130296-53-6

Basic information

• Product Name: N-<4-methyl>-N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamic acid
• CAS NO: 130296-53-6
• Molecular Weight: 510.479
• Mol File: 130296-53-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-<4-methyl>-N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-<4-methyl>-N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamic acid(130296-53-6)
• EPA Substance Registry System: N-<4-methyl>-N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamic acid(130296-53-6)

Safety Data

• Hazardous Substances Data: 130296-53-6(Hazardous Substances Data)

Upstream product

• 106585-55-1 diethyl N-(2-fluoro-4-nitrobenzoyl)-L-glutamate 
• 106585-57-3 diethyl N-(2-fluoro-4-(N-prop-2-ynylamino)benzoyl)-L-glutamate 
• 106585-56-2 diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate 
• 403-23-6 2-fluoro-4-nitrobenzoyl chloride 
• 403-24-7 2-fluoro-4-nitrobenzoic acid 
• 1427-07-2 2-fluoro-4-nitrotoluene 
• 130296-58-1 diethyl N-<4-methyl>-N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamate 

Relevant articles and documents

Quinazoline Antifolate Thymidylate Synthase Inhibitors: 2'-Fluoro-N10-propargyl-5,8-dideazafolic Acid and Derivatives with Modifications in the C2 Position

The synthesis of 2'-fluoro-10-propargyl-5,8-dideazafolic acid and its 2-desamino, 2-desamino-2-hydroxymethyl, and 2-desamino-2-methoxy analogues is described.In general the synthetic route involved the coupling of diethyl N--L-glutamate (15) with the appropriate 6-(bromomethyl)quinazoline followed by deprotection with mild alkali.These four compounds together with the 2-desamino-2-methyl analogue were tested for their activity against L1210 thymidylate synthase (TS).They were also examined for their inhibition of the growth of the L1210 cell line and of two mutant L1210 cell lines, the L1210:R7A that overproduces dihydrofolate reductase (DHFR) and the L1210:1565 that has impaired uptake of reduced folates.Compared with their nonfluorinated parent compounds, the 2'-fluoro analogues were all ca. 2-fold more potent as TS inhibitors.Similarly, they also showed improved inhibition of L1210 cell growth (1.5-5-fold), and this activity was prevented by co-incubation with thymidine.All had retained or improved activity against both the L1210:R7A and L1210:1565 cell lines.