51721-21-2

Basic information

• Product Name: ethyl 4-tert-butyl-1H-iMidazole -5-carboxylate
• Synonyms: ethyl 4-tert-butyl-1H-iMidazole -5-carboxylate;4-(1,1-Dimethylethyl)-1H-imidazole-5-carboxylic acid ethyl ester;5-(1,1-Dimethylethyl)-1H-imidazole-4-carboxylic acid ethyl ester;1H-Imidazole-5-carboxylic acid, 4-(1,1-dimethylethyl)-, ethyl ester;methyl 4-(tert-butyl)-1H-imidazole-5-carboxylate
• CAS NO: 51721-21-2
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.24624
• Mol File: 51721-21-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.077±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: ethyl 4-tert-butyl-1H-iMidazole -5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-tert-butyl-1H-iMidazole -5-carboxylate(51721-21-2)
• EPA Substance Registry System: ethyl 4-tert-butyl-1H-iMidazole -5-carboxylate(51721-21-2)

Safety Data

• Hazardous Substances Data: 51721-21-2(Hazardous Substances Data)

Usage

General Description

Ethyl 4-tert-butyl-1H-imidazole-5-carboxylate is a chemical compound with a molecular formula of C12H20N2O2. It belongs to the chemical class of imidazoles which are organic compounds containing an imidazole ring, a five-member ring with two non-adjacent nitrogen atoms. ethyl 4-tert-butyl-1H-imidazole -5-carboxylate may be used in a variety of scientific applications, such as a precursor in the synthesis of other organic compounds or as a reagent in chemical reactions. It is also commonly used in the pharmaceutical industry for drug discovery and manufacturing. Its properties such as solubility, melting point, boiling point, etc. may vary according to the conditions it is subjected to.

Upstream product

• 29509-07-7 2-chloro-4,4-dimethyl-3-oxopentanoic acid ethyl ester 
• 77287-34-4 formamide 
• 17094-34-7 ethyl pivaloylacetate 
• 714273-89-9 5-(tert-butyl)oxazole-4-carboxylic acid ethyl ester 
• 2999-46-4 Ethyl isocyanoacetate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 51721-22-3 (4-(tert-butyl)-1H-imidazol-5-yl)methanol 
• 714273-83-3 4-tert-butyl-1H-imidazole-5-carbaldehyde 
• 714272-27-2 (3Z,6Z)-3-[[5-(1,1-dimethylethyl)-1H-imidazol-4-yl]methylene]-6-(phenylmethylene)piperazine-2,5-dione 
• 1367709-16-7 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-phenylmethylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-29-4 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-methoxyphenyl)methylidene]-2,5-piperazinedione 
• 1367717-84-7 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-methoxyphenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-28-3 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(4-methoxyphenyl)methylidene]-2,5-piperazinedione 
• 714272-36-3 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2,3-dimethoxyphenyl)methyllidene]-2,5-piperazinedione trifluoroacetate 
• 714272-33-0 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2,4-dimethoxyphenyl)methylidene]-2,5-piperazinedione 
• 1367720-57-7 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2,5-dimethoxyphenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-34-1 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3,4-dimethoxyphenyl)methylidene]-2,5-piperazinedione 
• 714272-83-0 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-methylphenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-81-8 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-fluorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-77-2 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-fluorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 

Relevant articles and documents

Development of MBRI-001, a deuterium-substituted plinabulin derivative as a potent anti-cancer agent

Plinabulin, a drug targeting microtubule of cancer cells, has been currently tried in its phase III clinical study. However, low efficacy caused by poor pharmacokinetic (PK) properties has been considered to be the main obstacle to approved by the Food and Drug Administration. Herein, we introduced a deuterium atom as an isostere in its structure to become a new compound named (MBRI-001, No. 9 in a series of deuterium-substituted compounds). The structure of MBRI-001 was characterized by HRMS, NMR, IR and a single crystal analysis. MBRI-001 exhibited better pharmacokinetic characteristics than that of plinabulin. Additionally, its antitumor activity is in a low nanomolar level for a variety of cancer cell lines and high activity against human NCI-H460 xenograted in mice intravenous administration. Importantly, continuous administration of MBRI-001 exhibited lower toxicity compared to docetaxel. We thus suggest that MBRI-001 could be developed as a promising anti-cancer agent in near future.

Preparation and purification method of high-purity Plinabulin compound

The invention provides a preparation and purification method of high-purity Plinabulin compound, which aims at mainly removing a trans-isomer. The preparation and purification method has the advantages that (3Z,6Z)-3-benzylidene-6-((5-tert-butyl-1H-imidazole-4-yl)methylene)piperazine-2,5-diketone monohydrate and (3Z,6Z)-3-benzylidene-6-((5-tert-butyl-1H-imidazole-4-yl)deuterated methylene)piperazine-2,5-diketone monohydrate are prepared; the purity of the prepared product is higher than 99.5%, and the content of the trans-isomer is smaller than 0.1%. The invention also relates to the preparation and purification of important intermediates, such as 5-(tert-butyl)-1H-imidazole-4-ethyl formate and 1,4-diacetylpiperazine-2,5-diketone. The preparation and purification method has the advantages that the production cost is reduced, the pos-treatment difficulty is decreased, and the technology more meets the requirements of industrialized production.

Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 μM) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated.