Here, we report for the first time the synthesis and the antileishmanial activity of a new pyrazole derivative, namely 4-[2-(1-(ethylamino)-2-methylpropyl)phenyl]-3-(4-methyphenyl)-1-phenylpyrazole). Micromolar concentrations of this compound were found to inhibit the in vitro multiplication of Leishmania tropica, Leishmania major, and Leishmania infantum, three species causing different forms of leishmaniasis. Furthermore, the 50% inhibitory concentration (IC50) values for the compound are only slightly higher than those of amphotericin B, one of the most active antileishmanial agents used as a satisfactory substitute in cases not responding to pentostam. The IC50 values after 48 h for L. tropica, L. major, and L. infantum promastigote growth were 0.48 microg/mL, 0.63 microg/mL and 0.40 microg/mL, respectively for the compound, while they were 0.23 microg/mL, 0.29 microg/mL and 0.24 microg/mL, respectively for amphotericin B. We also tested this compound for its antibacterial activity against several bacteria. The strongest antibacterial activity was observed against Entrococcus feacalis and Staphylococcus aureus with a minimal inhibitory concentration (MIC) of 60 microg/mL.
Diarylnitrilimine and arylnitriloxide dipoles react with two 8-hydroxyquinoline substrates to give respectively pyrazolinic and isoxazolinic derivatives. The structure of these new heterocycles was established on the basis of their spectroscopic data and by chemical methods. The inhibition activity of one of these heterocycles was evaluated in vitro against 8 pathogenic µ-organisms. J. Heterocyclic Chem., 40, 243 (2003).
Introduction.Although 8-hydroxyquinoline derivatives are endowed with some interesting biological properties [1], they are more often known as selective metal extractants [2]. In the course of the research completed in our respective laboratories for the development of heterocyclic compounds of both synthetic and biological interest [3], we report here about new polycyclic derivatives synthesized by 1,3-dipolar cycloadditions of diarylnitrilimines (DANI) and arylnitriloxides (ANO) with 7-(2'-propenyl)-8-hydroxyquinoline 2 and 7-(1'-propenyl)-8-hydroxyquinoline 3. -J AB = 13.4 J 5'-6' = 7.5 J 4'A-5' = 3.3 J 4'B-5' = 10.3 5b 3.63 2.75 (dd) 4.90 (m) 3.13 (d) 2.35 (s) 37.5 59.1 32.5 21.1 J AB = 13.3 J 5'-6' = 6.9 J 4'A-5' = 3.3 J 4'B-5' = 10.3 5c 3.62 2.72 (dd) 4.90 (m) 3.15 (d) 3.80 (s) 38.0 59.0 31.7 55.0 J AB = 13.1 J 5'-6' = 6.3 J 4'A-5' = 3.2 J 4'B-5' = 10.3 5d 3.62 2.75 (dd) 5.10 (m) 3.20 (d) -36.6 60.0 32.0 -J AB = 13.4 J 5'-6' = 7.6 J 4'A-5' = 3.1
Diarylnitrilimine and arylnitriloxide dipoles react with two 8-hydroxyquinoline substrates to give respectively pyrazolinic and isoxazolinic derivatives. The structure of these new heterocycles was established on the basis of their spectroscopic data and by chemical methods. The inhibition activity of one of these heterocycles was evaluated in vitro against 8 pathogenic µ-organisms.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.