100628-08-8Relevant academic research and scientific papers
Method for preparing chlorinated-3-substituted-2,5-diphenyl tetrazole under catalysis of copper Lewis acid surfactant
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Paragraph 0081; 0082; 0083; 0088; 0089, (2018/09/12)
The invention belongs to the technical field of organic synthesis and specifically relates to a method for preparing chlorinated-3-substituted-2,5-diphenyl tetrazole under the catalysis of a copper Lewis acid surfactant. The method comprises the following steps: 1) reacting benzaldehyde, phenylhydrazine, arylamine and sodium nitrite in solvent water by taking a copper Lewis acid surfactant Cu(OSO2CnH2n+1)2 as a catalyst to obtain 3-aryl-2,5-diphenylformazan; and 2) cyclizing and chlorinating 3-aryl-2,5-diphenylformazan in a mixed solvent of dichloromethane and water under the condition of a solid chlorination reagent N-chlorosuccinimide to obtain chlorinated-3-substituted-2,5-diphenyl tetrazole. By using the method, three-step conversion is completed according to a ''one-pot method'' continuous strategy, not only is an intermediate separation step omitted, but also the purification step is simple as well as convenient and easy to operate.
Anti-Plasmodium activity of tetrazolium salts
Cui, Xilin,Vlahakis, Jason Z.,Crandall, Ian E.,Szarek, Walter A.
, p. 1927 - 1947 (2008/09/21)
We have previously reported that sulfated cyclodextrins inhibit the invasion of Plasmodium merozoites by interacting with receptors present on the surface of erythrocytes. The observation that tetrazolium salts formed stable complexes with the inhibitory sulfated cyclodextrins suggested that tetrazolium salts might have anti-Plasmodium activity as well. Evaluation of commercially available tetrazolium salts indicated that some were active in the low nanomolar range and showed specificity in their inhibition of Plasmodium. Synthesis of a further 54 structures allowed us to determine that activity results from an aromatic component attached to the tetrazolium carbon atom (R1) and its size is not critical to the activity of the compound. Nitro modifications of active compounds are poorly tolerated, however, the presence of halogen atoms on aromatic groups attached to the nitrogen atoms of the tetrazolium ring (R2 and R3) has little effect on activity. Methoxy groups are tolerated on R2 and R3 components; however, they are disruptive on the R1 component. The overall results suggest that the R1 component is interacting with a specific hydrophobic environment and the R2 and R3 components are less constrained. The activity of these compounds in several human and mouse Plasmodium cultures suggests that the compounds interact with a component of the parasite that is both essential and conserved.
