114304-24-4

Upstream product

• 645-59-0 dihydrocinnamonitrile 
• 15121-84-3 2-nitro-benzeneethanol 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 69628-96-2 p-toluenesulfonic acid o-nitrophenethyl ester 
• 151-50-8 potassium cyanide 

Downstream Products

• 2001-32-3 3-(2-nitrophenyl)propionic acid 
• 650629-19-9 5'-(3-(2-nitrophenyl)propionyl)-2'-deoxy-5-fluorouridine 
• 650629-24-6 5'-(3-(2-aminophenyl)propionyl)-2'-deoxy-5-fluorouridine 
• 1664-65-9 3-(2-nitrophenyl)propionic acid methyl ester 
• 580-22-3 2-aminoquinoline 

Relevant academic research and scientific papers

5′-(2-Nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation

Four 5′-(2-nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two methyl groups were introduced α to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chemical reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic analysis of the cyclization activation process indicates that the two methyl groups α to the ester carbonyl restrict the rotational freedom of ground state molecule and promote the cyclization reaction. However, the two methyl groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two methyl groups, was reduced by E. coli B nitroreductase (t1/2=8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymatic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation.

Experiments on the Chaperon effect in the nitration of aromatics

A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.