82938-50-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID is used as a building block for the synthesis of pharmaceuticals, leveraging its azetidin-2-one core and carboxylic acid functionality to create diverse medicinal compounds.
Used in Organic Synthesis:
In the realm of organic synthesis, (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID is utilized as a key intermediate, taking advantage of its TBS protecting group to facilitate selective reactions and the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
(4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID is employed as a structural component in medicinal chemistry, potentially contributing to the development of new drugs through its unique arrangement of functional groups and its ability to be modified in various ways for different therapeutic targets.
Used in Drug Development:
In the drug development industry, (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID is used as a precursor in the design and synthesis of novel drug candidates, capitalizing on its reactivity and the versatility of its functional groups to create potential therapeutic agents.

InChI:InChI=1/C10H19NO3Si/c1-10(2,3)15(4,5)11-7(9(13)14)6-8(11)12/h7H,6H2,1-5H3,(H,13,14)/t7-/m0/s1

Upstream product

• 130540-09-9 dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 82938-49-6 benzyl (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 
• 185387-26-2 (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 

Downstream Products

• 256418-85-6 (3S,4R)-3-benzyl-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid 
• 158419-31-9 menthyl N-<1-tert-butyldimethylsilyl-2-azetidinone-4-carboxy>glycinate 
• 169061-45-4 (3R,4S)-3-(2'-hydroxyethyl)azetidin-2-one-4-carboxylic acid 
• 103700-11-4 (2S,3R)-1-t-butyldimethylsilyl-3-benzyl-4-oxo-2-azetidinecarboxylic acid 
• 357429-20-0 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester 
• 357429-14-2 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(ω-nitro)arginyl}-L-valine benzyl ester 
• 357429-17-5 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)tyrosyl}-L-isoleucine benzyl ester 
• 357429-22-2 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester 
• 236123-21-0 benzyl [(S)-1-[N-(tert-butyldimethylsilyl)-4-oxo-azetidine-2-carbonyl]amino]-cyclopropanecarboxylate 
• 926630-08-2 C₃₃H₃₆N₂O₄Si 
• 140844-47-9 (S)-4-[2-Benzenesulfonyl-2-(pyridin-2-ylsulfanyl)-propyl]-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one 
• 140844-27-5 (S)-4-[2-Benzenesulfonyl-2-(pyridin-2-ylsulfanyl)-ethyl]-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one 

Relevant academic research and scientific papers

QUATERNARY LACTAM COMPOUND AND PHARMACEUTICAL USE THEREOF

A quaternary lactam compound of formula (I). The compound is used in the manufacture of a medicament for the treatment and/or prevention of thrombotic or thromboembolic disorders.

The discovery and optimization of benzimidazoles as selective NaV1.8 blockers for the treatment of pain

The voltage gated sodium channel NaV1.8 has been postulated to play a key role in the transmission of pain signals. Core hopping from our previously reported phenylimidazole leads has allowed the identification of a novel series of benzimidazole NaV1.8 blockers. Subsequent optimization allowed the identification of compound 9, PF-06305591, as a potent, highly selective blocker with an excellent preclinical in vitro ADME and safety profile.

Stereoselective Synthesis of Tricyclic Diproline Analogues that Mimic a PPII Helix: Structural Consequences of Ring-Size Variation

Polycyclic proline-derived scaffolds (ProMs) have recently demonstrated their value as conformationally defined dipeptide analogs for the modular construction of secondary structure mimetics, specifically interfering with PPII helix-mediated protein-protein interactions. We disclose the stereoselective synthesis of two new tricyclic amino acid scaffolds (ProM-4 and ProM-8) that differ from the first generation scaffold ProM-1 by the size of ring A. Conformational preferences and subtle structural differences of the three homologous scaffolds were analyzed by X-ray crystallography, computational calculations, and NMR spectroscopy. N-tert-butoxycarbonyl(Boc)-3-(1-propenyl)azetidine-2-carboxylic acid was prepared from L-aspartic acid through β-lactam intermediates. The corresponding piperidine-based building block rac-N-Boc-3-vinylpipecolic acid was synthesized by Cu-catalyzed 1,4-addition of vinyl-MgBr to methyl N-Boc-2,3-dehydropipecolate. Target molecules were prepared through peptide coupling of the respective ring A building blocks with cis-5-vinylproline tert-butyl ester and subsequent ring-closing metathesis. Selective deprotection of a tert-butyl carbamate (N-Boc protecting group) in the presence of a tert-butyl ester was achieved with trifluoroacetic acid at 0 C. Two new tricyclic amino acid scaffolds, which differ from the first generation scaffold by the size of ring A, were stereoselectively synthesized. The conformational analysis of the three homologous scaffolds was revealed by NMR spectroscopy.

Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

β-Lactam derivatives as enzyme inhibitors: N-substituted derivatives of (S)-4-oxoazetidine-2-carboxylate as inhibitors of elastase and papain

N-Alkyl and N-acyl substituted 4-oxoazetidine-2-carboxylates are synthesized and evaluated as inhibitors of the proteases porcine pancreatic elastase (PPE) and papain. The compounds are obtained by alkylation or acylation at the nitrogen of benzyl (S)-4-oxoazetidine-2-carboxylate, which is synthesized by a modified literature procedure. The enzymatic assays prove some derivatives to be effective inhibitors of PPE and/or papain. The N-BOC protected amino acid derivatives 10 and 13 inhibit PPE reversibly with K(I)-values in the micromolar range. On the other hand, papain is inactivated irreversibly by benzyl (S)-2-(benzyloxycarbonyl)azetidin-1-acetate (6).

Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: Effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice

Analogs of A-98593 (1) and its enantiomer ABT-594 (2) with diverse substituents on the pyridine ring were prepared and tested for affinity to nicotinic acetylcholine receptor binding sites in rat brain and for analgesic activity in the mouse hot plate assay. Numerous types of modifications were consistent with high affinity for [3H]cytisine binding sites. By contrast, only selected modifications resulted in retention of analgesic potency in the ame range as 1 and 2. Analogs of 2 with one or two methyl substituents at the 3-position of the azetidine ring also were prepared and found to be substantially less active in both assays.

Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.

Studies on the Alkylation of Dipeptide Substrates

Alkylation of anions derived from dipeptides with a glycine at the C-terminus have been investigated.A hydrocarbon sedition in the N-terminal residue does impart some asymmetric induction.The use of a chiral ester derivative provides the potential for double asymmetric induction and good selectivity.With an aspartyl residue at the N-terminus, problems were encountered due to competing side reactions.The use of an azetidione could circumvent some of these, but the observed induction was not high.

STEREOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN

The first synthesis of the novel α-amino acid dealanylalahopcin starting from (L)-aspartic acid is described.