55737-29-6Relevant articles and documents
Microwave assisted synthesis, biological activities, and in silico investigation of some benzimidazole derivatives
Bhavsar, Zeel A.,Acharya, Prachi T.,Jethava, Divya J.,Patel, Dhaval B.,Vasava, Mahesh S.,Rajani, Dhanji P.,Pithawala, Edwin,Patel, Hitesh D.
, p. 4215 - 4238 (2020)
Some derivatives of 2-substituted benzimidazole were prepared via coupling of N-methyl-o-phenylenediamine or o-phenylenediamine with different aromatic aldehydes catalyzed by Ni(OAc)2 in the presence of chloroform under microwave-assisted condi
Lowering the pKa of a bisimidazoline lead with halogen atoms results in improved activity and selectivity against Trypanosoma brucei in vitro
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)
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.
Novel approach to synthesis of substituted 3-aminoquinolines from nitroarenes and protected ethyl aminocrotonate
Bujok, Robert,Kwast, Andrzej,Cmoch, Piotr,Wróbel, Zbigniew
experimental part, p. 698 - 708 (2010/09/05)
The addition of mono- and dianions of ethyl N-pivaloyl-3-aminocrotonate to substituted nitroarenes, followed by action of silylating or acylating agent, leads to 3-aminoquinoline carboxylic acid derivatives. Hydrolysis and decarboxylation of the latter, carried out efficiently under relatively mild conditions, afford 3-aminoquinolines diversely substituted in the benzo-fused ring.