Synthesis and in vitro biological activity of new deaza analogues of folic acid, aminopterin, and methotrexate with an L-ornithine side chain.

No abstract is available for this paper.

• Publication year

  1991

• Venue

  Journal of Medicinal Chemistry

• Publication date

  1991-04-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JM00108A032PMID 2016722
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogues.

  1989cited by this paper
• The 2-desamino and 2-desamino-2-methyl analogues of aminopterin do not inhibit dihydrofolate reductase but are potently toxic to tumor cells in culture.

  1989cited by this paper
• Inhibition of mammalian folylpolyglutamate synthetase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin bearing a terminal L-ornithine.

  1989cited by this paper
• Methotrexate analogues. 32. Chain extension, alpha-carboxyl deletion, and gamma-carboxyl replacement by sulfonate and phosphonate: effect on enzyme binding and cell-growth inhibition.

  1988cited by this paper
• Methotrexate analogues. 34. Replacement of the glutamate moiety in methotrexate and aminopterin by long-chain 2-aminoalkanedioic acids.

  1988cited by this paper
• Methotrexate analogues. 33. N delta-acyl-N alpha-(4-amino-4-deoxypteroyl)-L-ornithine derivatives: synthesis and in vitro antitumor activity.

  1988cited by this paper
• Mammalian folylpoly-gamma-glutamate synthetase. 3. Specificity for folate analogues.

  1987cited by this paper
• Inhibition of human liver folylpolyglutamate synthetase by non-gamma-glutamylatable antifolate analogs.

  1987cited by this paper
• Methotrexate analogues-27. Dual inhibition of dihydrofolate reductase and folylpolyglutamate synthetase by methotrexate and aminopterin analogues with a gamma-phosphonate group in the side chain.

  1986cited by this paper
• Syntheses and antifolate activity of 5-methyl-5-deaza analogues of aminopterin, methotrexate, folic acid, and N10-methylfolic acid.

  1986cited by this paper
• Folylpolyglutamate synthetase inhibition and cytotoxic effects of methotrexate analogs containing 2,omega-diaminoalkanoic acids.

  1986cited by this paper
• Methotrexate analogues. 26. Inhibition of dihydrofolate reductase and folylpolyglutamate synthetase activity and in vitro tumor cell growth by methotrexate and aminopterin analogues containing a basic amino acid side chain.

  1986cited by this paper
• Syntheses and evaluation as antifolates of MTX analogues derived from 2, omega-diaminoalkanoic acids.

  1985cited by this paper
• Methotrexate analogues. 19. Replacement of the glutamate side chain in classical antifolates by L-homocysteic acid and L-cysteic acid: effect on enzyme inhibition and antitumor activity.

  1984cited by this paper
• Purification and characterization of dihydrofolate reductase from methotrexate-resistant human lymphoblastoid cells.

  1983cited by this paper
• Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.

  1983cited by this paper
• Methotrexate analogues. 14. Synthesis of new gamma-substituted derivatives as dihydrofolate reductase inhibitors and potential anticancer agents.

  1981cited by this paper
• Quinazoline analogues of folic acid.

  1970cited by this paper
• The synthesis of some dipeptides related to gramicidin S.

  1948cited by this paper

• Synthesis and Biological Properties of Ferrocenyl and Organic Methotrexate Derivatives

  2024cites this paper
• A novel access to pyrido[4,3-d]pyrimidine scaffold via Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(β-azidoalkyl)-1,2,3,4-tetrahydropyrimidin-2-ones

  2014cites this paper
• A new synthesis of pyrido[4,3-d]pyrimidin-2-ones

  2013cites this paper
• Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents.

  2010cites this paper
• Novel 8-deaza-5,6,7,8-tetrahydroaminopterin derivatives as dihydrofolate inhibitor: design, synthesis and antifolate activity.

  2009cites this paper
• Bicyclic 6-6 Systems: Three Heteroatoms 1:2

  2008cites this paper
• Novel probes showing specific fluorescence enhancement on binding to a hexahistidine tag.

  2008cites this paper
• 2,4-Diaminopteridine-Based Compounds as Precursors for De Novo Synthesis of Antifolates: a Novel Class of Antimalarials

  2005cites this paper
• Zipper-featured delta-peptide foldamers driven by donor--acceptor interaction. Design, synthesis, and characterization.

  2004cites this paper
• Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

  2004cites this paper
• SCALABLE SYNTHESES OF N α-BENZYLOXYCARBONYL-l-ORNITHINE AND OF N α-(9-FLUORENYLMETHOXY)CARBONYL-l-ORNITHINEE

  2002cites this paper
• Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues.

  2001cites this paper
• Parallel synthesis of a small library of novel aminoglycoside analogs based on 2-amino-2-deoxy-d-glucose and d-ribose scaffolds

  2001cites this paper
• Chemically induced dimerization of dihydrofolate reductase by a homobifunctional dimer of methotrexate.

  2000cites this paper
• Development of Nonpolyglutamatable DHFR Inhibitors

  1999cites this paper
• 5-deazafolate analogues with a rotationally restricted glutamate or ornithine side chain: synthesis and binding interaction with folylpolyglutamate synthetase.

  1999cites this paper
• Synthesis and Potent Antifolate Activity and Cytotoxicity of B-Ring Deaza Analogues of the Nonpolyglutamatable Dihydrofolate Reductase Inhibitor Nα-(4-Amino-4-deoxypteroyl)-Nδ-hemiphthaloyl-l-ornithine (PT523)

  1998cites this paper
• ELECT++: Faster conformational search method for docking flexible molecules using molecular similarity

  1998cites this paper
• Synthesis and potent antifolate activity and cytotoxicity of B-ring deaza analogues of the nonpolyglutamatable dihydrofolate reductase inhibitor Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl- L-ornithine (PT523).

  1998cites this paper
• Inhibition of folylpolyglutamate synthetase by substrate analogues with an ornithine side chain

  1996cites this paper
• Design and synthesis of histidine analogues of folic acid and methotrexate as potential folylpolyglutamate synthetase inhibitors.

  1996cites this paper
• 7.16 – Bicyclic 6-6 Systems: Three Heteroatoms 1:2

  1996cites this paper
• Phase-selective AC adsorptive stripping voltammetric assay for aminopterin and 10-Edam in human serum.

  1993cites this paper
• Phase-selective alternating current adsorptive stripping voltammetry of aminopterin on a mercury thin film carbon fibre ultramicroelectrode

  1993cites this paper
• Synthesis of methotrexate-dimyristoylphosphatidylethanolamine analogs and characterization of methotrexate release in vitro

  1992cites this paper
• Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation.

  1992cites this paper
• Overview: Recent Developments in Anticancer Agents

  1991cites this paper