259816-68-7

Upstream product

• 24489-96-1 ethyl 3-(pyridin-4-yl)prop-2-enoate 
• 872-85-5 pyridine-4-carbaldehyde 
• 123293-78-7 ethyl 3-(4-pyridinyl)-(2E)-propenoate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 197774-66-6 ethyl 4-(4-pyridinyl)pyrrole-3-carboxylate 

Relevant academic research and scientific papers

Antimycobacterial Pyrroles: Synthesis, Anti-Mycobacterium tuberculosis Activity and QSAR Studies

A number of known antifungal pyrrole derivatives and some newly synthesized compounds (5-33) were tested in vitro against Mycobacterium tuberculosis CIP 103471. The majority of tested compounds were efficient antimycobacterial agents showing MIC values ranging from 0.5 to 32 μg/mL. A 3-D-QSAR study has been performed on these pyrrole derivatives to correlate their chemical structures with their observed inhibiting activity against M. tuberculosis. Due to the absence of information on a putative receptor responsible for this activity, classical quantitative structure-activity relationships (QSAR) and comparative molecular field analysis (CoMFA) have been applied. A model able to well correlate the antimycobacterial activity with the chemical structures of pyrrole derivatives 5-33 has been developed which is potentially helpful in the design of novel and more potent antituberculosis agents. The combination of CoMFA with classical QSAR descriptors led to a better hybrid 3-D-QSAR model, that successfully explains the structure-activity relationships (r2=0.86) of the training set. A comparison between the QSAR, CoMFA and mixed QSAR-CoMFA models is also presented. The hybrid model is to be preffered, however, because of its lowest values of the average absolute error of prediction toward a limited external test set.

Pyridinylpyrrolyl analogs of isoniazid: Synthesis and antimycobacterial activities

Pyridinylpyrrolyl analogs of isoniazid (INH) were prepared by reaction of ethyl 3-(4-pyridinyl)-2-propenoate with toluenesulfonylmethylisocyanide (TosMIC). The pyrrole esters which formed were reacted with hydrazine hydrate to afford INH analogs 7-10. These compounds and various related derivatives were tested against a number of mycobacteria in comparison with INH and streptomycin (SM). Although 4-(4-pyridinyl)pyrrole-3-carboxyhydrazide 34 was not active, some related derivatives showed interesting antitubercular activities. Among them, derivative 19 was the most potent both against M. tuberculosis (MIC = 1.47 μM) and M. avium (MIC = 4.40 μM), a non- tuberculous agent responsible of fatal infection in AIDS patients. Compounds 15 and 33 also were endowed with appreciable activities against M. tuberculosis and M. avium.