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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.

4005-49-6

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4005-49-6 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 4005-49-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,0 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4005-49:
(6*4)+(5*0)+(4*0)+(3*5)+(2*4)+(1*9)=56
56 % 10 = 6
So 4005-49-6 is a valid CAS Registry Number.
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)

4005-49-6 Well-known Company Product Price

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  • TCI America

  • (B3344)  N6-Benzoyladenine  >98.0%(HPLC)(T)

  • 4005-49-6

  • 5g

  • 890.00CNY

  • Detail
  • TCI America

  • (B3344)  N6-Benzoyladenine  >98.0%(HPLC)(T)

  • 4005-49-6

  • 25g

  • 2,450.00CNY

  • Detail
  • Alfa Aesar

  • (L08292)  N-Benzoylaminopurine, 99%   

  • 4005-49-6

  • 1g

  • 516.0CNY

  • Detail
  • Alfa Aesar

  • (L08292)  N-Benzoylaminopurine, 99%   

  • 4005-49-6

  • 5g

  • 1836.0CNY

  • Detail
  • Alfa Aesar

  • (L08292)  N-Benzoylaminopurine, 99%   

  • 4005-49-6

  • 25g

  • 7084.0CNY

  • Detail

4005-49-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(5H-Purin-6-yl)benzamide

1.2 Other means of identification

Product number -
Other names N-(7H-Purin-6-yl)benzamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4005-49-6 SDS

4005-49-6Relevant articles and documents

Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors

Liu, Qing,Cai, Xiaoqing,Yang, Dehua,Chen, Yi,Wang, Yafang,Shao, Liming,Wang, Ming-Wei

, p. 4579 - 4594 (2017/10/05)

A series of cycloalkyl substituted analogues of the natural product sinefungin lacking the amino-acid moiety was designed and synthesized. Two stereoisomers (6-R and 6-S) were separated and their bioactivities examined against EHMT1/2. Of which, compound 14d showed an inhibitory activity against EHMT1/2 (88.9%, IC50 = 21.8 μM for EHMT1 and 77.6%, IC50 = 39.6 μM for EHMT2, respectively) similar to that of sinefungin (100.0%, IC50 = 28.4 μM for EHMT1 and 79.5%, IC50 = 30.1 μM for EHMT2, respectively). Further studies against other methyltransferases such as PRMT1 showed no activity except that 12d displayed about 20% inhibition.

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

Amemiya, Seika,Yamaguchi, Takao,Sakai, Taki,Hashimoto, Yuichi,Noguchi-Yachide, Tomomi

, p. 1378 - 1383 (2016/09/09)

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.

PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS

-

, (2011/10/13)

Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moie

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

Li, Yanqiu,Wang, Yulu,Wang, Jinye

, p. 358 - 361 (2008/12/22)

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.

Microwave-promoted conversion of heterocyclic amines to corresponding amides under solvent-free conditions

Li, Yanqiu,Wang, Yulu,Wang, Jinye

, p. 251 - 256 (2008/03/14)

An array of heterocyclic amides was synthesized efficiently by combining corresponding amines and benzoyl chloride in one-pot under microwave irradiation. The reaction times were shorter, yields were higher. What is more, the regioselectivity was excellent, which made the protocol support us an entry to selective protection of diverse amino groups.

Design, development and synthesis of a novel labeled PNA monomer incorporated in DNA-hexamer to act as a hybridization probe by FRET

Shukla, Vibha,Mishra, Satyendra,Watal, Geeta,Misra, Krishna

, p. 121 - 129 (2007/10/03)

A novel PNA monomer with adenine nucleobase and a modified backbone with charged -N+-H and a methylene substituted for 2 bond on the lefthand side sign C=O in the linker arm has been synthesised. This modified PNA monomer is further linked with

Novel and efficient syntheses of 3′,5′-diamino derivatives of 2′,3′,5′-trideoxycytidine and 2′,3′,5′-trideoxyadenosine. Protonation behavior of 3′,5′-diaminonucleosides

Lavandera, Iván,Fernández, Susana,Ferrero, Miguel,Gotor, Vicente

, p. 5449 - 5456 (2007/10/03)

High yielding synthetic routes to 3′,5′-diamino-2′,3′,5′-trideoxycytidine and 3′,5′-diamino-2′,3′,5′-trideoxyadenosine are described. In addition, the protonation behavior of 3′,5′-diamino-2′,3′,5′-trideoxycytidine, 3′,5′-diamino-2′,3′,5′-trideoxyadenosin

Studies on the mechanism of ribonucleotide reductases

Lenz, Roman,Giese, Bernd

, p. 2784 - 2794 (2007/10/03)

Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 · 106 s-1 in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 103 times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

Preparation of 1′-c deuterated synthons for RNA synthesis by H-phosphonate method aiming at two-dimensional NMR secondary structure studies

Arnold, Lubos,Pressova, Martina,Saman, David,Vogtherr, Martin,Limmer, Stefan

, p. 389 - 403 (2007/10/03)

1′-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1′-2H]ribose. The procedure included nucleosidation of 1′-O-acetyl-2′,3′,5'-O-tribenzoyl[1′- 2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5′-G* C*U*A*U*UUAU-3′ and 3′-AC* G*A*U*A*AAGU-5′ was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding nondeuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.

Ozonolysis of 6-N-Benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine and Relateds Compounds

Joshi, Bhalchandra V.,Reese, Colin B.

, p. 5807 - 5810 (2007/10/02)

The nucleoside 4',5'-olefins 3, 5, 7 and 9 are readily converted into the corresponding lactones 4, 6, 8 and 10, respectively, by ozonolysis in dichloromethane solution at -78 deg C.

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