74979-71-8Relevant academic research and scientific papers
Synthesis and in vitro evaluation of Ca2 + channel blockers 1,4-dihydropyridines analogues against Trypanosoma cruzi and Leishmania amazonensis: SAR analysis
Pollo, Luiz A.E.,de Moraes, Milene H.,Cisilotto, Júlia,Creczynski-Pasa, Tania B.,Biavatti, Maique W.,Steindel, Mario,Sandjo, Louis P.
, p. 789 - 797 (2017)
Drugs containing the1,4-dihydropyridine (DHP) core have recently attracted attention concerning their antiparasitic effect against various species of Leishmania and Trypanosoma. This approach named drugs repositioning led to interesting results, which have prompted us to prepare 21 DHP's analogues. The 1,4-DHP scaffold was decorated with different function groups at tree points including the nitrogen atom (NH and N-phenyl), the aryl group attached to C-4 (various substituted aryl residues) and the carbon atoms 2 and 6 (bearing Ph or Me groups). Moreover, the products were evaluated for their cytotoxicity on three cancer and a non-tumoral cell lines. Only 6 of them were antiproliferative and their weak effect (CC50 comprised between 27 and 98 μM) suggested these DHPs as good candidates against the intracellular amastigote forms of L. amazonensis and T. cruzi. L. amazonensis was sensitive to DHPs 5, 11 and 15 (IC50 values at 15.11, 45.70 and 53.13 μM, respectively) while 12 of them displayed significant to moderate trypanocidal activities against T. cruzi. The best trypanocidal activities were obtained with compounds 2, 18 and 21 showing IC50 values at 4.95, 5.44, and 6.64 μM, respectively. A part of the N-phenylated DHPs showed a better selectivity than their NH analogues towards THP-1 cells. 4-Chlorophenyl, 4-nitrophenyl and 3-nitrophenyl residues attached to the carbon atom 4 turned to be important sub-structures for the antitrypanosomal activity.
Search for Antimicrobial Activity Among Fifty-Two Natural and Synthetic Compounds Identifies Anthraquinone and Polyacetylene Classes That Inhibit Mycobacterium tuberculosis
Pollo, Luiz A. E.,Martin, Erlon F.,Machado, Vanessa R.,Cantillon, Daire,Wildner, Leticia Muraro,Bazzo, Maria Luiza,Waddell, Simon J.,Biavatti, Maique W.,Sandjo, Louis P.
, (2021/02/12)
Drug-resistant tuberculosis threatens to undermine global control programs by limiting treatment options. New antimicrobial drugs are required, derived from new chemical classes. Natural products offer extensive chemical diversity and inspiration for synthetic chemistry. Here, we isolate, synthesize and test a library of 52 natural and synthetic compounds for activity against Mycobacterium tuberculosis. We identify seven compounds as antimycobacterial, including the natural products isobavachalcone and isoneorautenol, and a synthetic chromene. The plant-derived secondary metabolite damnacanthal was the most active compound with the lowest minimum inhibitory concentration of 13.07 μg/mL and a favorable selectivity index value. Three synthetic polyacetylene compounds demonstrated antimycobacterial activity, with the lowest MIC of 17.88 μg/mL. These results suggest new avenues for drug discovery, expanding antimicrobial compound chemistries to novel anthraquinone and polyacetylene scaffolds in the search for new drugs to treat drug-resistant bacterial diseases.
1-ARYL- AND 1-BENZYL-3,5-DIETHOXYCARBONYL-1,4-DIHYDROPYRIDINES
Sausin, A.E.,Chekavichus, B.S.,Lusis, V.K.,Dubur, G.Ya.
, p. 377 - 385 (2007/10/02)
The possibility has been studied of using anilines in the Hantzsch synthesis.It has been shown that, with the exception of those containing strong electron-accepting substituents, they take part in this reaction with the formation of 1-aryl-1,4-dihydropyridines.The reaction largely depends on the nature of the substituents in the aniline and in the benzaldehyde and is promoted by electron-accepting substituents in the aldehyde and electron-donating substituents in the amine.The mechanism of the reaction is discussed.A number of 1-benzyl-1,4-dihydroxypyridines have been synthesized.The UV, IR, and PMR spectra and the electro-oxidation of the compounds obtained have been studied.
