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| Title: | Synthesis and leishmanicidal evaluation of sulfanyl‐and sulfonyl‐tethered functionalized benzoate derivatives featuring a nitroimidazole moiety |
| Authors: | Rodríguez, Miguel
Gutiérrez, Joyce
Domínguez, José
Peixoto, Philippe A.
Fernández, Alexis
Rodríguez, Noris
Deffieux, Denis
Rojas, Luis
Quideau, Stéphane
Pouységu, Laurent
Charris, Jaime |
| Keywords: | Nitroimidazole‐containing derivatives
Leishmania (V.) braziliensis
Leishmania (L.) mexicana
Antileishmanial activity
Catecholic derivative
Pyrogallolic derivative
Visceral leishmaniasis (VL)
Cutaneous leishmaniasis (CL)
Mucocutaneous leishmaniasis (MCL)
Pentavalent antimony compounds
Miltefosine
Nitroaromatic scaffolds
Metronidazole analogs
Synthesis
Nuclear magnetic resonance (NMR)
Infrared (IR)
Biological evaluation
LC50 values |
| Issue Date: | 16-Mar-2020 |
| Publisher: | DPhG Arch Pharm |
| Citation: | Micheel M. Vichi-Ramírez, Edgar López-López, Catalina Soriano-Correa, Carolina Barrientos-Salcedo, Using 5-Nitroimidazole Derivatives against Neglected Tropical Protozoan Diseases: Systematic Review, Future Pharmacology, 10.3390/futurepharmacol4010015, 4, 1, (222-255), (2024). Shweta Bisht, Lalan Kumar, Grace Kaul, Abdul Akhir, Deepanshi Saxena, Sidharth Chopra, R. Karthik, Neena Goyal, Sanjay Batra, Synthesis and Biological Evaluation of Substituted 3‐Isoxazolethioethers as Antileishmanial and Antibacterial Agents, ChemistrySelect, 10.1002/slct.202201664, 7, 25, (2022). Dinesh S. Reddy, Anamika Sinha, Amit Kumar, Vipin K. Saini, Drug re‐engineering and repurposing: A significant and rapid approach to tuberculosis drug discovery, Archiv der Pharmazie, 10.1002/ardp.202200214, 355, 11, (2022). Wilmer Alcazar, Sami Alakurtti, Maritza Padrón-Nieves, Maija Liisa Tuononen, Noris Rodríguez, Jari Yli-Kauhaluoma, Alicia Ponte-Sucre, Leishmanicidal Activity of Betulin Derivatives in Leishmania amazonensis; Effect on Plasma and Mitochondrial Membrane Potential, and Macrophage Nitric Oxide and Superoxide Production, Microorganisms, 10.3390/microorganisms9020320, 9, 2, (320), (2021). Om P.S. Patel, Omobolanle Janet Jesumoroti, Lesetja J. Legoabe, Richard M. Beteck, Metronidazole-conjugates: A comprehensive review of recent developments towards synthesis and medicinal perspective, European Journal of Medicinal Chemistry, 10.1016/j.ejmech.2020.112994, 210, (112994), (2021). |
| Abstract: | A series of new nitroimidazole-containing derivatives was synthesized by coupling of 2-[2-(2-methyl-5-nitro-1H-imidazol-1- l)ethylthio]ethanol with diversely substituted benzoic acids. Upon treatment with m-CPBA, 12 of these sulfanyl compounds were further oxidized to their sulfonyl analogs. All the 26 synthetic compounds were examined for in vitro activity against Leishmania (V.) braziliensis and Leishmania (L.) mexicana, and some of them displayed an efficient antileishmanial activity. Among the compounds tested, the catecholic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4-dihydroxybenzoate (9a, LC50 = 13 and 11 µM) and the pyrogallolic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4,5-trihydroxybenzoate (9b, LC50 = 4 and 1 µM) were the most active ones against the two Leishmania strains. |
| URI: | http://hdl.handle.net/10872/23246 |
| ISSN: | 0365-6233 |
| Appears in Collections: | Artículos Publicados
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