33235-31-3

Upstream product

• 21190-16-9 ethyl 4-amino-5-imidazolecarboxylate 
• 3849-21-6 ethyl cyanoglyoxylate-2-oxime 
• 150464-08-7 ethyl 2-amino-2-cyano-acetate*oxalate 
• 21190-16-9 5-amino-1H-imidazole-4-carboxylic acid ethyl ester 
• 76182-23-5 ethyl 5-amino-1-t-butylimidazole-4-carboxylate 

Downstream Products

• 89676-57-3 ethyl 2-<(p-bromophenyl)azo>-4-fluoroimidazole-5-carboxylate 
• 89676-59-5 ethyl 2,4-difluoroimidazole-5-carboxylate 
• 617-36-7 Ethyl oxamate 

Relevant academic research and scientific papers

Photochemical Schiemann reaction in ionic liquids

Photochemical Schiemann reactions of imidazole derivatives 1 and 4 were carried out in 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid [bmim][BF4] as solvent. The effects of temperature, co-solvent and wavelength on the rate of the reaction and product yield were examined. The use of ionic liquid increases the yield of the photochemical fluorodediazoniation reaction of 2 at 0 °C. Careful temperature control is necessary to minimize the photodecomposition of the ionic liquid in order to increase the yield of product.

Ketone-substituted heterocyclic compound and anesthetic effect thereof

The invention discloses a ketone-substituted heterocyclic compound and an anesthetic effect thereof. Specifically provided are a compound represented by formula I, a pharmaceutically acceptable salt thereof, a stereoisomer thereof, or a deuterated derivative thereof. The ketone-substituted heterocyclic compound provided by the invention has a good central nervous system inhibition effect, can generate sedative, hypnotic and/or general anesthesia effects, and can control the epilepsy persistent state; the ketone-substituted heterocyclic compound also has the characteristics of quick response and quick recovery while maintaining excellent anesthetic activity; meanwhile, the ketone-substituted heterocyclic compound has almost no inhibition effect on the adrenal cortex function, has small sideeffects, solves the technical problems in the field, and provides a new choice for clinically screening and/or preparing sedative, hypnotic and/or general anesthesia medicines and medicines for controlling the epilepsy persistent state.

SUBSTITUTED IMIDAZOLECARBOXYLATE DERIVATIVES AND THE USE THEREOF

A compound is shown in formula (I). The derivatives of the compound include a stereoisomer, a pharmaceutically acceptable salt, a solvate, a prodrug, a metabolite, a deuterated derivative. The compound is a structurally novel substituted imidazole formate derivative. Substituted imidazole formate derivatives are used in preparing a drug with sedative, hypnotic and/or anesthetic effects, as well as a drug that can control the state of epilepsy. The compound has a good inhibitory effect on the central nervous system, and provides a new option for clinical screening of and/or preparation of a drug with sedative, hypnotic and/or anesthetic effects and controlling the state of epilepsy.

Substituted imidazole formate type derivative and application thereof

The invention discloses a compound shown as a formula I or a stereoisomer thereof or pharmaceutically acceptable salts thereof or a solvate thereof or a prodrug thereof or a metabolic product thereofor a deuterated derivative thereof. The compound is a substituted imidazole formate type derivative with a novel structure and belongs to the field of pharmaceutical chemistry. The invention further discloses application of the substituted imidazole formate type derivative to preparation of drugs with calming, hypnosis and/or anesthetic effects and application of the substituted imidazole formatetype derivative to preparation of drugs capable of controlling status epilepticus. The compound disclosed by the invention has a relatively good inhibition effect on a central nervous system and provides a new choice for clinically screening and/or preparing the drugs with the calming, hypnosis and/or anesthetic effects and capable of controlling the status epilepticus. The formula I is shown in the description.

Genetic incorporation of 4-fluorohistidine into peptides enables selective affinity purification

Due to the lowered pKa of 4-fluorohistidine relative to histidine, peptides and proteins containing this amino acid are potentially endowed with novel properties. We report here the optimized synthesis of 4-fluorohistidine and show that it can efficiently replace histidine in in vitro translation reactions. Moreover, peptides containing 6×-fluorohistidine tags are able to be selectively captured and eluted from nickel resin in the presence of his-tagged protein mixtures.

An enantioselective synthesis of (S)-4-fluorohistidine

We report a new synthesis of enantiomerically pure (S)-4-fluorohisitidine based on diastereoselective alkylation of MOM-protected 4-fluoro-5-bromomethyl imidazole using the Sch?llkopf bis-lactim amino acid synthesis. Improvements in procedures for preparation of key intermediates are also described. (S)-4-Fluorohisitidine prepared by this new method was identical in all respects to material prepared by previous procedures.

Prodrugs phosphorus-containing compounds

Prodrugs of formula I, their uses, their intermediates, and their method of manufacture are described:

Photochemistry of Diazonium Salts. 5. Syntheses of 2,4-Difluoroimidazole-5-carboxylic Acid and Related Compounds

Catalytic hydrogenolysis, effective for the synthesis of 2-aminoimidazoles from 2-(arylazo)imidazoles, cannot be used to prepare 2-amino-4-fluoroimidazoles because the fluorine atom is lost simultaneously; formamidinesulfinic acid, however, achieves the required conversion in good yield.Ethyl 2,4-difluoroimidazole-5-carboxylate is obtained by photolysis of ethyl 2-diazonio-4-fluoroimidazole-5-carboxylate in fluoroboric acid.The ester is saponified to the acid in 1 N base (without loss of fluorine) but is stable in 0.05 N base; the ester also resists ammonolysis to the carboxamide or hydride reduction to the carbinol.Ammonolysis of ethyl 2-amino-4-fluoroimidazole-5-carboxylate is successful, however, and the resulting carboxamide is converted, via diazotation and photolysis, into 2,4-difluoroimidazole-5-carboxamide.N-Alkyl derivatives of the difluoro ester undergo facile hydride reduction of the ester function, but only with prior reductive loss of fluorine at C-2.The difluoro acid is stable to diborane reduction over 1 month.These examples of resistance to normal carboxyl modification are ascribed to the facile generation of the imidazolate ion in basic media and a resulting large increase in electron density at the carbonyl carbon by resonance overlap.

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.