107521-99-3

Usage

Structure

Cyclohexane carboxylic acid derivative with a benzoylamino group attached to the cyclohexane ring

Functional groups

Carboxylic acid, benzoylamino

Applications

a. Organic synthesis reactions
b. Pharmaceutical properties
c. Building block for other chemical compounds

Potential as a drug target

Treatment of various diseases

Significance

Pharmaceutical and chemical applications

Upstream product

• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 98-88-4 benzoyl chloride 
• 932-89-8 2-cyclohexylidene ethanol 
• 108-94-1 cyclohexanone 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 3253-43-8 Spiro<4.5>decan-2,4'-oxazolidine-2,5'-dione 
• 100-58-3 phenylmagnesium bromide 
• 17191-43-4 1-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid 
• 115951-16-1 1-tert-butoxycarbonylaminocyclohexanecarboxylic acid 

Downstream Products

• 100722-71-2 1-benzoylamino-cyclohexanecarboxylic acid amide 
• 1016803-54-5 1-(2-methoxybenzamido)cyclohexane-1-carboxylic acid 
• 1154050-60-8 methyl N-(1-(benzamido)cyclohexanecarbonyl)-L-leucine 

Relevant academic research and scientific papers

Palladium-Catalyzed Ortho-Alkoxylation of N-Benzoyl α-Amino Acid Derivatives at Room Temperature

An efficient palladium-catalyzed ortho-alkoxylation of N-benzoyl α-amino acid derivatives at room temperature has been explored. This novel transformation, using amino acids as directing groups, Pd(OAc)2 as catalyst, alcohols as the alkoxylation reagents, and PhI(OAc)2 as the oxidant, showed wide generality, good functional tolerance, and high monoselectivity and regioselectivity.

The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement

An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.

Synthesis of sterically hindered N-acylated amino acids from N-carboxyanhydrides

Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.

Cycloalkylcarbonylamino Acid Derivative and Process For Producing The Same

Cycloalkylcarbonylamino acid derivatives, which are raw material intermediates of a novel cycloalkane carboxamide derivative that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbonylamino acid derivative r

Cycloalkylcarbonylamino Acid Ester Derivative and Process for Producing The Same

Cycloalkylcarbonylamino acid ester derivatives, which are raw material intermediates for a novel cycloalkane carboxamide derivative having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbony

Catalytic, one-pot synthesis of β-amino acids from α-amino acids. Preparation of α,β-peptide derivatives

(Chemical Equation Presented) The one-pot conversion of readily available α-amino acid into β-amino acid derivatives was carried out in good yields. The method is a sequential process initiated by a tandem radical decarboxylation-oxidation reaction; the resulting acyliminium ion was trapped by silyl ketenes. Stoichiometric and catalytic versions of this reaction were developed and then applied to prepare modified di- and tripeptides. Interestingly, some tripeptides formed expanded β-turns in the solid state.

OXAZOLONE DERIVATIVE

Novel raw material compounds are provided that are useful for producing novel cycloalkane carboxamide derivatives having cathepsin K inhibitory action. An oxazolone derivative represented by formula (I): [wherein, R1 represents a substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted phenyl group, substituted or unsubstituted naphthyl group or substituted or unsubstituted heterocyclic group, and ring A represents a saturated cyclic alkylidene group having 6 to 7 carbon atoms].

CYCLOALKANECARBOXAMIDE DERIVATIVE AND METHOD FOR PRODUCING SAME

Novel cycloalkane carboxamide derivatives having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkane carboxamide derivative represented by the following general formula (I), or a pharmaceutically acceptable salt thereof: (wherein R1 and R2 represent (substituted) alkyl groups, (substituted) alkenyl groups, (substituted) alkynyl groups, (substituted) aromatic hydrocarbon groups or (substituted) heterocyclic groups, ring A represents an alkylidene group having 5 to 7 carbon atoms, and ring B represents a formyl group or a hydroxymethyl group).