RESUMO
The benzazoles are very important entities having immense biological activities, hence; the synthesis of benzazoles is one of the prime areas for synthetic chemists. In pursuit of sustainable protocol, herein an oxidative enzyme i.e. catalase mediated sustainable synthesis is presented. Catalase is a metalloenzyme which is essential for the breakdown of toxic hydrogen peroxide into water and oxygen inside the cell. Despite the higher activity and turnover number of catalase inside the cell, its activity outside the cell is unexplored. Therefore, to explore the hidden potential of catalase for catalyzing the organic transformations, here we reported a green and efficient method for synthesis of benzazoles by the cyclocondensation of o-aminothiophenol or o-phenylenediammine and various aryl aldehydes with ensuing dehydrogenation. This protocol is greener, sustainable and rapid with excellent yields of the products and in addition to this, the catalase demonstrates good functional group tolerance.
Assuntos
Benzimidazóis/metabolismo , Benzotiazóis/metabolismo , Catalase/metabolismo , Compostos de Anilina/metabolismo , Benzimidazóis/química , Benzotiazóis/química , Biocatálise , Ciclização , Química Verde , Peróxido de Hidrogênio/metabolismo , Estrutura Molecular , Oxirredução , Fenilenodiaminas/metabolismo , Água/metabolismoRESUMO
New 2,4-thiazolidinediones with aryl sulfonylurea moieties have been synthesized by condensing various substituted sulfonamides and 5-(isocyanatomethyl) thiazolidino-2,4-dione. The isocyanomethyl thiazolidinedione was obtained by using the Curtius rearrangement, starting from known 2,4-dioxo-5-thiazolidineacetic acid. The newly synthesized compounds have been evaluated for the antihyperglycemic activity in normal rats model and among these compounds showed significant antihyperglycemic activity in sucrose loaded rat model.
Assuntos
Diabetes Mellitus/tratamento farmacológico , Hipoglicemiantes/farmacologia , Compostos de Sulfonilureia/química , Tiazolidinedionas/síntese química , Tiazolidinedionas/farmacologia , Animais , Glicemia/efeitos dos fármacos , Química Farmacêutica/métodos , Cromatografia em Camada Fina/métodos , Desenho de Fármacos , Masculino , Modelos Químicos , Ratos , Ratos Sprague-Dawley , Sacarose/química , Fatores de TempoRESUMO
A convenient and scalable four-step novel route has been developed for the synthesis of rosiglitazone (8), an antidiabetic drug. This multistep route requires 4-fluoro benzaldehyde (4), 2,4-thiazolidinedione (6) and 2-chloro pyridine (1) as key reactants and gives overall better yield of rosiglitazone. In addition, some steps have been accelerated, which leads to an overall time saving of 10h.
