68462-61-3

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE is used as an intermediate in the synthesis of various organic compounds, contributing to the development of new pharmaceuticals. Its unique structure and functional groups make it a valuable building block in medicinal chemistry for creating novel drug candidates.
Used in Scientific Research:
In the realm of scientific research, ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE is employed as a versatile compound for studying its potential biological and pharmacological activities. Its presence in various chemical reactions and assays aids in understanding its properties and applications in different fields of research.
Used in Chemical Synthesis:
ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE is utilized as a key component in the synthesis of complex organic molecules. Its presence in various chemical reactions allows for the creation of a wide range of compounds with diverse applications in various industries.
Overall, ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE is a multifaceted compound with applications spanning across pharmaceuticals, scientific research, and chemical synthesis, showcasing its potential in contributing to advancements in these fields.

InChI:InChI=1/C13H15N3O2/c1-2-18-13(17)11-12(14)16(9-15-11)8-10-6-4-3-5-7-10/h3-7,9H,2,8,14H2,1H3

Upstream product

• 126921-85-5 1-Benzyl-5-carbamoyl-1H-imidazole-4-carboxylic acid ethyl ester 
• 150464-08-7 ethyl 2-amino-2-cyano-acetate*oxalate 
• 122-51-0 orthoformic acid triethyl ester 
• 100-46-9 benzylamine 
• 32683-02-6 ethyl-2-aminocyano acetate 
• 52579-16-5 ethyl N-(ethoxycarbonylcyanomethyl) formimidate 
• 105-56-6 ethyl 2-cyanoacetate 
• 3849-21-6 ethyl cyanoglyoxylate-2-oxime 
• 123124-90-3 4,5-dicyano-1-(phenylmethyl)-1H-imidazole 
• 126921-84-4 1-Benzyl-5-cyano-1H-imidazole-4-carboxylic acid ethyl ester 

Downstream Products

• 228262-99-5 5-amino-1-benzyl-4-imidazolecarboxylic acid 
• 1354640-92-8 ethyl 4-(benzylamino)-1-methylimidazole-5-carboxylate 
• 1094567-96-0 9-benzyl-1-ethyl-1H-purine-2,6(3H,9H)-dione 
• 1094568-01-0 (R)-9-benzyl-1-ethyl-2-(2-hydroxy-1-phenylethylamino)-1H-purin-6(9H)-one 
• 1094568-02-1 (R)-1-benzyl-5-ethyl-7-phenyl-7,8-dihydro-1H-imidazo[2,1-b]purin-4(5H)-one 
• 1094568-03-2 (R)-1-benzyl-2-bromo-5-ethyl-7-phenyl-7,8-dihydro-1H-imidazo[2,1-b]purin-4(5H)-one 
• 1094567-81-3 C₃₄H₂₉N₅O 
• 101073-82-9 1-Amino-9-benzyl-2-ethyl-1,9-dihydro-purin-6-one 
• 101073-81-8 1-Amino-9-benzyl-2-methyl-1,9-dihydro-purin-6-one 
• 101073-80-7 1-amino-9-benzylhypoxanthine 
• 14013-11-7 9-benzyl-6-hypoxanthine 
• 228263-00-1 9-benzyl-2,6-bis(ethoxycarbonyl)purine 
• 226247-80-9 2-amino-9-benzyl-9H-purine 
• 7674-36-4 9-Benzylpurine-2,6-diamine 

Relevant academic research and scientific papers

Synthesis and anticancer activity of ethyl 5-amino-1-N-substituted-imidazole-4-carboxylate building blocks

A series of 5-amino-1-N-substituted-imidazole-4-carboxylate building blocks was synthesized and assayed for their antiproliferative potential against human cancer cell lines, including HeLa (cervical), HT-29, HCT-15 (colon), A549 (lung), and MDA-MB-231 (breast) cells. The preliminary screening results revealed that several derivatives containing alkyl chains at the N-1 position of the imidazole core demonstrate a certain inhibitory effect on growth and proliferation. A significant effect was observed following ethyl 5-amino-1-dodecyl-1H-imidazole-4-carboxylate (5e) treatment for 72 h. The IC50 value for HeLa cells was 0.737 ± 0.05 μM, whereas that for HT-29 cells was 1.194 ± 0.02 μM. Further investigations revealed that 5e significantly inhibited tumor cell colony formation and migration, and it exhibited antiadhesive effects on HeLa cells as well as antitubulin activity along with the induction of early apoptosis of HeLa and HT-29 cells. In addition, derivative 5e significantly reduced the cell mitochondrial membrane potential in a dose-dependent manner and induced early apoptosis of HeLa and HT-29 cells, indicating that 5e may serve as a lead compound for further drug discovery and development.

Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles

An efficient route is described to an unusual exocyclic 4-β-d-ribofuranosyl-aminoimidazole nucleoside, related 4-N- benzylaminoimidazoles and imidazole analogues of precursors in the de novo biosynthesis of purines, via a regiospecific and stereoselective

DERIVATIVES OF 7,8-DIHYDRO-1H-IMIDAZO[2,1-b]PURIN-4(5H)-ONE AND METHODS OF USE THEREOF

The present invention relates to derivatives of 7,8-dihydro-1H-imidazo[2,1-b]purin-4(5H)-one, compositions thereof and methods of use thereof for treating or preventing pain or an inflammatory disease.

