71869-80-2

Basic information

• Product Name: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl
• Synonyms: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl;(R)-(Tetrahydro-2,6-dioxo-2H-pyran-3-yl)-carbaMic Acid PhenylMethyl Ester
• CAS NO: 71869-80-2
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.24602
• Product Categories: Amino Acids & Derivatives;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 71869-80-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Glacial Acetone
• CAS DataBase Reference: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl(CAS DataBase Reference)
• NIST Chemistry Reference: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl(71869-80-2)
• EPA Substance Registry System: [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl(71869-80-2)

Safety Data

• Hazardous Substances Data: 71869-80-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

[(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbaMic Acid PhenylMethyl is used in the synthesis of Cbz-aminoglutarimides and Cbz-succinimides, for their anticonvulsant activity.

Upstream product

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

Downstream Products

• 123628-68-2 Z-D-Glu-ol 
• 65706-99-2 1-benzyl N-carbobenzoxy-L-glutamate 
• 911207-20-0 C₁₇H₂₀N₂O₇ 
• 756479-51-3 C₁₃H₁₄N₂O₅ 
• 110547-98-3 N-(benzyloxycarbonyl)-cyclo(D-glutamyl-D-lysyl) methyl ester 

Relevant articles and documents

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.

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.