5-deazafolic acid

Base Information

• Chemical Name: 5-deazafolic acid
• CAS No.: 85597-17-7
• Molecular Formula: C20H20 N6 O6
• Molecular Weight: 440.4094
• Mol file: 85597-17-7.mol

Synonyms:L-Glutamicacid, N-[4-[[(2-amino-1,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-6-yl)methyl]amino]benzoyl]-(9CI); Pyrido[2,3-d]pyrimidine, L-glutamic acid deriv.; 5-Deazafolic acid; NSC344279

Chemical Property of 5-deazafolic acid

Chemical Property:

• PSA: 200.39000
• Density: 1.61g/cm³
• LogP: 1.60530

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-deazafolic acid

There total 7 articles about 5-deazafolic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diethyl N-(p-aminobenzoyl)-L-glutamate (13726-52-8) → 5-deazafolic acid (85597-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / 70percent CH₃COOH, H₂ / Raney Ni / 17 h / 25 °C

2: 1.) O₂-free 1 N NaOH, 2.) 6 N HCl / 1.) reflux, 4.25 h, 2.) pH 3.1

With hydrogenchloride; sodium hydroxide; hydrogen; acetic acid; nickel;

DOI:10.1021/jo00344a002

Reference yield:

2,4-diamino-6-(dimethoxymethyl)-5-deazapteridine (87373-66-8) → L-5-deazafolic acid (85597-17-7)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOH / H₂O / 2.5 h / Heating

2: 97 percent / 88 percent formic acid / 1 h / Ambient temperature

3: 12 h / Heating

4: acetic acid / 6 h

5: borane-triethylamine / acetic acid / 0.67 h / Ambient temperature

6: 80 percent / 0.1 N NaOH / 80 °C

With sodium hydroxide; formic acid; triethylamine-borane; In water; acetic acid;

DOI:10.1021/jo00173a014

Reference yield:

2-acetamido-6-formyl-4(3H)-oxopyrido<2,3-d>pyrimidine (87373-56-6) → L-5-deazafolic acid (85597-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / 6 h

2: borane-triethylamine / acetic acid / 0.67 h / Ambient temperature

3: 80 percent / 0.1 N NaOH / 80 °C

With sodium hydroxide; triethylamine-borane; In acetic acid;

DOI:10.1021/jo00173a014

upstream raw materials:

diethyl N-(p-aminobenzoyl)-L-glutamate

2,4-Diamino-6-(carboxaldehyde)pyrido[2,3-d]pyrimidine

2-amino-4(3H)-oxopyrido<2,3-d>pyrimidine-6-carboxaldehyde

2,4-diamino-6-(dimethoxymethyl)-5-deazapteridine

Downstream raw materials:

5-deaza-10-methylfolic acid

Refernces

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

10.1021/jm00087a012

This research aimed to synthesize and evaluate a series of 5-deazafolate and 5-deazatetrahydrofolate analogues as potential inhibitors of folylpolyglutamate synthetase (FPGS) and glycinamide ribonucleotide formyltransferase (GARFT), enzymes involved in folate metabolism and purine biosynthesis, respectively. The researchers synthesized analogues by replacing the glutamic acid side chain with homocysteic acid (HCysA), 2-amino-4-phosphonobutanoic acid (APBA), and ornithine (Om). The compounds were tested for their inhibitory effects on mouse liver FPGS and GARFT. The results showed that the analogues with HCysA and monoethyl APBA side chains were less active as FPGS inhibitors, while Orn and APBA analogues exhibited competitive inhibition kinetics and were more potent, with Ki values as low as 30 nM.

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