Nucleic acid related compounds. 136. Synthesis of 2-amino- and 2,6-diaminopurine derivatives via inverse-electron-demand Diels-Alder reactions

Thermal inverse-electron-demand Diels-Alder reactions of 5-aminoimidazoles and 2,4,6-tris-(ethoxycarbonyl)-1,3,5-triazine (2) with spontaneous retro-Diels-Alder loss of ethyl cyanoformate and elimination of ammonia give 2,6-bis(ethoxycarbonyl)purines. A report that selective alkaline hydrolysis followed by acid-catalyzed decarboxylation gave 6-(ethoxycarbonyl)purine products was not in harmony with known reactions in purine chemistry. Our reinvestigation has shown that the 6-(ethoxycarbonyl) group undergoes preferential base-promoted hydrolysis, as expected, but regioselectivity for attack of hydroxide at the carbonyl group at C6 is not high (relative to hydrolysis of both C2 and C6 esters). The structure of 9-benzyl-2- (ethoxycarbonyl)purine was determined by X-ray crystallography and confirmed by Curtius rearrangement of the azidocarbonyl analogue to give 2-amino-6- benzylpurine. Acid-catalyzed decarboxylation of the 2,6-dicarboxylate formed during hydrolysis gave 9-benzylpurine, and Curtius rearrangement of 2,6-bis(azidocarbonyl)-9-benzylpurine gave 2,6-diamino-9-benzylpurine. Attempted applications of inverse-electron-demand Diels-Alder reactions of 2 with nucleoside derivatives were problematic.

Imidazodiazepine-4,6-dione. A Novel Xanthine Analogue

The first examples of the imidazodiazepine ring system are reported, the compounds being diones related to xanthine.

Purines, Pyrimidines, and Imidazoles. Part 64. Alkylation and Acylation of Some Aminoimidazoles Related to Intermediates in Purine Nucleotide de novo and Thiamine Biosynthesis

Treatment of ethyl-5-amino-1-benzylimidazole-4-carboxylate with butyl-lithium and methyl iodide gave the 5-N-methylamino derivative (4b) and the 3-methiodide (5) whereas ethyl-5-amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxylate gave both the 5-N-methylamino (6b) and 2-methyl (6d) derivatives.Ethyl 5-amino-1-benzylimidazole-4-carboxylate with acetic anhydride or acetyl chloride gave various products, according to the conditions, including the 5-N-mono- and -N,N-di-acetylamino derivatives (4d) and (4c), respectively, and N,N'-dibenzyloxamide (9).The oxamide also arose from treatment of the imidazole (4a) with formaldehyde. 3-Cyanopropanimidate with ethyl α-amino-α-cyano acetate followed by benzylamine or 2,3-O-isopropylidene-D-ribosylamine afforded ethyl 5-amino-1-benzyl-2-(2-cyanoethyl)imidazole-4-carboxylate and ethyl 5-amino-1-(2,3-O-isopropylidene-α- and β-D-ribofuranosyl)imidazole-4-carboxylates, respectively.Ethyl 5-amino-(2,3-O-isopropylidene-β-D-ribofuranosyl)-2-ethoxycarbonylethylimidazole-4-carboxylate and the corresponding 2-ethoxyethyl nucleoside (6i) were similarly prepared.Oxidation of ethyl 5-amino-2-methylimidazole-4-carboxylate with N-chlorosuccinimide and potassium hydroxide led to ethyl 5-amino-1-benzyl-2-formylimidazole-4-carboxylate and oxidation of the protected 2-ethoxycarbonylethyl nucleoside (6j) with selenium dioxide produced the urea derivative (6l).

Purines, Pyrimidines, and Imidazoles. Part 53. Synthesis of Some 5-Halogeno-analogues of Metiamide and Cimetidine

Ethyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or α,β-D-mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar conversion of ethyl 5-amino-1-t-butylimidazole-4-carboxylate to ethyl 1-t-butyl-5-chloroimidazole-4-carboxylate, and removal of the t-butyl group with hydrogen bromide.Ethyl 5-fluoroimidazole-4-carboxylate has been prepared from ethyl 5-amino-1-t-butylimidazole-4-carboxylate by diazotisation and photolysis in the presence of tetrafluoroboric acid.Ethyl 5-chloroimidazole-4-carboxylate and ethyl 5-fluoroimidazole-4-carboxylate have been converted into the corresponding alcohols by reaction with lithium aluminium hydride. 5-Chloro-4-(hydroxymethyl)imidazole has also been prepared by electrolysis of 5-chloroimidazole-4-carboxylic acid at mercury cathode. 5-Chloroimidazole has been converted into the 5-chloroimidazolyl analogues of metiamide and cimetidine by a sequence of reactions, and 5-fluoroimidazole has been similarly converted into the 5-fluoro-analogue of metiamide.The metiamide and cimetidine analogues were found to be histamine H2-receptor antagonists.