13161-88-1

Upstream product

• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 95-51-2 o-chloroaniline 
• 116374-65-3 4-chloro-9-<<3-(dimethylamino)propyl>amino>-1-nitroacridine 
• 107210-27-5 5'-nitro-2'-chloro-2-carboxy-diphenylamine 

Downstream Products

• 128071-39-6 1-nitro-4-(2'-amino-ethylamino)-9-acridinone 
• 121083-75-8 1-nitro-4-chloro-10-methyl-9-acridinone 
• 75586-66-2 1-nitro-4,9-dichloro-acridine 
• 128093-92-5 1-nitro-4,9-diethylthio-acridine 
• 148902-86-7 1-nitro-4-(2'-amino-ethylamino)-10-methyl-9-acridinone 

Relevant academic research and scientific papers

Synthesis and antiparasitic activity of new 1-nitro, 1-amino and 1-acetamido 9-acridinones

The synthesis of 1-amino-10-alkyl-9-acridinones 4 and 5 and of homologous 9-thio-acridinones 7 and 8 are described. Similarly, the synthesis of 1-nitro-4-(2'-aminoethylamino)-9-acridinones 13 and 15, is described. Compound 4 was used as starting material for the preparation of 10-alkyl-9-acridinone dimers 6, bridged with an α,ω-diamido chain. Compound 15 was selected for biological investigations on pathogenic parasite strains, and a promising antiamoebic activity could be shown.

Substituent Effects on the Hydrolysis of Analogues of Nitracrine -1-nitroacridine>

Studies of the hydrolysis of the hypoxia-selective cytotoxic agent 9--1-nitroacridine (nitracrine) and several of its 4-substituted analogues and nitro-positional isomers have been carried out.Examination of the effects of pH and temperature on the hydrolysis of nitracrine itself shows that the reaction is subject to acid catalysis.The value of ΔH(excit.) increases from 46 to 63 kJ mol-1 as the pH falls from 6 to 3, while the value of ΔS(excit.) increases from -195 to -138 J k-1 mol-1.The rate constants for hydrolysis and the acid dissociation constants have been measured at pH 5 and 60 deg C.Both the rate constants of hydrolysis, corrected for the substrate-protonation equilibrium, and the substrate-acid association constants are well fitted by the Ehrenson-Brownlee-Taft dual-substituent-parameter ?R- relationship.The Swain-Unger-Rosenquist-Swain relationship shows weak correlation but the linear free-energy relationships of Hammett and Yukawa-Tsuno are not fitted.The results are discussed in terms of the resonance interactions of the possible intermediates in the hydrolysis pathways.

Synthesis and Cyclization Reactions of 4--9-(3-Dimethylaminopropylamino)-1-Nitroacridines: Approaches to the Synthesis of 'Nitracrine Mustard'

Compounds which can be selectively activated to cytotoxic species in hypoxic mammalian cells have potential for the treatment of solid tumours, which uniquely contain cells in such an environment.One approach to such drugs is exemplified by the title comp