14013-11-7

Usage

Uses

Used in Pharmaceutical Industry:
9-Benzylinosine is used as a potential anti-cancer agent for its ability to target and inhibit specific enzymes and pathways involved in cancer cell growth and proliferation.
Used in Biochemical Research:
9-Benzylinosine is used as a nucleic acid modifier to study its effects on gene regulation and the structure and function of nucleic acids, contributing to a better understanding of molecular biology and disease mechanisms.
Used in Drug Development:
9-Benzylinosine is used in the development of new drugs and therapeutic strategies for various diseases, leveraging its unique properties as a modified nucleoside to target specific biological processes and pathways.

InChI:InChI=1/C12H10N4O/c17-12-10-11(13-7-14-12)16(8-15-10)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2,(H,13,14,17)

Upstream product

• 77287-34-4 formamide 
• 3815-69-8 5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide 
• 108160-17-4 Propan-2-one O-(9-benzyl-9H-purin-6-yl)-oxime 
• 122-51-0 orthoformic acid triethyl ester 
• 3287-99-8 benzylamine hydrochloride 
• 68-94-0 hypoxanthine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 68462-61-3 ethyl 5‐amino‐1‐benzyl‐1H‐imidazole‐4‐carboxylate 
• 1422048-55-2 C₂₂H₂₆N₄O 
• 100-46-9 benzylamine 
• 110-86-1 pyridine 
• 4261-14-7 9-benzyl-9H-purin-6-ylamine 
• 73-24-5 7H-purin-6-ylamine 
• 100-44-7 benzyl chloride 

Downstream Products

• 95633-81-1 1-phenacyl-9-benzylhypoxanthine 
• 110287-91-7 1-acetonyl-9-benzylhypoxanthine 
• 4022-95-1 7-benzyl-7H-[1,2,4]triazolo[4,3-g]purine 
• 10553-44-3 7-benzyl-1,2,3,4-tetrazolo[5,1-i]purine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 6268-73-1 9-benzyl-6-hydrazino-9H-purine 
• 7026-49-5 1-benzyl-5-aminoimidazole-4-carboxylic acid benzylamide 

Relevant academic research and scientific papers

N1-substituted hypoxanthine derivatives from the reaction of 6-halopurines with Michael acceptors under the conditions of Heck reaction

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alky

Synthetic method of nitric acid catalyzed hypoxanthine derivative

The invention discloses a synthetic method of a nitric acid catalytic hypoxanthine derivative, and belongs to the technical field of pharmaceutical chemistry. 6 - Chloropurine derivatives were mixed with a solvent, a catalytic amount of nitric acid heating reaction was added, and acid generated in the reaction was neutralized, and the solvent was removed under reduced pressure to obtain a hypoxanthine derivative. The hypoxanthine derivative obtained by the method is low in cost, high in purity and good in substrate adaptability; various impurities in a traditional method are removed; separation and purification are convenient; and the reliability of the quality of the hypoxanthine derivative is improved.

Synthetic studies on compounds related to aminoimidazolecarboxamide: Synthesis of angularly fused purine derivatives and a solid phase ring transformation (ANRORC) to imidazo [1,5-a] pyrazine

l-Benzyl-5-aminoimidazole-4-carboxamide la has been used as a convenient precursor for the synthesis of new triazolo [3,4-i] purines 6 and the corresponding tetrazolo analogue 7. A mesoionic isomer 8 seems to exist along with 7. Interesting heteroaryl-purine motifs have also been prepared via suitably substituted 9-benzyIpurines. Imidazo |I,5-a| pyrazine derivative has been prepared in a solid phase exploitation of suitable imidazolium salt via ANRORC.

