642411-11-8

Basic information

• Product Name: Diethyl 1-benzylazetidine...
• Synonyms: Diethyl 1-benzylazetidine...;Diethyl 1-benzylazetidine-3,3-dicarboxylate;3,3-Azetidinedicarboxylic acid, 1-(phenylMethyl)-, diethyl ester;3,3-diethyl 1-benzylazetidine-3,3-dicarboxylate;diethyl 1-(phenylmethyl)-3,3-azetidinedicarboxylate
• CAS NO: 642411-11-8
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 203
• Mol File: 642411-11-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Diethyl 1-benzylazetidine...(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 1-benzylazetidine...(642411-11-8)
• EPA Substance Registry System: Diethyl 1-benzylazetidine...(642411-11-8)

Safety Data

• Hazardous Substances Data: 642411-11-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
Diethyl 1-benzylazetidine-2,2-dicarboxylate is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs that can address unmet medical needs or improve upon existing treatments.
Used in Organic Synthesis:
In the field of organic synthesis, Diethyl 1-benzylazetidine-2,2-dicarboxylate serves as a versatile building block. It is used to construct complex organic molecules that may have applications across different industries, including but not limited to materials science, agrochemicals, and specialty chemicals.
Used in Drug Discovery:
Diethyl 1-benzylazetidine... is employed in drug discovery processes to explore its potential in creating new molecular entities. Its reactivity and structural features make it a candidate for further chemical modifications that could lead to the development of innovative therapeutic agents.
Used in Chemical Research:
Diethyl 1-benzylazetidine-2,2-dicarboxylate is also used in academic and industrial research settings to study its chemical properties and to understand its behavior in various reaction conditions. This research can lead to new insights and methodologies in organic chemistry.

Upstream product

• 20605-01-0 diethyl bis(hydroxymethyl)malonate 
• 100-46-9 benzylamine 
• 105-53-3 diethyl malonate 
• 642411-10-7 diethyl 2,2-bis((((trifluoromethyl)sulfonyl)oxy)methyl)malonate 

Downstream Products

• 1011479-75-6 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate 
• 1078166-50-3 ethyl 1-benzyl-3-(hydroxymethyl)azetidine-3-carboxylate 
• 1016233-34-3 1-[(7-benzyloxymethyl-4-tert-butoxy-9-deazapurin-9-yl)methyl]azetidine-3,3-dimethanol 
• 1016232-92-0 azetidine-3,3-dimethanol hydrochloride 
• 1016233-08-1 3,3-bis(hydroxymethyl)azetidine-1-carboxylic acid tert-butyl ester 
• 26096-30-0 N-benzyl-3,3-bis-(hydroxymethyl)-azetidine 
• 103491-30-1 ethyl 1-benzylazetidine-3-carboxylate 

Relevant articles and documents

ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF

A compound of Formula (I) or or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating hearing loss or balance disorder: Formula (I) wherein R1 and Y are as defined herein.

FUSED HETEROCYCLIC COMPOUNDS AS PROTEIN KINASE INHIBITORS

The invention is fused heterocyclic compounds of formula (I), and salts thereof, compositions thereof, and methods of use therefor. In particular, disclosed herein are certain fused heterocyclic compounds that can be useful for inhibiting protein kinase, including Bruton’ s tyrosine kinase (Btk), and for treating disorders mediated thereby.

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.

Design, synthesis and biological evaluation of palladium (II) complexes with 1-(substituted benzyl) azetidine-3,3-dicarboxylates as leaving group

A series of palladium complexes with 2,2′-bipyridine and 1-(substituted benzyl) azetidine-3, 3-dicarboxylates as ligands were synthesized and characterized by IR, 1H-NMR, ESI-MS spectra and elemental analysis. The in vitro cytotoxicity assays were carried out against A549, HCT-116, HepG-2 and SGC7901 cancer cell lines. The result showed that most of the complexes possessed moderate antiproliferative activity against HCT-116, HepG-2 and SGC7901 cell lines. Complex 12 (with 2,2′-bipyridine and 1-(3-methoxylbenzyl)azetidine-3,3-dicarboxylate as ligand) was the most potent antitumor agent among all thirteen complexes, which showed comparable or better cytotoxicity against all four tested cancer cell lines than carboplatin. The interaction between complex 12 and pET22b plasmid DNA was investigated by agarose gel electrophoresis, and the result of the study showed that complex 12 had no obvious interaction with the plasmid DNA.

FUSED HETEROCYCLIC COMPOUNDS AS PROTEIN KINASE INHIBITORS

The invention is fused heterocyclic compounds of formula (I), and salts thereof, compositions thereof, and methods of use therefor. In particular, disclosed herein are certain fused heterocyclic compounds that can be useful for inhibiting protein kinase, including Bruton's tyrosine kinase (Btk), and for treating disorders mediated thereby.

Synthesis, antiproliferative activity and DNA binding study of mixed ammine/cyclohexylamine platinum(II) complexes with 1-(substituted benzyl) azetidine-3, 3-dicarboxylates

A novel series of ammine/cyclohexylamine platinum(II) complexes with 1-(substituted benzyl) azetidine-3, 3-dicarboxylates as leaving groups have been synthesized and characterized. All complexes were characterized by elemental analysis, IR, 1H NMR, and ESI-MS spectra. The in vitro antiproliferative activities of the platinum-based compounds have been investigated against several human cancer cell lines, indicating that complexes 1 and 11 showed comparable cytotoxicity to those of cisplatin and oxaliplatin against four cell lines, superior to that of carboplatin. The results of drug safety evaluation (acute toxicity study) showed that complex 11 was much less toxic than cisplatin and oxaliplatin. Flow cytometry and agarose gel electrophoresis studies revealed that both complexes 1 and 11 induced apoptosis of tumor cells and demonstrated the binding affinity of complexes with pET22b plasmid DNA.

PROCESS FOR MAKING AZETIDINE-3-CARBOXYLIC ACID

The present invention is directed to an improved process for synthesizing azetidine-3-carboxylic acid, comprising triflating diethylbis(hydroxymethyl)malonate followed by azetidine ring-formation by intramolecular cyclization using an amine, decarboxylation to give the mono acid azetidine and hydrogenation to give the title compound. Azetidine-3-carboxylic acid is useful as an intermediate for making certain S1P?1#191/Edg1 receptor agonists, which are immunosupressive agents.

A practical process for the preparation of azetidine-3-carboxylic acid

A practical and convenient synthesis of azetidine-3-carboxylic acid (1) that proceeded in 55% overall yield from commercially available diethylbis(hydroxymethyl)malonate (3) is reported. Azetidine ring-formation was achieved in high yield by cyclization of bistrifiate of the diol (3) and benzylamine. Decarboxylation under carefully pH-controlled conditions gave the mono acid azetidine that was hydrogenated to give the title compound.