14038-09-6Relevant articles and documents
Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer
Tokay, Esra,Güng?r, Tu?ba,Hac?o?lu, Nelin,?nder, Ferah C?mert,Gülhan, ünzile Güven,Tok, Tu?ba Ta?k?n,?elik, Ayhan,Ay, Mehmet,K??kar, Feray
, (2019/12/24)
Prodrugs for targeted tumor therapies have been extensively studied in recent years due to not only maximising therapeutic effects on tumor cells but also reducing or eliminating serious side effects on healthy cells. This strategy uses prodrugs which are safe for normal cells and form toxic metabolites (drugs) after selective reduction by enzymes in tumor tissues. In this study, prodrug candidates (1-36) containing nitro were designed, synthesized and characterized within the scope of chemical experiments. Drug-likeness properties of prodrug candidates were analyzed using DS 2018 to investigate undesired toxicity effects. In vitro cytotoxic effects of prodrug canditates were performed with MTT assay for human hepatoma cells (Hep3B) and prostate cancer cells (PC3) and human umbilical vein endothelial cells (HUVEC) as healthy control. Non-toxic compounds (3, 5, 7, 10, 12, 15, 17, 19 and 21–23), and also compounds (1, 2, 5, 6, 9, 11, 14, 16, 20 and 24) which had low toxic effects, were selected to examine their suitability as prodrug canditates. The reduction profiles and kinetic studies of prodrug/Ssap-NtrB combinations were performed with biochemical analyses. Then, selected prodrug/Ssap-NtrB combinations were applied to prostate cancer cells to determine toxicity. The results of theoretical, in vitro cytotoxic and biochemical studies suggest 14/Ssap-NtrB, 22/Ssap-NtrB and 24/Ssap-NtrB may be potential prodrug/enzyme combinations for nitroreductase (Ntr)-based prostate cancer therapy.
Deep Eutectic Solvent/Lipase: Two Environmentally Benign and Recyclable Media for Efficient Synthesis of N-Aryl Amines
Pant, Preeti Lalit,Shankarling, Ganapati Subray
, p. 1371 - 1378 (2017/08/29)
Abstract: Deep eutectic solvent (DES)/lipase catalyzed efficient synthesis of N-aryl amines from electron deficient aryl chlorides and amines at ambient temperature is reported. Its significant features include excellent yields of products, use of biodegradable, non-toxic and recyclable catalysts, thereby avoiding toxic metal catalyst/solvents making these protocols environmentally benign. Graphical Abstract: [Figure not available: see fulltext.].
KINETICS OF THE REACTION OF 2-(2,4-DINITROPHENOXY)-N-ETHYLPYRIDINIUM TETRAPHENYLBORATE WITH AROMATIC AMINES IN ACETONITRILE
Titskii, G. D.,Mitchenko, E. S.,Dubovaya, A. A.
, p. 1945 - 1949 (2007/10/02)
The reactions of 2-(2,4-dinitrophenoxy)-N-ethylpyridinium salts with arylamines take place by nucleophilic substitution at a carbon atom of the benzene ring with the formation of 2,4-dinitrodiphenylamine derivatives.The sensitivity coefficient (ρ0) to the induction effect of the substituents in the arylamine does not depend on the temperature in the range of 10-55 deg C and is equal to -6.89.The constant of the leaving group (τAr) for the 2-hydroxy-N-ethylpyridinium cation amounts to 1.66.