Palladium-catalysed Claisen rearrangement of 6-allyloxypurines

6-Allyloxypurines readily undergo palladium-catalysed Claisen rearrangement under mild conditions affording N 1-substituted hypoxanthines. In contrast with the previously reported protocol, the Claisen rearrangement can be performed using Pd(PP

Synthesis of N-aryl uracils and hypoxanthines and their biological properties

1-Benzyluracils 2a,b were treated with iodobenzene in the presence of cuprous oxide in 2,4,6-trimethylpyridine at 180°C to give the N1-phenyl derivatives 3a and 3b in 47% and 55%, respectively. Similar reaction of 2a with 2-bromopyridine at 120°C gave the 3-(2-pyridinyl)uracil 4a in 42% yield. However, unusual product 5 as well as 3-(2-pyridinyl) derivative 4b were obtained in the case of 2b. The structure of 5 was identified as 1- (2,6-difluorobenzyl)-3-[(2,4-dimethyl-2-pyridinyl)methyl]uracil from spectroscopic data. Reaction of the hypoxanthines 7a, b with 2-bromopyridine gave the 1-(2-pyridinyl)hypoxanthines 8a, b in low yields. But N-phenylation of 7a,b were unsuccessful.

THE DEMONSTRATION OF NORMAL O->N CLAISEN REARRANGEMENT IN PURINES

6-Allyloxy-9-benzylpurine (2) and 9-benzyl-6-propargyloxy purine (5) undergo normal thermal O->N rearrangement, either neat or in o-dichlorobenzene.The latter leads to the novel, 1-allenyl-9-benzyl-hypoxanthine (6).The related 4-allyloxy and 4-propargyloxy quinazolines (9, 12) also undergo smooth thermal O->N Claisen rearrangement.In the case of (12), the primary allenic product is further transformed into 3-propargylquinazolin-4-one (13) and the allene dimer (14).

THE CHEMICAL SIMULATION OF THE "ATP-IMIDAZOLE" CYCLE

The synthetic strategy inherent in the "ATP-Imidazole" cycle and centred around the vicinal disposition of -NH2 and -CONH2 functions, has been demonstrated with anthranilamide (2) and 1-benzyl-5-aminoimidazole-4-carboxamide (1) as regeneratable carriers involving specifically N-alkylated quinazolin-4-ones, hypoxantines and adenines, as key intermediates.The isolation and characterization of the enamine (22) coupled with other observations has made it possible to rationalize the pathways involved in these cyclic operations.The practical utility of the synthetic strategy using regeneratable carriers has beem illustrated with the synthesis of a range of 1,5-disubstituted imidazoles.Whilst pathways leading to specific N-alkylation in the Natural cycle and in simulation studies are comparable, the subsequent events take place in a reverse order, primarily because of the divergence in the hydrolitic profile of the alkylated substrates.The action of dilute alkali on 3-alkylated quinazolin-4-ones leads to 2-3 rather than 3-4 bond rupture.Endeavours to promote the latter path, by blocking the 2 position gave unexpected results. 2-Methyl-3-phenacyl quinazolin-4-one gave with dilute alkali the novel aromatic tricyclic system (32) from trans-annular cyclization.On the other hand the 2-blocked 3-benzamido quinazolin-4-ones (33) and (34) gave triazoles (35) and (36) arising from the desired 3-4 rupture followed by cyclization initiated by the resulting amidine unit. 2-Phenil-3-benzamidoquinazolin-4-one (34) with distilled water at 200 deg C gave a number of products whicc have been identified and their formation explained.

The Reaction of 5-Aminoimidazole-4-carbohydrazides with Orthoesters

The reaction of 5-aminoimidazole-4-carbohydrazides with orthoesters is shown to yield 1-amino-9-alkylhypoxanthines.Similar reaction of anthranilic acid hydrazide is shown to yield 3-amino-4-quinazolone, and not 1,4-dihydro-5H-1,3,4-benzotriazepin-5-one as previously reported.

Coupling of Diazopurines, a Curious Steric Effect in a Free Radical Reaction

The reaction of adenine derivatives with nitrite esters in the presence of arenes was examined and found to give 6-arylpurines in good (83percent) to poor (11percent) yield.The arylated products consisted only of the meta and para isomers; none of the anticipated ortho isomers were found.The predominance of meta- and para-substituted products is attributed to steric effects.The evidence that the reaction proceeds via a purine radical includes light stimulation, relative insensitivity to electronic factors, and the facile reaction of the purine intermediate with pyridine N-oxide.Photolysis of 6-iodo-9-benzylpurine in the presence of anisole gave the same mixture of 6-(m-methoxyphenyl)- and 6-(p-methoxyphenyl)purine as did diazotization, suggesting that both reactions involve the same purine radical.