610791-05-4

Basic information

• Product Name: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER
• Synonyms: TERT-BUTYL METHYL AZETIDINE-1,3-DICARBOXYLATE;1-BOC-AZETIDINE-3-CARBOXYLIC ACID METHYL ESTER;AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER;Methyl 1-Boc-azetidine-3-carboxylate;1-tert-butyl 3-methyl azetidine-1,3-dicarboxylate;N-Boc-3-azetidine carboxylic acid methyl ester;Methyl 1-Boc-azetidine-3-...;Methyl azetidine-3-carboxylate, N-BOC protected
• CAS NO: 610791-05-4
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.25
• Product Categories: pharmacetical
• Mol File: 610791-05-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 269°C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.072 g/mL at 25 °C
• Vapor Pressure: 0.00743mmHg at 25°C
• Refractive Index: n20/D1.452
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -2.97±0.40(Predicted)
• CAS DataBase Reference: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(610791-05-4)
• EPA Substance Registry System: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(610791-05-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 610791-05-4(Hazardous Substances Data)

Usage

Uses

Building block used as a precursor to the synthesis of azaspiro[3.4]octanes developed in the Carreira group. This substrate can be readily functionalized via enolization at the 3-position in the presence of LDA.

InChI:InChI=1/C10H17NO4/c1-10(2,3)15-9(13)11-5-7(6-11)8(12)14-4/h7H,5-6H2,1-4H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 343238-58-4 methyl azetidine-3-carboxylate 
• 53871-06-0 1-(diphenylmethyl)-3-methoxycarbonylazetidine 
• 142253-55-2 1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 100202-39-9 methyl 3-azetidinecarboxylate hydrochloride 

Downstream Products

• 1449329-46-7 3-[(2S,4R)-4-(2-chloro-4-methoxy-benzenesulfonyl)-2-(1-cyano-cyclopropylcarbamoyl)-pyrrolidine-1-carbonyl]-3-(5-chloro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester 
• 898228-37-0 3-methyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 
• 1363382-91-5 3-hydroxymethyl-3-methyl-azetidine-1-carboxylic acid tert-butyl ester 
• 1126650-67-6 3-fluoro-3-(hydroxymethyl)azetidin-1-carboxylic acid tert-butyl ester 
• 1363382-00-6 1-tert-butyl 3-methyl 3-fluoroazetidine-1,3-dicarboxylate 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

TARGETING COMPOUNDS

The disclosure provides, at least in part, liver, intestine and/or kidney-targeting compounds and their use in treating liver, intestine and/or kidney disorders, such as non-alcoholic steatohepatitis, alcoholic steatohepatitis, hepatocellular carcinoma, liver cirrhosis, and hepatitis B; and/or chronic kidney disease, glomerular disease such as IGA nephropathy, lupus nephritis, or polycystic kidney disease. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

Polysubstituted-indazole compounds and application of same as IDO inhibitors

The invention discloses polysubstituted-indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application of the compounds as IDO inhibitors. The compounds provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections related to cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.