192725-87-4

Basic information

• Product Name: N-(3-PropanaMido)-L-valine tert-Butyl Ester
• Synonyms: N-(3-PropanaMido)-L-valine tert-Butyl Ester;N-(3-AMino-3-oxopropyl)-L-valine 1,1-DiMethylethyl Ester
• CAS NO: 192725-87-4
• Molecular Formula: C₁₂H₂₄N₂O₃
• Molecular Weight: 244.33056
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 192725-87-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: N-(3-PropanaMido)-L-valine tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-PropanaMido)-L-valine tert-Butyl Ester(192725-87-4)
• EPA Substance Registry System: N-(3-PropanaMido)-L-valine tert-Butyl Ester(192725-87-4)

Safety Data

• Hazardous Substances Data: 192725-87-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Upstream product

• 192725-86-3 N-(2-carbomethoxy)ethyl-L-valine t-butyl ester 
• 13211-31-9 tert-butyl L-valinate 
• 13518-40-6 L-valine tert-butylester hydrochloride 
• 79-06-1 2-propenamide 

Downstream Products

• 221553-72-6 (S)-N-{(1S,3S,4S)-1-Benzyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-2-(4-hydroxy-2-oxo-tetrahydro-pyrimidin-1-yl)-3-methyl-butyramide 
• 192725-39-6 4-Oxo-ABT-378 

Relevant articles and documents

Discovery of imidazolidine-2,4-dione-linked HIV protease inhibitors with activity against lopinavir-resistant mutant HIV

A new series of HIV protease inhibitors has been designed and synthesized based on the combination of the (R)-(hydroxyethylamino)sulfonamide isostere and the cyclic urea component of lopinavir. The series was optimized by replacing the 6-membered cyclic urea linker with an imidazolidine-2,4-dione which readily underwent N-alkylation to incorporate various methylene-linked heterocycle groups that bind favorably in site 3 of HIV protease. Significant improvements compared to lopinavir were seen in cell culture activity versus wild-type virus (pNL4-3) and the lopinavir-resistant mutant virus A17 (generated by in vitro serial passage of HIV-1 (pNL4-3) in MT-4 cells). Select imidazolidine-2,4-dione containing PIs were also more effective at inhibiting highly resistant patient isolates Pt1 and Pt2 than lopinavir. Pharmacokinetic data collected for compounds in this series varied considerably when coadministered orally in the rat with an equal amount of ritonavir (5 mg/kg each). The AUC values ranged from 0.144 to 12.33 μg h/mL.

Synthesis and antiviral activities of the major metabolites of the HIV protease inhibitor ABT-378 (Lopinavir)

The HIV protease inhibitor ABT-378 (Lopinavir) is metabolized rapidly and extensively by CYP-3A4 catalyzed oxidation. Three of the major metabolites identified were synthesized and their antiviral (HIV) activities determined.