Synthesis of novel 2H-indazole analogues via the Davis-Beirut reaction and conjugation onto magnetic nanoparticles
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Elsevier Ltd
Abstract
Methods for the construction of C3-amino substituted 2H-indazole motifs are scarce. While the Davis-Beirut reaction proved useful and versatile in the construction of alkoxy- and thia- C3-substituted 2H-indazoles under mild basic conditions, the same success was not enjoyed when confronted with nitrogen-based nucleophiles. Therefore, we set out to expand the scope of the Davis-Beirut reaction and investigated the ability of amine nucleophiles to prompt the heterocyclization. In addition, a model 2H-indazole analogue was successfully conjugated onto magnetic nanoparticles for the first time. The toxicity of the synthesized analogues was estimated using in silico T.E.S.T software. This report provides a reliable approach for the synthesis of indazole-loaded nanoparticles whose applications have not been investigated before. © 2017 Elsevier Ltd
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2h-indazoles, Davis-beirut reaction, Hyaluronic acid, In silico toxicity, Iron oxide nanoparticles, Benzylamine derivative, Indazole derivative, N (6 methoxy benzothiazol 2 yl) 5 bromo 2 nitrobenzylidene amine, N (6 methoxybenzothiazol 2 yl) 2 nitrobenzylamine, N (6 methoxybenzothiazol 2 yl) 2 nitrobenzylidene amine, N (6 methoxybenzothiazol 2 yl) 4 dimethylamino 2 nitrobenzylamine, N (6 methoxybenzothiazol 2 yl) 4 fluoro 2 nitrobenzylamine, N (6 methoxybenzothiazol 2 yl) 4 fluoro 2 nitrobenzylidene amine, N (6 methoxybenzothiazol 2 yl) 5 bromo 2 nitrobenzylamine, N (6 methoxybenzothiazol 2 yl) 5 chloro 2 nitrobenzylamine, N (6 methoxybenzothiazol 2 yl) 5 chloro 2 nitrobenzylidene amine, N 1 [2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]ethane 1,2 diamine, N 1 [2 [6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]ethane 1,2 diamine, N [2 [2 (2 aminoethoxy)ethoxy]ethyl] 2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 2 amine, N [2 [2 (2 aminoethoxy)ethoxy]ethyl] 4 fluoro 2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 amine, Tert butyl(2 [[2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]amino]ethyl]carbamic acid, Tert butyl[2 [(4 fluoro 2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]amino]ethyl]carbamic acid, Tert butyl[2 [2 [2 [[2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3yl]amino]ethyl]carbamic acid, Tert butyl[2 [[5 bromo 2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]amino]ethyl]carbamic acid, Tert butyl[2 [[5 chloro 2 (6 methoxybenzo[d]thiazol 2 yl) 2h indazol 3 yl]amino]ethyl]carbamic acid, Ultrasmall superparamagnetic iron oxide, Unclassified drug, Animal experiment, Article, Computer model, Controlled study, Developmental toxicity, Drug conjugation, Drug screening, Drug structure, Drug synthesis, Hydrodynamics, Lethal dose, Nonhuman, Prediction, Priority journal, Rat, Substitution reaction