENZOYLAMINOPURINE;N-(5H-Purin-6-yl)benzamide
• CAS NO: 4005-49-6
• Molecular Formula: C₁₂H₉N₅O
• Molecular Weight: 239.23
• EINECS: 2017-001-1
• Product Categories: Purine;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 4005-49-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 242-244°C
• Boiling Point: 443.7 °C at 760 mmHg
• Flash Point: 222.2 °C
• Appearance: /
• Density: 1.491 g/cm³
• Refractive Index: 1.76
• Storage Temp.: 2-8°C
• PKA: 11.98±0.20(Predicted)
• Water Solubility: Insoluble in water
• BRN: 20585
• CAS DataBase Reference: N-(5H-Purin-6-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5H-Purin-6-yl)benzamide(4005-49-6)
• EPA Substance Registry System: N-(5H-Purin-6-yl)benzamide(4005-49-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 4005-49-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 4005-49-6 differently. You can refer to the following data:
1. N-Benzoylaminopurine 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.
2. 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.

InChI:InChI=1/C12H9N5O/c18-12(8-4-2-1-3-5-8)17-11-9-10(14-6-13-9)15-7-16-11/h1-7,9H,(H,13,14,15,16,17,18)

Upstream product

• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 66224-66-6 adenine 
• 65-85-0 benzoic acid 
• 58-61-7 adenosine 
• 188486-26-2 6-N,N-dibenzoyl-2',5'-di-O-(tert-butyldimethylsilyl)adenosine 
• 188486-27-3 6-N,N-dibenzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl)adenine 
• 188486-28-4 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine 
• 188486-40-0 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine 
• 188486-39-7 6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine 
• 188486-37-5 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-vinyl-β-D-xylofuranosyl)adenine 
• 188486-38-6 6-N-benzoyl-9-(2-O-acetyl-3-C-formyl-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine 
• 188486-36-4 6-N-benzoyl-9-(3,5-O-isopropylidene-3-C-vinyl-β-D-xylofuranosyl)adenine 
• 188486-35-3 6-N-benzoyl-9-(3-C-vinyl-β-D-xylofuranosyl)adenine 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 

Downstream Products

• 1214-39-7 6-benzylaminopurine 
• 188118-64-1 Acetic acid (1S,4R)-4-(6-benzoylamino-purin-9-yl)-cyclopent-2-enylmethyl ester 
• 177412-83-8 Acetic acid (2R,3R,4R,5R)-2-(6-benzoylamino-purin-9-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 
• 209112-43-6 Acetic acid (2R,3S,3aS,6S,6aR)-6-acetoxy-2-(6-benzoylamino-purin-9-yl)-hexahydro-thieno[3,2-b]furan-3-yl ester 
• 209112-45-8 Acetic acid (1S,4S,5R,7S,8R)-4-acetoxy-7-(6-benzoylamino-purin-9-yl)-6-oxa-2-thia-bicyclo[3.2.1]oct-8-yl ester 
• 206055-56-3 [(2S,3S,4R,5R)-4-acetoxy-5-(6-benzamidopurin-9-yl)-3-benzyloxy-2-(benzyloxymethyl)tetrahydrofuran-2-yl]methyl acetate 
• 219569-03-6 2',3',5'-tri-O-(4-toluoyl)-N⁶-benzoyladenosine-3',5'(R/S)-2H₂ 
• 60855-35-8 6-benzoylamino-9-trimethylsilylpurine 
• 221301-06-0 (1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one 
• 280574-43-8 N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-4,5,7-tri-O-acetyl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine 

Relevant articles and documents

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Structure-activity relationship study of N N6-benzoyladenine-type BRD4 inhibitors and their effects on cell differentiation and TNF-α production

Bromodomains are epigenetic 'readers' of histone acetylation. The first potent bromodomain and extra-terminal domain (BET) inhibitors, (+)-JQ1 and I-BET762 (also known as GSK525762), were reported in 2010. Some BET inhibitors are already under clinical trial for the treatment of cancers, but so far, only a few chemical scaffolds are available. We have reported potent N N6-benzoyladenine-based inhibitors of BRD4, a BET family member that serves as a key mediator of transcriptional elongation. Here we present an analysis of the structure-activity relationships of these inhibitors. Among the compounds examined, 20, 28 and 29 enhanced all-trans retinoic acid (ATRA)-induced HL-60 cell differentiation and inhibited tumor necrosis factor (TNF)-α production by THP-1 cells.

Microwave-assisted synthesis of amides from various amines and benzoyl chloride under solvent-free conditions: A rapid and efficient method for selective protection of diverse amines

A number of structurally diverse amides were synthesized by reaction of the corresponding amines with benzoyl chloride under microwave irradiation. The proposed procedure ensures short reaction time, high yields, and excellent selectivity and considerably broadens the series of amines as compared to the microwave-assisted synthesis of amides directly from carboxylic acids. It can also be used for selective protection of various amines, including aromatic, aliphatic, and heterocyclic.