95693-76-8

Usage

Uses

Used in Biochemical Research:
5,10-Dideazatetrahydrofolic acid is used as a research tool for studying the metabolism of folate and the activity of dihydrofolate reductase, an enzyme pivotal in nucleotide biosynthesis.
Used in Antimicrobial Applications:
5,10-Dideazatetrahydrofolic acid is used as an antimicrobial agent for inhibiting the growth of certain microorganisms by interfering with their folic acid metabolism.
Used in Cancer Treatment:
5,10-Dideazatetrahydrofolic acid is used as a potential chemotherapeutic agent for the treatment of various types of cancer, especially those that depend on folate for growth and proliferation.
Used in Pharmaceutical Development:
5,10-Dideazatetrahydrofolic acid is utilized in the development of pharmaceuticals to explore its therapeutic applications and understand its pharmacological properties and potential side effects, with the aim of advancing its use in clinical settings.

InChI:InChI=1/C21H25N5O6/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28/h3-6,12,15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30)/t12?,15-/m0/s1

Upstream product

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• 111291-97-5 4-ethynylbenzoic acid tert-butyl ester 
• 116387-40-7 methyl 5-iodo-2-oxo-1,2-dihydro-3-pyridinecarboxylate 
• 609-71-2 1,2-dihydro-2-oxonicotinic acid 
• 110672-49-6 (S)-2-{4-[2-((R)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 136210-14-5 (R)-(-)-4-<2-(2-Amino-1,4,5,6,7,8-hexahydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethyl>benzonic acid 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 4654-39-1 4-bromophenethanol 
• 84913-19-9 4-methylbenzene sulfonic acid 2-(4-bromophenyl)ethyl ester 
• 127633-49-2 (3RS,5S)-5-<2-(4-Bromophenyl)ethyl>-2-oxo-3-piperidinecarboxylic acid ethyl ester 
• 246043-59-4 (3RS,5R)-5-<2-(4-Bromophenyl)ethyl>-2-oxo-3-piperidinecarboxylic acid ethyl ester 
• 127633-50-5 (S)-2-Amino-6-<2-(4-bromophenyl)ethyl>-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-4(3H)-one 
• 127633-51-6 (R)-(-)-2-Amino-6-<2-(4-bromophenyl)ethyl>-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-4(3H)-one 

Relevant academic research and scientific papers

Synthesis of (6R)- And (6S)-5,10-dideazatetrahydrofolate oligo-γ-glutamates: Kinetics of multiple glutamate ligations catalyzed by folylpoly-γ-glutamate synthetase

Folylpoly-γ-glutamate synthetase (FPGS, EC 6.3.2.17) catalyzes the ATP-dependent ligation of glutamic acid to reduced folates including (6S)-5,6,7,8-tetrahydrofolate (H4PteGlu), as well as to anticancer drugs such as 5,10-dideaza-5,6,7,8-tetrahydrofolate ((6R)-DDAH 4PteGlu1, (6R)-DDATHF, Lometrexol(tm)). Synthesis of unlabeled mono- and polyglutamates, DDAH4PteGlu n (6R, n = 1-6; 6S, n = 1-2), as well as (6R)-DDAH 4Pte[14C]Glu1, was effected from (6R)- or (6S)-5,10-dideazatetrahydropteroyl azide and glutamic acid, H-Glu-γ- Glun-y-Glu-OH (n = 0-4), or [14C]glutamic acid, respectively. These compounds were evaluated as FPGS substrates to determine steady-state kinetic constants. Michaelis-Menten kinetics were observed for (6-R)-DDAH4PteGlu1, the isomer corresponding to H 4PteGlu, whereas marked substrate inhibition was observed for (6S)-DDAH4PteGlun (n = 1-2) and (6R)-DDAH 4PteGlun (n = 2-5), but not (6.R)-DDAH 4PteGlu6. Multiple ligation of glutamate renders a quantitative analysis of these data difficult. However, approximate values of KM = 0.65-1.6 μM and K1, = 144-417 μM for DDAH 4PteGln were obtained using a simple kinetic model. The Royal Society of Chemistry 2005.

Asymmetric synthesis of lometrexol ((6R)-5,10-dideaza-5,6,7,8-tetrahydrofolic acid)

An enantioselective synthesis of lometrexol (1) which utilizes (5R)-2-piperidone 18 as a key intermediate is described. Lipase-catalyzed enantioselective esterification of 1,3-propanediol derivative 5 provided (R)-(+)-6, the absolute configuration of whic

Enantioselective synthesis of antifolates

A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.

Process for the preparation of fused pyridine compounds

Pyrido[2,3-d]pyrimidine compounds are prepared through the reaction of 2,4-diamino-6(1H)-pyrimidone and an activated derivative of a dialdehyde. A typical embodiment utilizes the dinitrile.

Diastereoisomeric tetrahydropyrido-(2,3,d) pyrimidine derivatives

The diastereoisomeric forms of N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid are antineoplastic agents. The compounds are prepared by separation of the diastereoisomeric form of the correspondingl

Asymmetric synthesis and absolute configuration of 5,10-dideaza-5,6,7,8-tetrahydropteroic acid and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

Lipase-catalyzed enantioselective esterification of 2-substituted 1,3-diols has been utilized in the asymmetry synthesis and consequent configurational assignments of the title compounds.

Synthesis and Antifolate Activity of 5-Methyl-5,10-dideaza Analogues of Aminopterin and Folic Acid and an Alternative Synthesis of 5,10-Dideazatetrahydrofolic Acid, a Potent Inhibitor of Glycinamide Ribonucleotide Formyltransferase

The title compounds were prepared in extensions of a general synthetic approach used earlier to prepare 5-alkyl-5-deaza analogues of classical antifolates.Wittig condensation of 2,4-diaminopyridopyrimidine-6-carboxaldehyde (2a) and its 5-methyl ana

Synthesis of the Antileucemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin

Total syntheses from pyridine precursors of 5,10-dideazaaminopterin (1) and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin (2) are described.These compounds exhibit significant in vivo activity against L1210 leukemia that comparable to that observed with meth