19765-08-3

Upstream product

• 696-23-1 2-methyl-5-nitro-1H-imidazole 
• 107-14-2 chloroacetonitrile 
• 696-23-1 2-methyl-4-nitro-1H-imidazole 

Relevant academic research and scientific papers

Synthesis, antifungal evaluation and molecular docking studies of some tetrazole derivatives

A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diamin-obenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.

Discovery of natural berberine-derived nitroimidazoles as potentially multi-targeting agents against drug-resistant Escherichia coli

A series of natural berberine-derived nitroimidazoles as novel antibacterial agents were designed, synthesized and characterized by nuclear magnetic resonance (NMR), infrared spectra (IR), and high resolution mass spectra (HRMS) spectra. The antimicrobial evaluation showed that some target molecules exhibited moderate to good inhibitory activities against the tested bacteria and fungi including clinical drug-resistant strains isolated from infected patients. Especially, 2-fluorobenzyl derivative 8f not only gave strong activity against drug-resistant E. coli with the minimal inhibitory concentration (MIC) value of 0.003 mM, 33-fold more active than norfloxacin, but also exhibited low toxicity toward RAW 264.7 cells and less propensity to trigger resistance. The aqueous solubility and ClogP values of target compounds were investigated to elucidate the structureactivity relationships. Molecular docking and quantum chemical studies for compound 8f rationally explained its antibacterial effect. The further exploration of antibacterial mechanism revealed that the highly active compound 8f could effectively permeabilize E. coli cell membrane and intercalate into DNA isolated from resistant E. coli to form 8f-DNA complex that might block DNA replication to exert the powerful bioactivities. Compound 8f could also selectively address resistant E. coli from a mixture of various strains.

Tetrahydro berberine nitro imidazole compounds and its preparation method and application (by machine translation)

The invention relates to a four-hydrogen berberine nitro imidazole compounds and its preparation method and application, four hydrogen berberine nitro imidazole compound as shown in formula I, the compound gram, gram-negative bacteria and fungi have certain inhibitory activity, can be used for preparing the anti-bacterial and/or antifungal drug, also can selectively inhibit the compound bacteria and/or fungi in particular the growth of bacteria, used for preparing microbial screening agent, may also be embedded DNA, as DNA embedded agent, and the preparation is simple in raw material, cheap and easy to obtain, short synthetic route, the application of the infection in the confrontation of great significance. (by machine translation)

An efficient protocol for facile synthesis of new 5-substituted-1H-tetrazole derivatives using copper-doped silica cuprous sulfate (CDSCS) as heterogeneous nano-catalyst

A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93percent). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.

Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1H-Tetrazole Derivatives Tethered to Bioactive N-Heterocyclic Cores

A series of new 5-substituted 1H-tetrazoles bearing bioactive N-heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as a heterogeneous nanocatalyst in water/i-PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount was discussed. This current protocol has many advantages including inexpensiveness, environmentally benign, broad substrate scope, excellent yields, and easy work-up procedure. The Cu/AC/r-GO used in this protocol is a low-cost catalyst that proved to have considerable chemical and thermal stabilities. This non-hygroscopic catalyst can be easily recycled, reused, and stored for many consecutive reaction runs without significant loss in its reactivity.