100381-49-5Relevant articles and documents
Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity
Adardour, Mohamed,Boutafda, Aziz,Hdoufane, Ismail,Aghraz, Abdellah,Hafidi, Mohamed,Zaballos-García, Elena,Cherqaoui, Driss,Baouid, Abdesselam
, p. 3490 - 3506 (2020)
In this study, a novel series of 1,2,3-triazolyl-benzimidazolone derivatives have been synthesized by click reaction of azides with benzimidazolones 2a–b. The latter compounds were prepared with excellent yields (85–97%), the structures of products were determined by spectral analysis. Then, the X-rays crystallographic analysis of compound 7a revealed the self-assembling properties. The new heterocycles were evaluated for their in?vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and against fungi strains. The most tested synthesized compounds showed potent antibacterial and antifungal activities against all tested strains. The compound 6c was found to be the most active, particularly, against Aspergillus niger and Penicillium sp. with the same MIC and MBC of 0.0625 mg/mL. Furthermore, in silico molecular docking studies stipulated a sign of a good correlation between experimental activity and calculated binding affinity. According to the docking results, compound 6d showed minimum binding energy and can be considered as a good antimicrobial agent.
Microwave-assisted domino benzannulation of α-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones
Castillo, Juan-Carlos,Presset, Marc,Abonia, Rodrigo,Coquerel, Yoann,Rodriguez, Jean
experimental part, p. 2338 - 2345 (2012/05/19)
The microwave irradiation of a series of 2-diazo-1,3-diketones in the presence of an o-phenylenediamine derivative triggered a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence to provide a new synthetic entry to 1,3-dihydr-2H-1,5-benzodiazepin-2-ones, a class of molecules with important biological properties. The microwave-assisted reactions of 2-diazo-1,3-diones and o-phenylenediamines in the absence of additives furnished bi-and tricyclic 1,3-dihydro-2H-1,5-benzodiazepin-2-ones by a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence with the formation of three new covalent bonds. This reaction is a new and complementary synthetic approach to a class of "drug-like" compounds.