106585-56-2

Basic information

• Product Name: diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate
• Synonyms: diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate
• CAS NO: 106585-56-2
• Molecular Weight: 340.352
• Mol File: 106585-56-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate(106585-56-2)
• EPA Substance Registry System: diethyl N-(4-amino-2-fluorobenzoyl)-L-glutamate(106585-56-2)

Safety Data

• Hazardous Substances Data: 106585-56-2(Hazardous Substances Data)

Upstream product

• 1427-07-2 2-fluoro-4-nitrotoluene 
• 75-09-2 dichloromethane 
• 7439-89-6 iron 
• 106585-55-1 diethyl N-(2-fluoro-4-nitrobenzoyl)-L-glutamate 
• 403-23-6 2-fluoro-4-nitrobenzoyl chloride 
• 403-24-7 2-fluoro-4-nitrobenzoic acid 

Downstream Products

• 106585-57-3 diethyl N-(2-fluoro-4-(N-prop-2-ynylamino)benzoyl)-L-glutamate 
• 153505-91-0 diethyl N-(4-(((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methyl)-amino)-2-fluorobenzoyl)-L-glutamate 
• 112887-67-9 N-<4--N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamic acid 
• 129175-42-4 (S)-2-{4-[(3-Acetoxy-propyl)-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid diethyl ester 
• 129193-66-4 (S)-2-{4-[Cyanomethyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid diethyl ester 
• 129175-36-6 diethyl N-<4--N-prop-2-ynylamino>-2-fluorobenzoyl>-L-glutamate 
• 129175-39-9 (S)-2-{4-[Ethyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid diethyl ester 
• 112887-98-6 (S)-2-{4-[Carbamoylmethyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid 
• 129175-40-2 (S)-2-{4-[Allyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid diethyl ester 
• 129175-20-8 (S)-2-{2-Fluoro-4-[(3-hydroxy-propyl)-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid 
• 129175-38-8 (S)-2-{2-Fluoro-4-[methyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid diethyl ester 
• 112887-66-8 N-p-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-ethylamino]-o-fluorobenzoyl-L-glutamic acid 
• 129175-19-5 (S)-2-{4-[Allyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-2-fluoro-benzoylamino}-pentanedioic acid 
• 112887-65-7 N-p-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino]-o-fluorobenzoyl-L-glutamic acid 

Relevant articles and documents

Anti-cancer quinazoline derivatives

A compound of formula I: STR1 wherein R is hydrogen; oran alkyl, alkenyl or alkynyl group of up to 6 carbon atoms; nis O; 1 or 2; Z represents --CH=CH-- or --S--; each X independently represents halogeno, C1 -C4 alkyl, C1 -C4 alkoxy, nitro or trifluoromethyl; and Y represents a group of formula: STR2 or a pharmaceutically acceptable salt or ester thereof.

Quinazoline antifolate thymidylate synthase inhibitors: Benzoyl ring modifications in the C2-methyl series

The synthesis of nine new 2-methyl-10-propargylquinazoline antifolates with substituents in the p-aminobenzoyl ring is described. In general the synthetic route involved the coupling of the appropriate ring-substituted diethyl N-[4-(prop-2-ynylamino)benzoyl]-L-glutamate with 6-(bromomethyl)-3,4-dihydro-2-methyl-4-oxoquinazoline (11) followed by deprotection using mild alkali. The compounds were tested as inhibitors of partially purified L1210 thymidylate synthase (TS). They were also examined for their inhibition of the growth L1210 cells in culture. Compared to the parent compound 1a the 2'-fluoro analogue 2a exhibited enhanced potency in both systems whereas the 3'-fluoro analogue 3a showed enhanced growth inhibitory properties against L1210 cells despite being a poorer inhibitor of the isolated enzyme. Chloro, hydroxy, methoxy, and nitro substituents in the 2'-position were also well tolerated by the enzyme but failed to give enhanced growth inhibition. The series was extended to cover analogues of the 2'-fluoro, 3'-fluoro, 2'-chloro, 2'-methyl, 2'-amino, 2'-methoxy, and 2'-nitro derivatives with modified alkyl substituents at N10.