52454-37-2

Basic information

• Product Name: 10-deazaaminopterin
• Synonyms: 10-deazaaminopterin;(2S)-2-[4-[2-(2,4-Diamino-6-pteridinyl)ethyl]benzoylamino]glutaric acid;N-[4-[2-(2,4-Diaminopteridin-6-yl)ethyl]benzoyl]-L-glutamic acid;N-[4-[2-(2,4-Diaminopteridine-6-yl)ethyl]benzoyl]-L-glutamic acid
• CAS NO: 52454-37-2
• Molecular Formula: C₂₀H₂₁N₇O₅
• Molecular Weight: 439.42
• Mol File: 52454-37-2.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.512g/cm³
• Refractive Index: 1.715
• CAS DataBase Reference: 10-deazaaminopterin(CAS DataBase Reference)
• NIST Chemistry Reference: 10-deazaaminopterin(52454-37-2)
• EPA Substance Registry System: 10-deazaaminopterin(52454-37-2)

Safety Data

• Hazardous Substances Data: 52454-37-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
10-Deazaaminopterin is used as a therapeutic agent for the treatment of certain diseases, particularly those involving the immune system. Its ability to inhibit neutrophil chemotaxis and superoxide generation makes it a promising candidate for conditions characterized by excessive inflammation or immune response.
Additionally, 10-Deazaaminopterin is used as a Pralatrexate impurity. Pralatrexate is an antifolate chemotherapy drug used to treat certain types of cancer, and 10-Deazaaminopterin is one of the impurities that may be present in the synthesis or formulation process of Pralatrexate. Monitoring and controlling the levels of this impurity is essential to ensure the safety and efficacy of the final drug product.

InChI:InChI=1/C20H21N7O5/c21-16-15-17(27-20(22)26-16)23-9-12(24-15)6-3-10-1-4-11(5-2-10)18(30)25-13(19(31)32)7-8-14(28)29/h1-2,4-5,9,13H,3,6-8H2,(H,25,30)(H,28,29)(H,31,32)(H4,21,22,23,26,27)

Upstream product

• 80577-71-5 (S)-2-{4-[2-(2,4-Diamino-pteridin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 96056-44-9 4-[2-(2,4-Diamino-7,8-dihydro-pteridin-6-yl)-ethyl]-benzoic acid 
• 96056-27-8 4-(p-carbomethoxyphenyl)-1-phthalimido-3-buten-2-one 
• 96056-32-5 1-phthalimido-4-(p-carbomethoxyphenyl)-2-butanone 
• 96056-35-8 1-phthalimido-4-(p-carbomethoxyphenyl)-2-butanone oxime 
• 96056-41-6 4-[4-(2,6-Diamino-5-nitro-pyrimidin-4-ylamino)-3-oxo-butyl]-benzoic acid methyl ester 
• 96095-24-8 (2-oxo-3-phthalimidopropyl)(triphenyl)phosphonium bromide 
• 603-35-0 triphenylphosphine 
• 33047-42-6 4-<(2,4-diaminopteridin-6-yl)ethyl>benzoic acid 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 99-94-5 p-Toluic acid 
• 80577-69-1 2-bromo-4-(4-carboxyphenyl)butanal 
• 56277-36-2 diethyl 4-formylbenzoyl-L-glutamate 
• 72716-32-6 6-[(Triphenyl-λ⁵-phosphanylidene)-methyl]-pteridine-2,4-diamine 

Relevant articles and documents

Folate Analogues. 24. Syntheses of the Antitumor Agents 10-Deazaaminopterin (10-DAAM) and 10-Ethyl-10-deazaaminopterin (10-EDAAM)

Methods have been developed for the chemical synthesis of two recently described potent antitumor agents.They are 10-deazaaminopterin (10-DAAM) (2) and 10-ethyl-10-deazaaminopterin (10-EDAAM) (3).The methods described in this paper have general applicability for the synthesis of a variety of hitherto difficulty accessible 10-substituted-10-deazafolic acids and analogues.Reaction of methyl p-formylbenzoate (7) with the Wittig reagent 6 derived from N-(3-bromo-2-oxopropyl)phtalimide (5) and triphenylphosphine gave the common intermediate 8, which was used for the synthesis of both 2 and 3.This enone was reduced with Zn/HOAc to 15 and was used for the synthesis of 2.Alternately 8 was reacted with ethylmagnesium bromide in the presence of cuprous bromide to obtain the conjugate addition product 16.Both 15 and 16 were converted to the masked α-amino ketones 20 and 21 reacted with 6-chloro-2,4-diamino-5-nitropyrimidine to obtain 22 and 23.These pyrimidine intermediates were subsequently elaborated to the pteroic acid analogues 26 and 27 by multistep procedures previously described from this laboratory.The target compounds 2 and 3 were prepared from 26 and 27 by standard coupling procedures involving isobutyl chloroformate and diethyl L-glutamate.

Convenient Synthesis of 10-Deazaaminopterin via a Pteridine Ylide

10-Deazaaminopterin, a potential antitumor agent now undergoing clinical trials, has been synthesized by a new approach involving the Wittig reaction.The ylide obtained by reaction of 6-(bromomethyl)-2,4-pteridinediamine with triphenylphosphine in Me2NAc,

Process for the preparation of 10-deazaaminopterin and related compounds

There is disclosed an improved process for the preparation of 10-deazaaminopterin and related compounds. In accordance with this process, 6-(bromomethyl)-2,4-pteridinediamine hydrobromide is reacted with triphenylphosphine to form a phosphonium salt which