ArticleJournal of medicinal chemistry2006
Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-gamma-[psiP(O)(OH)]-glutarate, a potent inhibitor of folylpoly-gamma-glutamate synthetase: synthesis and hydrolytic stability.
Article in Journal of medicinal chemistry, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Chemodivergent Synthesis of β‑Phosphonyl Carboxylic Acids and Acylphosphine Oxides via Ring-Opening Addition of Cyclopropenone.Precision chemistry · 2026Article
- A Novel Curcumin-Mycophenolic Acid Conjugate Inhibited Hyperproliferation of Tumor Necrosis Factor-Alpha-Induced Human Keratinocyte Cells.Pharmaceutics · 2021Article
- A Carbomethoxylated Polyvalerolactone from Malic Acid: Synthesis and Divergent Chemical Recycling.ACS macro letters · 2018Article
- UV-mediated hydrophosphinylation of unactivated alkenes with phosphinates under batch and flow conditions.RSC advances · 2018Article
- A Bacterial Cell Shape-Determining Inhibitor.ACS chemical biology · 2016Article
- A multivalent approach of imaging probe design to overcome an endogenous anion binding competition for noninvasive assessment of prostate specific membrane antigen.Molecular pharmaceutics · 2013Article
- Phosphinic acid-based inhibitors of tubulin polyglutamylases.Bioorganic & medicinal chemistry letters · 2013Article
- Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.The Journal of organic chemistry · 2011Article
- Total syntheses of isodomoic acids G and H.Journal of the American Chemical Society · 2009Article
- Inhibition of human folylpolyglutamate synthetase by diastereomeric phosphinic acid mimics of the tetrahedral intermediate.Archives of biochemistry and biophysics · 2009Article
- ATP-dependent ligases in trypanothione biosynthesis--kinetics of catalysis and inhibition by phosphinic acid pseudopeptides.The FEBS journal · 2008Article
- Recent Developments in the Addition of Phosphinylidene-Containing Compounds to Unactivated Unsaturated Hydrocarbons: Phosphorus-Carbon Bond-Formation via Hydrophosphinylation and Related Processes.European journal of organic chemistry · 2008Article
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2 authors.
Funding
Abstract
Ester prodrugs of the phosphinate pseudopeptide N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-gamma-[psiP(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 alpha-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 p-(N-methyl)aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding gamma-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 gamma-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.
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