22129-07-3

Usage

Structure

Imidazole ring and phenylmethyl ester group The compound consists of an imidazole ring (a 5-membered ring with 2 nitrogen atoms) and a phenylmethyl ester group (a phenyl group attached to a methyl ester).

Use as an intermediate

Synthesis of pharmaceuticals and organic compounds The compound is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds due to its reactive nature.

Building block for heterocyclic compounds

Facilitates the synthesis of complex molecules The presence of the imidazole ring and phenylmethyl ester group makes it a useful building block for the synthesis of complex heterocyclic compounds.

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 22768-02-1 benzyl ethyl carbonate 
• 16644-57-8 N¹,N⁸-Dicarbobenzoxyhexanediamine 
• 89965-56-0 <3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester 
• 108732-21-4 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone 
• 82892-54-4 1-(benzyloxycarbonyl)-3-ethylimidazolium tetrafluoroborate 
• 39896-97-4 benzyl-carbamic acid benzyl ester 
• 194920-04-2 (S)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester 
• 3459-92-5 DBC 
• 228394-58-9 {9-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester 
• 228394-71-6 carbonic acid 5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester tert-butyl ester 
• 344414-07-9 N-tert-butoxycarbonyl-N-[2-(N⁶-benzyloxycarbonyladenin-9-yl)-ethyl]glycine methyl ester 
• 228394-60-3 N^Cbz-guanosine 
• 228394-63-6 {9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester 
• 228394-59-0 {9-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

BENZIMIDAZOL DERIVATIVES FOR TREATING FILOVIRUS INFECTION

The present invention relates to compounds comprising a benzimidazole scaffold, and the use of such compounds for the treatment of viral diseases. The invention also relates to pharmaceutical compositions comprising said compounds as an active ingredient. In particular the compounds of the invention comprising a benzimidazole scaffold are used for the treatment of filoviruses or retroviruses, and preferably for the treatment of Ebola virus or HIV virus.

High Drug Loading and Sub-Quantitative Loading Efficiency of Polymeric Micelles Driven by Donor-Receptor Coordination Interactions

Polymeric micelles are extensively used for the delivery of hydrophobic drugs, which, however, suffer from unsatisfactory drug loading, colloidal uniformity, formulation stability, and drug release. Herein, we demonstrate a convenient strategy to prepare micelles with ultrahigh drug loading via the incorporation of polymer-drug coordination interactions. An amphiphilic copolymer containing pendant phenylboronic acid as electron acceptor unit was synthesized, which afforded donor-acceptor coordination with doxorubicin to obtain micelles with ultrahigh drug loading (～50%), nearly quantitative loading efficiency (>95%), uniform size, and colloidal stability. Besides, the encapsulated drug can be effectively and selectively released in response to the high reactive oxygen species levels in cancer cells, which potentiated the anticancer efficacy and reduced systemic toxicity. Apart from doxorubicin, the current platform could be extended to other drugs with electron-donating groups (e.g., epirubicin and irinotecan), rendering a simple and robust strategy for enabling high drug loading in polymeric micelles and cancer-specific drug release.

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Two different ways to carry out the chemoselective acylation of 2-amino-8-quinolinol with unique features to generate C2-amides or C8-esters were developed. The coupling reaction with a variety of carboxylic acids using EDCI and DMAP provided C8-ester derivatives, whereas N-heteroaromatic acids were not introduced on the C8-hydroxy group, but rather on the C2-amino group under the same conditions. To obtain C2-amides selectively, the anionic nucleophile from 2-amino-8-quinolinol was treated with less reactive acyl imidazolides or esters.

Synthesis and application of a novel asymmetric azo reagent: 1-(tert-butyl)-2-(4-chlorobenzyl) azodicarboxylate (tBCAD)

A series of novel asymmetric azo reagents, 1-(tert-butyl)-2-(4-substituted benzyl) azodicarboxylate, were prepared. The synthetic process has the advantage of simpleness, easy operation, mild reaction condition and high yield. The 1-(tert-butyl)-2-(4-chlorobenzyl) azodicarboxylate (tBCAD) was selected for its stability and convenience to handle, and its precursor can be recycled by recrystallization with toluene. The tBCAD and DIAD were applied to a wide variety of Mitsunobu reactions. The experimental results showed that the performance of tBCAD in Mitsunobu reaction was comparable to that of DIAD, while the stability of tBCAD was much better than DIAD. Thus, tBCAD can be a novel, stable, effective azo-reagent for the Mitsunobu reaction.

Hyaluronan derivatives bearing variable densities of ferulic acid residues

A synthetic procedure has been developed to conjugate ferulic acid (FA) to an important natural polysaccharide derivative such as hyaluronic acid (HA). The activation of FA with 1,1′-carbonyldiimidazole (CDI) has been investigated. Two reactive intermedia

Rapid and selective spiro-cyclisations of O-centred radicals onto aromatic acceptors

Substituted benzyloxycarbonyloxyl radicals were generated by sensitised photolyses of benzyl oxime carbonates. EPR spectroscopy showed they ring closed exclusively by spiro-cyclisation onto the ipso-C-atoms of the aromatic rings. β-Scission of the alkoxycarbonyloxyls to CO2 and benzyloxyl radicals increasingly competed and became dominant above 270 K. The first rate parameters for spiro-cyclisations of O-centred radicals onto aromatics were obtained by the steady-state kinetic EPR method. Pentafluoro-substitution of the ring substantially reduced the spiro-cyclisation rate. Activation barriers of the spiro-cyclisations were computed by DFT to be about half those of the alternative ortho-cyclisations. Consideration of the TS structures suggested the preference for spiro- over ortho-cyclisation resulted from better overlap of the oxyl SOMO with the aromatic π-system during spiro closure.

Synthesis of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones

A solid-phase synthesis of 5-aminopyrazole has been developed and applied to the preparation of pyrazolo[5,1-d]-[1,2,3,5]tetrazine-4(3H)-ones. In this strategy, a one-pot reaction from 5-aminopyrazoles to the pyrazolo[5,1-d]-[1,2, 3,5]tetrazine-4(3H)-ones which provided the compounds in good yields was demonstrated. Using this synthetic strategy, we prepared a representative set of 16 pyrazolo[5,1-d][l,2,3,5]tetrazine-4(3H)-ones.

Simple method for the preparation of esters from Grignard reagents and alkyl 1-imidazolecarboxylates

The reaction of Grignard reagents with alkyl imidazolecarboxylates, which were prepared from alcohols with carbonyl diimidazole, gave the corresponding esters in good to excellent yields. This method conveniently provides esters from alkyl halides and alcohols by C1-carbon chain extension.

A simple method for the functionalization of naked amino hydroxymethylenebisphosphonic acids via a carbamate bond

A simple and efficient procedure for the synthesis of alkylcarbamate hydroxymethylenebisphosphonic acids is described. Hydroxylated compounds are activated with carbonyldiimidazole and coupled to naked amino hydroxymethylenebisphosphonic acids.