58755-70-7Relevant articles and documents
Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
supporting information, p. 4941 - 4948 (2019/11/03)
The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
Discovery of Marinoquinolines as Potent and Fast-Acting Plasmodium falciparum Inhibitors with in Vivo Activity
Aguiar, Anna Caroline Campos,Panciera, Michele,Simao Dos Santos, Eric Francisco,Singh, Maneesh Kumar,Garcia, Mariana Lopes,De Souza, Guilherme Eduardo,Nakabashi, Myna,Costa, José Luiz,Garcia, Célia R.S.,Oliva, Glaucius,Correia, Carlos Roque Duarte,Guido, Rafael Victorio Carvalho
, p. 5547 - 5568 (2018/06/18)
We report the discovery of marinoquinoline (3H-pyrrolo[2,3-c]quinoline) derivatives as new chemotypes with antiplasmodial activity. We evaluated their inhibitory activities against P. falciparum and conducted a structure-activity relationship study, focusing on improving their potency and maintaining low cytotoxicity. Next, we devised quantitative structure-activity relationship (QSAR) models, which we prospectively validated, to discover new analogues with enhanced potency. The most potent compound, 50 (IC503d7 = 39 nM; IC50K1 = 41 nM), is a fast-acting inhibitor with dual-stage (blood and liver) activity. The compound showed considerable selectivity (SI > 6410), an additive effect when administered in combination with artesunate, excellent tolerability in mice (all mice survived after an oral treatment with a 1000 mg/kg dose), and oral efficacy at 50 mg/kg in a mouse model of P. berghei malaria (62% reduction in parasitemia on day 5 postinfection); thus, compound 50 was considered a lead compound for the discovery of new antimalarial agents.
A new regiospecific synthesis method of 1H-pyrazolo[3,4-b]quinoxalines – Potential materials for organic optoelectronic devices, and a revision of an old scheme
Danel, Andrzej,Wojtasik, Katarzyna,Szlachcic, Pawe?,Gryl, Marlena,Stadnicka, Katarzyna
, p. 5072 - 5081 (2017/07/28)
A series of 6-substituted-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxalines were prepared using a new synthetic pathway: reductive cyclization of appropriate 5-(o-nitrophenyl)-pyrazoles with ferrous oxalate or triphenylphosphine. The main advantage of this procedure is that, contrary to the older protocols of pyrazolo[3,4-b]quinoxaline synthesis, this method allows for a substituent to be introduced to the carbocyclic ring without the formation of isomers. The pyrazole ring can also be modified to some extent. Furthermore, we propose a new mechanism for the oldest reported pyrazolo[3,4-b]quinoxaline synthesis, based on the condensation between o-phenylenediamine and 3,4-pyrazolin-5-diones.
