52407-60-0

Basic information

• Product Name: N-(p-AMinobenzoyl)-L-glutaMic Acid DiMethyl Ester
• Synonyms: N-(p-AMinobenzoyl)-L-glutaMic Acid DiMethyl Ester
• CAS NO: 52407-60-0
• Molecular Formula: C₁₄H₁₈N₂O₅
• Molecular Weight: 294.30312
• Product Categories: Amino Acids & Derivatives, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 52407-60-0.mol

Chemical Properties

• Boiling Point: 505.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.234±0.06 g/cm3(Predicted)
• Solubility: DMSO. Methanol
• PKA: 13.66±0.46(Predicted)
• CAS DataBase Reference: N-(p-AMinobenzoyl)-L-glutaMic Acid DiMethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-AMinobenzoyl)-L-glutaMic Acid DiMethyl Ester(52407-60-0)
• EPA Substance Registry System: N-(p-AMinobenzoyl)-L-glutaMic Acid DiMethyl Ester(52407-60-0)

Safety Data

• Hazardous Substances Data: 52407-60-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(p-Aminobenzoyl)-L-glutamic Acid Dimethyl Ester is used as an intermediate in the synthesis of Folic Acid (F680300) for its role in DNA synthesis, DNA repair, and DNA methylation. Acting as a cofactor in biological reactions involving folate, it contributes to the production of new cells and the maintenance of overall cellular health.

Upstream product

• 67-56-1 methanol 
• 4271-30-1 N-(4-aminobenzoyl)-L-glutamic acid 
• 185116-43-2 4-(9H-fluoren-9-ylmethoxycarbonylamino)benzoic acid 
• 218603-08-8 dimethyl N-<4-benzoyl>-L-glutamate 
• 321527-88-2 tert-Butyl [4-(chlorocarbonyl)phenyl]carbamate 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 617-65-2 Glutamic acid 
• 150-13-0 4-amino-benzoic acid 
• 6525-53-7 glutamic acid dimethyl ether 

Downstream Products

• 67726-14-1 N-{4-[(2-oxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester 
• 67726-20-9 N-{4-[(2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester 
• 67726-26-5 N-{4-[(2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester 
• 72730-50-8 N-{4-[(5-methoxycarbonyl-2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester 
• 129082-61-7 dimethyl N<4-<2-(2,4-bis(acetylamino)-1,6-dihydro-6-oxo-5-pyrimidinyl)ethyl-N-methylamino>benzoyl>-L-glutamate 
• 87373-68-0 (S)-2-{4-[(2,4-Diamino-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid dimethyl ester 
• 129082-60-6 dimethyl N-<4-<2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino>benzoyl>-L-glutamate 
• 76282-79-6 N^2'-acetyl-5-deaza-7-L-<<<4-<<<1,3-bis(methoxycarbonyl)propyl>amino>carbonyl>phenyl>imino>methyl>pterin 
• 72244-64-5 dimethyl N-(3,5-dichloro-4-aminobenzoyl)-L-glutamate 
• 118869-56-0 dimethyl N-<4-<<(2-amino-3-cyanopyrazin-5-yl)methyl>amino>benzoyl>-L-glutamate 
• 161201-03-2 dimethyl N-<4-<<(2,4-diaminoquinazolin-5-yl)methyl>amino>benzoyl>-L-glutamate 
• 218603-30-6 N-<4-carbonyl>pyridin-2-ylmethyl)>aminobenzoyl>-L-glutamate 
• 118869-51-5 N-<4-<<(4-aminopteridin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 118252-47-4 N-<4-<2-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino>benzoyl>-L-glutamic acid 

Relevant articles and documents

Diastereoselective hydrogenation of folic acid esters with the Daniphos ligand

Folic acid dimethylester benzenesulfonate was hydrogenated homogeneously in a rhodium-catalyzed diastereoselective reaction employing a set of the previously published planar-chiral "Daniphos" ligands, which are based on an arene chromium tricarbonyl scaf

Exploring the ability of dihydropyrimidine-5-carboxamide and 5-benzyl-2,4-diaminopyrimidine-based analogues for the selective inhibition of L. major dihydrofolate reductase

To tackle leishmaniasis, search for efficient therapeutic drug targets should be pursued. Dihydrofolate reductase (DHFR) is considered as a key target for the treatment of leishmaniasis. In current study, we are interested in the design and synthesis of selective antifolates targeting DHFR from L. major. We focused on the development of new antifolates based on 3,4-dihydropyrimidine-2-one and 5-(3,5-dimethoxybenzyl)pyrimidine-2,4-diamine motif. Structure activity relationship (SAR) studies were performed on 4-phenyl ring of dihydropyrimidine (26–30) template. While for 5-(3,5-dimethoxybenzyl)pyrimidine-2,4-diamine, the impact of different amino acids (valine, tryptophan, phenylalanine, and glutamic acid) and two carbon linkers were explored (52–59). The synthesized compounds were assayed against LmDHFR. Compound 59 with the IC50 value of 0.10 μM appeared as potent inhibitors of L. major. Selectivity for parasite DHFR over human DHFR was also determined. Derivatives 55–59 demonstrated excellent selectivity for LmDHFR. Highest selectivity for LmDHFR was shown by compounds 56 (SI = 84.5) and 58 (SI = 87.5). Compounds Antileishmanial activity against L. major and L. donovani promastigotes was also performed. To explore the interaction pattern of the synthesized compounds with biological macromolecules, the docking studies were carried out against homology modelled LmDHFR and hDHFR targets.

The Synthesis and Preferred Conformation of Pyridoyl Urea and Analogous Derivatives. Preparation of a Folate Analogue

The synthesis of 2-pyridoyl urea and analogous derivatives is reported. Also the synthesis of a folate analogue, containing 2-pyridoyl urea instead of the pterine moiety, is described. NMR Spectra show that the acylureas adopt an intramolecular H-bonded c