142253-56-3

Usage

Chemical Properties

Clear colorless liquid

Uses

It is an intermediate in organic syntheses

Upstream product

• 142253-55-2 1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid 
• 543-27-1 isobutyl chloroformate 
• 928038-44-2 3-(hydroxymethyl)azetidine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50-00-0 formaldehyd 
• 254454-54-1 tert-butyl-3-iodoazetidine-1-carboxylate 
• 95849-02-8 3-hydroxymethyl-1-azetidine 
• 141699-55-0 tert-butyl 3-hydroxyazetidine-1-carboxylate 
• 934664-41-2 3-methylene-azetidine-1-carboxylic acid tert-butyl ester 
• 398489-26-4 tert-butyl 3-oxoazetidine-1-carboxylate 
• 72351-36-1 1-diphenylmethyl-3-hydroxymethylazetidine 
• 541-41-3 chloroformic acid ethyl ester 
• 610791-05-4 azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 

Downstream Products

• 177947-96-5 tert-butyl 3-formylazetidine-1-carboxylate 
• 892408-34-3 3-(3-formyl-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester 
• 920284-87-3 3-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester 
• 942308-05-6 3-methoxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 1217417-34-9 tert-butyl 3-{[2-({(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}carbamoyl)-4-(trifluoromethyl)phenoxy]methyl}azetidine-1-carboxylate 
• 1332301-15-1 tert-butyl 3-(phenoxymethyl)azetidine-1-carboxylate 
• 1374342-02-5 C₃₄H₃₄ClF₃N₄O₅ 
• 1236007-18-3 tert-butyl 3-(mercaptomethyl)azetidine-1-carboxylate 
• 1398705-08-2 tert-butyl-3-[(3,4-difluorophenyl)(hydroxy)methyl]azetidine-1-carboxylate 
• 1398705-07-1 C₁₅H₁₉ClFNO₃ 

Relevant academic research and scientific papers

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

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.

Condensed tricyclic compound and applications in medicines

The invention relates to a condensed tricyclic compound and applications in medicines, particularly to applications of the condensed tricyclic compound as drugs for treating and/or preventing hepatitis B, specifically to a compound represented by general

Design and synthesis of cyanamides as potent and selective N-acylethanolamine acid amidase inhibitors

N-acylethanolamine acid amidase (NAAA) inhibition represents an exciting novel approach to treat inflammation and pain. NAAA is a cysteine amidase which preferentially hydrolyzes the endogenous biolipids palmitoylethanolamide (PEA) and oleoylethanolamide (OEA). PEA is an endogenous agonist of the nuclear peroxisome proliferator-activated receptor-α (PPAR-α), which is a key regulator of inflammation and pain. Thus, blocking the degradation of PEA with NAAA inhibitors results in augmentation of the PEA/PPAR-α signaling pathway and regulation of inflammatory and pain processes. We have prepared a new series of NAAA inhibitors exploring the azetidine-nitrile (cyanamide) pharmacophore that led to the discovery of highly potent and selective compounds. Key analogs demonstrated single-digit nanomolar potency for hNAAA and showed >100-fold selectivity against serine hydrolases FAAH, MGL and ABHD6, and cysteine protease cathepsin K. Additionally, we have identified potent and selective dual NAAA-FAAH inhibitors to investigate a potential synergism between two distinct anti-inflammatory molecular pathways, the PEA/PPAR-α anti-inflammatory signaling pathway,1–4 and the cannabinoid receptors CB1 and CB2 pathways which are known for their antiinflammatory and antinociceptive properties.5–8 Our ligand design strategy followed a traditional structure–activity relationship (SAR) approach and was supported by molecular modeling studies of reported X-ray structures of hNAAA. Several inhibitors were evaluated in stability assays and demonstrated very good plasma stability (t1/2 > 2 h; human and rodents). The disclosed cyanamides represent promising new pharmacological tools to investigate the potential role of NAAA inhibitors and dual NAAA-FAAH inhibitors as therapeutic agents for the treatment of inflammation and pain.

IRAK4 INHIBITORS AND USES THEREOF

Compounds of Formula I as IRAK4 inhibitors are disclosed. The pharmaceutical compositions comprising compounds of formula I, methods of synthesis of these compounds, methods of treatment for diseases associated with IRAK-4 such as inflammatory diseases an

Facile synthesis of 2-azaspiro[3.4]octane

Our annulation strategy utilized for the synthesis of 2-azaspiro[3.4]octane is explained. Three successful routes for the synthesis were developed. One of the approaches involved annulation of the cyclopentane ring and the remaining two approaches involved annulation of the four membered ring. All three approaches employ readily available starting materials with conventional chemical transformations and minimal chromatographic purifications to afford the title compound. The merits and limitations of the three approaches are also discussed.

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

The synthesis of benzosultams has been achieved through a gold(I)-catalyzed ammonium formation strategy. Starting from easily available N-(2-alkynyl)phenylsulfonyl azetidine derivatives, a cyclization reaction generated a spiroammonium gold intermediate t

PROCESS FOR THE PREPARATION OF 2-(3-(FLUOROMETHYL)AZETIDIN-1-YL)ETHAN-1-OL

Methods of making 2-(3-(fluoromethyl)azetidin-1-yl)ethan-1-ol 9, an intermediate useful for the synthesis of estrogen receptor modulating compounds are described.

REDUCTION OF PRO-INFLAMMATORY HDL USING A LEUKOTRIENE INHIBITOR

A method involving the administration of a therapeutically effective amount of a leukotriene inhibitor, a pharmaceutically acceptable salt, a pharmaceutically acceptable N-oxide, a pharmaceutically active metabolite, a pharmaceutically acceptable prodrug, or pharmaceutically acceptable solvate thereof to a human for reducing a level of pro-inflammatory HDL in the human. Various examples of leukotriene inhibitors, including 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin- 3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2, 2-dimethyl-propionic acid, are disclosed for administration for the reduction of pro-inflammatory HDL in a human. Reduction of pro-inflammatory HDL by the leukotriene inhibitor may include conversion of at least a portion of pro-inflammatory HDL to anti-inflammatory HDL.

Pleuromutilin antibiotics

The present invention relates to pleuromutilin antibiotics represented by a general formula (I), pharmaceutically acceptable salts, prodrugs, solvates or stereoisomers thereof, wherein R, R, R, R, m, X and Y are defined in an instruction. The present invention further relates to preparation methods of the compounds, drug compositions containing the compounds, drug preparations containing the compounds, and applications of the compounds in preparation of drugs for treatment and/or prevention of diseases caused by microorganisms.