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

Description

N-(5H-Purin-6-yl)benzamide, also known as N-Benzoylaminopurine, is an organic compound with the chemical formula C12H10N6O. It is a white solid and is primarily used in the organic synthesis of adenine derivative molecules. Adenine is an essential component of nucleic acids, making N-(5H-Purin-6-yl)benzamide a significant compound in the field of molecular biology and pharmaceuticals.

Uses

1. Used in Organic Synthesis:
N-(5H-Purin-6-yl)benzamide is used as a key intermediate in the organic synthesis of adenine derivative molecules. It plays a crucial role in the production of bicyclic adenine nucleosides and oxy-peptide nucleic acids (PNA) through condensation reactions with other molecules like L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(5H-Purin-6-yl)benzamide is utilized for the development of new drugs targeting various diseases. Its involvement in the synthesis of adenine derivatives makes it a valuable compound for creating potential therapeutic agents, particularly those related to nucleic acid metabolism and function.
3. Used in Molecular Biology Research:
N-(5H-Purin-6-yl)benzamide is also employed in molecular biology research, where it is used to study the structure, function, and interactions of nucleic acids. Its role in the synthesis of adenine derivatives allows researchers to explore the properties and potential applications of these molecules in gene regulation, genetic engineering, and other biological processes.
4. Used in the Development of Diagnostic Tools:
Due to its involvement in the synthesis of adenine derivative molecules, N-(5H-Purin-6-yl)benzamide can be used in the development of diagnostic tools and techniques for detecting and analyzing nucleic acid-related disorders. These tools can be valuable in the early detection and treatment of various diseases, including genetic disorders and cancer.

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

• 98-88-4 benzoyl chloride 
• 73-24-5 7H-purin-6-ylamine 
• 93-97-0 benzoic acid anhydride 
• 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 

Downstream Products

• 6984-53-8 N⁶,2',3',5'-tetra-O-benzoyladenosine 
• 155164-96-8 Acetic acid (3S,5R)-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 155164-97-9 Acetic acid (3S,5S)-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 163215-14-3 9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine 
• 161545-38-6 9-(2-O-acetyl-3,5,6-tri-O-benzoyl-β-D-glucofuranosyl)-N⁶-benzoyladenine 
• 160533-31-3 9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine 
• 161545-41-1 9-(2,5,6-tri-O-acetyl-3-O-methanesulfonyl-β-D-glucofuranosyl)-N⁶-benzoyladenine 
• 158531-19-2 (S)-4-[(2S,3S,4R,5R)-3,4-Diacetoxy-5-(6-benzoylamino-purin-9-yl)-2-methyl-tetrahydro-furan-2-ylmethylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester 
• 161614-98-8 9-(2-O-acetyl-5-O-benzoyl-4-benzoyloxymethyl-3-O-methanesulfonyl-β-D-xylofuranosyl)-N⁶-benzoyladenine 
• 160533-28-8 9-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine 
• 51549-15-6 2',3',5'-tri-O-benzoyladenosine 
• 161924-09-0 N⁹-(4-benzyloxy-3-benzyloxymethyl-1,2-butadien-1-yl)adenine 
• 162894-38-4 N⁶-benzoyl-9-(5-O-benzoyl-2,3-di-O-acetyl-3-C-trifluoromethyl-β-D-ribofuranosyl)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.