79640-68-9

Upstream product

• 6234-01-1 L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 50734-07-1 4-[N-methyl-N-(trifluoroacetyl)amino]benzoic acid 
• 95063-86-8 p-[N-methyl-N-(trifluoroacetyl)amino]benzoyl chloride 
• 945-24-4 2,4-diamino-6-(hydroxymethyl)pteridine 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 95485-08-8 α-methyl γ-tert-butyl N--L-glutamate 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 53838-27-0 H-Glu(tBu)-OMe 
• 2942-58-7 diethyl cyanophosphonate 
• 95485-07-7 α-methyl γ-tert-butyl N-benzoyl>-L-glutamate 

Downstream Products

• 79640-76-9 γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-glutamate 
• 66147-29-3 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid 1-methyl ester 
• 913625-16-8 6-((S)-4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-hexanoic acid 
• 913625-15-7 6-(4-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-hexanoic acid tert-butyl ester 
• 913625-20-4 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5-diacetoxy-2-acetoxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester 
• 913625-19-1 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester 
• 913625-18-0 C₅₃H₇₁FN₁₀O₂₀S 
• 913625-17-9 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-(5-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-pentylcarbamoyl)-butyric acid methyl ester 

Relevant academic research and scientific papers

Optimized design and synthesis of chemical dimerizer substrates for detection of glycosynthase activity via chemical complementation

Glycosynthases catalyze the formation of a glycosidic bond between a glycosyl fluoride donor substrate and a glycosyl acceptor substrate with high yield, thus providing a valuable approach for the synthesis of carbohydrates and glycoconjugates. Chemical c

Methotrexate analogues. 25. Chemical and biological studies on the γ-tert-Butyl esters of methotrexate and aminopterin

γ-tert-Butylaminopterin (γ-tBAMT), the first example of an aminopterin (AMT) γ-monoester, was synthesized, and new routes to the known N10-methyl analogue γ-tert-butyl methotrexate (γ-tBMTX were developed. The inhibitory effects of γ-tBAMT on the activity of purified dihydrofolate reductase (DHFR) from L1210 murine leukemia cells, the growth of L1210 cells and CEM human leukemic lymphoblasts in suspension culture, and the growth of several lines of human squamous cell carcinoma of the head and neck in monolayer culture were compared with the effects of γ-tBMTX and the parent acids AMT and methotrexate (MTX). Patterns of cross-resistance to γ-tBAMT, γ-tBMTX, and AMT among several MTX-resistant cell lines were examined. In vivo antitumor activities of γ-tBAMT and γ-tBMTX were compared in mice with L1210 leukemia. While the activity of γ-tBAMT was very close to that of γ-tBMTX in the DHFR inhibition assay, the AMT ester was more potent than the MTX ester against cells in culture and against L1210 leukemia in vivo. Only partial cross-resistance was shown against γ-tBMTX and γ-tBAMT in cultured cells that were resistant to MTX by virtue of a transport defect or a combination of defective transport and elevated DHFR activity.

Methotrexate Analogues. 14. Synthesis of New γ-Substituted Derivatives as Dihydrofolate Reductase Inhibitors and Potential Anticancer Agents

The γ-tert-butyl ester (1), γ-hydrazide (2), γ-n-butylamide (3), and γ-benzylamide (4) derivatives of methotrexate (MTX) were synthesized from 4-amino-4-deoxy-N10-methylpteroic acid (APA) and the appropriate blocked L-glutamic acid precursors with the aid of the peptide bond forming reagent diethyl phosphorocyanidate.The affinity of these side chain modified products for dihydrofolate reductase (DHFR) from Lactobacillus casei and L1210 mouse leukemic cells was determined spectrophotometrically or by competitive radioligand binding assay, and their cytotoxicity was evaluated against L1210 leukemic cells in culture.The results provide continuing support for the view that the "γ-terminal region" of the MTX side chain is an attractive site for molecular modification of this anticancer agent.