119830-06-7

Basic information

• Product Name: L-Glutamic acid, N-[4-(methylamino)benzoyl]-, bis[(2,2-dimethyl-1-oxopropoxy)methyl] ester
• CAS NO: 119830-06-7
• Molecular Formula: C25H36N2O9
• Molecular Weight: 508.569
• Mol File: 119830-06-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Glutamic acid, N-[4-(methylamino)benzoyl]-, bis[(2,2-dimethyl-1-oxopropoxy)methyl] ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid, N-[4-(methylamino)benzoyl]-, bis[(2,2-dimethyl-1-oxopropoxy)methyl] ester(119830-06-7)
• EPA Substance Registry System: L-Glutamic acid, N-[4-(methylamino)benzoyl]-, bis[(2,2-dimethyl-1-oxopropoxy)methyl] ester(119830-06-7)

Safety Data

• Hazardous Substances Data: 119830-06-7(Hazardous Substances Data)

Upstream product

• 875667-98-4 di-tert-butyl N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-L-glutamate 
• 2528-30-5 4-<<(benzyloxy)carbonyl>methylamino>benzoic acid 
• 16874-06-9 di-tert-butyl L-glutamate 
• 53064-79-2 iodomethyl pivaloate 
• 2528-31-6 (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-pentanedioic acid 
• 875667-97-3 (4-azidocarbonyl-phenyl)-methyl-carbamic acid benzyl ester 
• 875668-00-1 bis(pivaloyloxymethyl) N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-L-glutamate 

Relevant articles and documents

Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-γ- [ψP(O)(OH)]-glutarate, a potent inhibitor of folylpoly-γ-glutamate synthetase: Synthesis and hydrolytic stability

Ester prodrugs of the phosphinate pseudopeptide N-[(4-deoxy-4-amino-10- methyl)pteroyl]glutamate-γ-[ψP-(O)(OH)]-glutarate (1a) were synthesized. H-phosphinic acids derived from N-Cbz vinyl glycine esters were converted to the desired pseudopeptides by Michael addition to α-methyleneglutarate esters. Pivaloyloxymethyl (POM) ester moieties were incorporated in both the N-terminal and C-terminal fragments prior to formation of either C-P bond, N-Alkylation of the corresponding amides derived from N-(N-methyl)aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding γ-glutamyl conjugate were also synthesized using the same strategy. All prodrugs were evaluated in Chinese hamster ovary cells. Although the pseudopeptide prodrugs were ineffective, prodrugs of methotrexate and the corresponding γ-glutamyl conjugate were equipotent with the parent compounds. Stability of the prodrugs was investigated in both phosphate buffer and cell line medium to provide a rationale for the observed biological data.