Design, Synthesis and Activity Against Trypanosoma cruzi of Azaheterocyclic Analogs of Megazol
| Autor: | Nubia Boechat, Alcione S. Carvalho, Nelilma C. Romeiro, S. L. de Castro, Rubem Figueiredo Sadok Menna-Barreto |
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| Rok vydání: | 2007 |
| Předmět: |
Aza Compounds
Magnetic Resonance Spectroscopy biology Stereochemistry Trypanosoma cruzi Triazole Biological activity biology.organism_classification Ring (chemistry) Mass Spectrometry Megazol chemistry.chemical_compound Mechanism of action chemistry Design synthesis Heterocyclic Compounds Thiadiazoles Drug Discovery medicine Nitro Animals medicine.symptom |
| Zdroj: | Medicinal Chemistry. 3:460-465 |
| ISSN: | 1573-4064 |
| DOI: | 10.2174/157340607781745519 |
| Popis: | This study describes the design, synthesis and trypanocidal evaluation of new azaheterocyclic derivatives (4-8). These compounds were designed as megazol (1) analogs based on bioisosterism tools and were synthesized to investigate the possible pharmacophoric contribution of the 1,2,4-triazole nucleus, the position of the heterocyclic nucleus and presence of the nitro group, to the activity against the bloodstream trypomastigote forms of Trypanosoma cruzi. The most potent compound was 6, a nitro derivative obtained by substitution of a thiadiazole by a triazole ring and by moving the nitro group from C-5 position, as in 1, to the C-4 position. Finally, we have used semi-empirical theoretical calculations to discuss the correlation of some stereo electronic properties with biological activity in an attempt to understand the possible mechanism of action of the designed series of compounds. |
| Databáze: | OpenAIRE |
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