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Analogues of the potent nonpolyglutamatable antifolate N(alpha)-(4-amino-4-deoxypteroyl)-N(delta)-hemiphthaloyl-L-ornithine (PT523) with modifications in the side chain, p-aminobenzoyl moiety, or 9,10-bridge: synthesis and in vitro antitumor activity

Autor: A, Rosowsky, J E, Wright, C M, Vaidya, R A, Forsch, H, Bader

Publikováno v: Journal of medicinal chemistry. 43(8)

Seven N(alpha)-(4-amino-4-deoxypteroyl)-N(delta)-hemiphthaloyl-L-o rnithine (2, PT523) analogues were synthesized by modifications of the literature synthesis of the corresponding AMT (1) analogues and were tested as inhibitors of tumor cell growth.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::861efbe706d63966c13c5c21b56ed18c
https://pubmed.ncbi.nlm.nih.gov/10780919

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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)

Autor: A, Rosowsky, J E, Wright, C M, Vaidya, H, Bader, R A, Forsch, C E, Mota, J, Pardo, C S, Chen, Y N, Chen

Publikováno v: Journal of medicinal chemistry. 41(26)

Six new B-ring analogues of the nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloy l-L-ornithine (PT523, 3) were synthesized with a view to determining the effect of modifications at the 5- and/or 8-position on dihydro

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::61aa37fa339c6e34d00699c16b230bad
https://pubmed.ncbi.nlm.nih.gov/9857098

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Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation

Autor: A, Rosowsky, R A, Forsch, V E, Reich, J H, Freisheim, R G, Moran

Publikováno v: Journal of medicinal chemistry. 35(9)

5-Deazafolate and 5-deazatetrahydrofolate (DATHF) analogues with the glutamic acid side chain replaced by homocysteic acid (HCysA), 2-amino-4-phosphonobutanoic acid (APBA), and ornithine (Orn) were synthesized as part of a larger program directed tow

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::ccb6bb69f053df9dd28148bf35cd256f
https://pubmed.ncbi.nlm.nih.gov/1578484

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Tetramethylmesoxalamide and Tetramethyl-1,3-Dithiomesoxalamide

Autor: J. C. Beckman, G. Skowronski, R. A. Forsch, E. Campaigne

Publikováno v: Synthetic Communications. 6:387-397

The chemistry of mesoxalic acid derivatives was investigated many years ago.2 For example, Curtiss demonstrated that dimethyl mesoxalate added ethanol to produce a stable isolatable hemiketal,3 whereas the corresponding diethyl ester presumably gave

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::343988f92d800d2f3a8cb5938462da69
https://doi.org/10.1080/00397917608063541

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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

Autor: A, Rosowsky, R C, Moran, R A, Forsch, M, Radike-Smith, P D, Colman, M M, Wick, J H, Freisheim

Publikováno v: Biochemical pharmacology. 35(19)

gamma-Phosphonate analogues of methotrexate (MTX) and aminopterin (AMT) were synthesized from 4-amino-4-deoxy-N10-methylpteroic acid and 4-amino-4-deoxy-N10-formylpteroic acid, respectively, by reaction with methyl D,L-2-amino-4-phosphonobutyrate fol

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::ec0313b160c253b9b4f5616c13703d73
https://pubmed.ncbi.nlm.nih.gov/3768024

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Methotrexate analogues. 21. Divergent influence of alkyl chain length on the dihydrofolate reductase affinity and cytotoxicity of methotrexate monoesters

Autor: R. A. Forsch, G. P. Beardsley, C. S. Yu, Herbert Lazarus, Andre Rosowsky

Publikováno v: Journal of medicinal chemistry. 27(5)

n-Octyl, n-dodecyl, and n-hexadecyl alpha- and gamma-esters of methotrexate (MTX) were compared with the previously described alpha- and gamma-n-butyl esters and with MTX as inhibitors of dihydrofolate reductase (DHFR) and human leukemic lymphoblasts

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::73668b5639a36172bb8f670140984d79
https://pubmed.ncbi.nlm.nih.gov/6585550

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Regiospecific gamma-conjugation of methotrexate to poly(L-lysine). Chemical and biological studies

Autor: A, Rosowsky, R A, Forsch, J, Galivan, S S, Susten, J H, Freisheim

Publikováno v: Molecular pharmacology. 27(1)

Regiospecific syntheses of gamma- and alpha-conjugates of methotrexate and poly(L-lysine) are described. The alpha- and gamma-t-butyl esters, respectively, of methotrexate were coupled to poly(L-lysine) with diphenylphosphoryl azide in N,N-dimethylfo

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::820bd62fe796702a0dd7648a126a979c
https://pubmed.ncbi.nlm.nih.gov/3965926

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Synthesis and biologic activity of new side-chain-altered methotrexate and aminopterin analogs with dual inhibitory action against dihydrofolate reductase and folylpolyglutamate synthetase

Autor: A, Rosowsky, R G, Moran, J H, Freisheim, H, Bader, R A, Forsch, V C, Solan

Publikováno v: NCI monographs : a publication of the National Cancer Institute. (5)

Replacement of the glutamic acid (Glu) moiety in methotrexate (MTX) and aminopterin (AMT) by 2-amino-4-phosphonobutyric acid (APBA) and ornithine (Orn) has been found to give analogs that retain the ability to inhibit dihydrofolate reductase (DHFR) w

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=pmid________::1f7edf969d2c6e78d97bce8f70d222ec
https://pubmed.ncbi.nlm.nih.gov/3431589

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