Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine
3-Nitropyridine reacted with nitrogen-centered carboxylic acid amide anions in anhydrous DMSO in the presence of K3Fe(CN)6 via oxidative nucleophilic substitution of hydrogen to give previously unknown N-(5-nitropyridin-2-yl) carboxa
Amangasieva,Borovlev,Demidov,Avakyan,Borovleva
p. 867 - 872
(2018/07/31)
Lowering the pKa of a bisimidazoline lead with halogen atoms results in improved activity and selectivity against Trypanosoma brucei in vitro
Diphenyl-based bis(2-iminoimidazolidines) are promising antiprotozoal agents that are curative in mouse models of stage 1 trypanosomiasis but devoid of activity in the late-stage disease, possibly due to poor brain penetration caused by their dicationic nature. We present here a strategy consisting in reducing the pKa of the basic 2-iminoimidazolidine groups though the introduction of chlorophenyl, fluorophenyl and pyridyl ring in the structure of the trypanocidal lead 4-(imidazolidin-2-ylideneamino)-N-(4-(imidazolidin-2-ylideneamino)phenyl)benzamide (1). The new compounds showed reduced pKa values (in the range 1-3 pKa units) for the imidazolidine group linked to the substituted phenyl ring. In vitro activities (EC50) against wild type and resistant strains of T. b. brucei (s427 and B48, respectively) were in the submicromolar range with four compounds being more active and selective than 1 (SI > 340). In particular, the two most potent compounds (3b and 5a) acted approximately 6-times faster than 1 to kill trypanosomes in vitro. No cross-resistance with the diamidine and melaminophenyl class of trypanocides was observed indicating that these compounds represent interesting leads for further in vivo studies.
Ríos Martínez, Carlos H.,Nué Martínez, J. Jonathan,Ebiloma, Godwin U.,De Koning, Harry P.,Alkorta, Ibon,Dardonville, Christophe
p. 806 - 817
(2015/08/06)
Synthesis and antibacterial activity of benzamides and sulfonamide derived from 2-amino-5-bromo/nitropyridine against bacterial strains isolated from clinical patients
A series of 5-(bromo/nitropyridin-2-yl)benzamide derivatives, viz. N-(5-bromopyridin-2-yl)benzamide 4a, 4-methyl-N-(5-bromopyridin-2-yl)benzamide 4b, 4-chloro-N-(5-bromopyridin-2-yl)benzamide 4c, 4-nitro-N-(5-bromopyridin-2- yl)benzamide 4d, N-(5-nitropyr
Rai, Diwakar,Singh, Ramendra K.
experimental part
p. 931 - 936
(2011/09/19)
Synthesis and characterization of N-(2-pyridyl)benzamide-based nickel complexes and their activity for ethylene oligomerization
A series of N-(2-pyridyl)benzamides (1)-(11) and their nickel complexes, [N-(2-pyridyl)benzamide]dinickel(II) di-μ-bromide dibromide (12)-(16) and (aryl)[N-(2-pyridyl)benzamido] (triphenylphosphine)nickel(II) (17)-(24), were synthesized and characterized.