71869-80-2

Usage

Uses

Used in Pharmaceutical Industry:
[(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl is used as a key intermediate in the synthesis of Cbz-aminoglutarimides and Cbz-succinimides for their anticonvulsant activity. These synthesized compounds have the potential to be developed into effective treatments for seizure disorders and other related neurological conditions.
Chemical Properties:
[(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl is characterized as a white solid, which is an important physical property for its handling, storage, and use in chemical reactions.

Upstream product

• 63648-73-7 N-benzyloxycarbonyl-D-glutamic acid 
• 6893-26-1 D-Glutamic acid 
• 501-53-1 benzyl chloroformate 
• 56-86-0 L-glutamic acid 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 

Downstream Products

• 97975-51-4 N-[1-(N-carbobenzoxy-γ-D-glutamyl)-3,4-dimethoxyphenyl]glycine 
• 110473-28-4 N-(benzyloxycarbonyl)-D-glutamyl-N'-(tert-butyloxycarbonyl)-D-lysine methyl ester 
• 97975-31-0 1-(N-carbobenzoxy-γ-D-glutamyl)indoline-2(S)-carboxylic acid 
• 97975-49-0 1-(N-carbobenzoxy-γ-D-glutamyl)-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylic acid 
• 97975-50-3 1-(N-carbobenzoxy-γ-D-glutamyl)proline 
• 97975-56-9 3-pyridylmethyl 1-(N-carbobenzoxy-γ-D-glutamyl)indoline-2(S)-carboxylate 
• 97975-52-5 (R)-2-Benzyloxycarbonylamino-4-(carboxymethyl-cyclopentyl-carbamoyl)-butyric acid 
• 97975-46-7 1-(N-carbobenzoxy-γ-D-glutamyl)-cis-perhydroindoline-2(S)-carboxylic acid 
• 97975-48-9 1-(N-carbobenzoxy-γ-D-glutamyl)-cis-octahydroisoquinoline-3(S)-carboxylic acid 
• 97975-47-8 1-(N-carbobenzoxy-γ-D-glutamyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 65706-99-2 1-benzyl N-carbobenzoxy-L-glutamate 
• 911207-20-0 C₁₇H₂₀N₂O₇ 
• 756479-51-3 C₁₃H₁₄N₂O₅ 

Relevant academic research and scientific papers

Rational Drug Design of Topically Administered Caspase 1 Inhibitors for the Treatment of Inflammatory Acne

The use of an interleukin β antibody is currently being investigated in the clinic for the treatment of acne, a dermatological disorder affecting 650M persons globally. Inhibiting the protease responsible for the cleavage of inactive pro-IL1β into active IL-1β, caspase-1, could be an alternative small molecule approach. This report describes the discovery of uracil 20, a potent (38 nM in THP1 cells assay) caspase-1 inhibitor for the topical treatment of inflammatory acne. The uracil series was designed according to a published caspase-1 pharmacophore model involving a reactive warhead in P1 for covalent reversible inhibition and an aryl moiety in P4 for selectivity against the apoptotic caspases. Reversibility was assessed in an enzymatic dilution assay or by using different substrate concentrations. In addition to classical structure-activity-relationship exploration, topical administration challenges such as phototoxicity, organic and aqueous solubility, chemical stability in solution, and skin metabolic stability are discussed and successfully resolved.

An expedient synthesis of non-racemic N-alkylated pyrrolidin-2,5-diones and piperidin-2,6-diones as peptidomimetics

In our hands, access to 2 novel peptidomimetic scaffolds, based on N-alkylated pyrroldin-2,5-diones and piperidin-2,6-diones, proved to be much more challenging than anticipated. In this short communication, we disclose the strategies that we explored and

Synthesis and anticonvulsant activity of (R)- and (S)-3-(Carbobenzyloxy- amino-1-glutarimidooxy)esters

A series of (R)- and (S)-3-carbobenzyloxy-amino-1-glutarimidooxy-esters (5a-e) ((R)-and (S)-methyl-1-(3-carbobenzyloxy-amino-I glutarimidooxy)acetate (5a), (R)-and (S)-ethyl-1-(3-carbobenzyloxy-amino-glutarimidooxy)acetate (5b), (R)- and (S)-ethyl-1-(3-carbo-benzyloxy-amino-glutarimidooxy)propionate (5c), (R)- and (S)-methyl-2-(3-carbobenzyloxy-amino-glutarimidooxy)butyrate (5d), (R)- and (S)-ethyl-2-(3-carbobenzyloxy-amino-glutarimidooxy)butyrate (5e) were synthesized and investigated their anticonvulsant activities.

Synthesis of a Novel Class of Peptides: Dilactam-Bridged Tetrapeptides

As model compounds for the study of constrained peptides, the following lactam-bridged derivatives were synthesized: Ac-L--D--NHMe (I), Ac-L--L--NHMe (II), Ac-L--NHMe (III), Ac-L--D--NHMe (IV), Ac-L--L--NHMe (V), and Ac-L--NHMe (VI).Benzyloxycarbonyl and tert-butyloxycarbonyl groups were employed for amine protection and the benzyl and methyl esters for carboxyl protection.Coupling reactions were carried out by the use of active esters or through azide activation.Cyclization reactions were carried out by adding the active ester hydrochlorides into large volumes of pyridine at elevated temperatures.The cyclic intermediates were obtained in yields of 45-50percent.Fragment condensation of the cyclic dipeptides yielded the corresponding dilactam-bridged tetrapeptides.