95693-76-8

Basic information

• Product Name: 5,10-Dideazatetrahydrofolic
• Synonyms: 5,10-Dideazatetrahydrofolic;Dathf;L-Glutamic acid, N-(4-(2-(2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido(2,3-D)pyrimidin-6-yl)ethyl)benzoyl)-;L-GlutaMic acid, N-[4-[2-(2-aMino-3,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyriMidin-6-yl)ethyl]benzoyl]-;ZUQBAQVRAURMCL-CVRLYYSRSA-N
• CAS NO: 95693-76-8
• Molecular Formula: C₂₁H₂₅N₅O₆
• Molecular Weight: 443.4531
• Mol File: 95693-76-8.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.56 g/cm³
• Refractive Index: 1.709
• CAS DataBase Reference: 5,10-Dideazatetrahydrofolic(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-Dideazatetrahydrofolic(95693-76-8)
• EPA Substance Registry System: 5,10-Dideazatetrahydrofolic(95693-76-8)

Safety Data

• Hazardous Substances Data: 95693-76-8(Hazardous Substances Data)

Usage

General Description

5,10-Dideazatetrahydrofolic acid, also known as 5,10-DDATHF, is a synthetic compound that is structurally similar to the naturally occurring folate derivative, tetrahydrofolic acid. It has been widely used as a research tool in biochemistry for studying folate metabolism and the activity of dihydrofolate reductase, an enzyme involved in the biosynthesis of nucleotides. 5,10-DDATHF is also known to inhibit the growth of certain microorganisms by interfering with their folic acid metabolism. Additionally, this compound has shown potential as a chemotherapeutic agent for the treatment of various types of cancer, particularly those that are dependent on folate for their growth and proliferation. Despite its promising therapeutic applications, further research is needed to fully understand the pharmacological properties and potential side effects of 5,10-DDATHF.

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

• 116387-28-1 diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate 
• 10602-00-3 4-Ethynyl-benzoic 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 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 95674-71-8 4-<2-(2-amino-1,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethenyl>benzoic acid 
• 95674-66-1 2,4-diamino-6-(4-carboxystyryl)-5-deazapteridine 
• 95674-73-0 2-acetamide-6-(4-carboxystyryl)-5-deaza-4(3H)-pteridinone 
• 95674-65-0 2,4-diamino-6-<4-(tert-butoxycarbonyl)styryl>-5-deazapteridine 
• 95674-72-9 2-acetamido-6-<4-(acetoxycarbonyl)styryl>-5-deaza-4-(3H)-pteridinone 
• 95674-74-1 diethyl 2-acetyl-5,10-dideaza-9,10-didehydrofolate 
• 56-86-0 L-glutamic acid 
• 59247-47-1 tert-butyl-4-bromobenzoate 
• 155690-84-9 4-<2-(2-Amino-1,4,5,6,7,8-hexahydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethyl>benzonic acid 

Relevant articles and documents

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.

Enantioselective synthesis of antifolates

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

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