New 1-(3-nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines: synthesis and computational study
| Autor: | Romualdas Sirutkaitis, Zita Staniulytė, Algirdas Palaima, Antanas Karalius, Žilvinas Anusevičius, Lidija Kosychova, Audrius Laurynėnas |
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| Rok vydání: | 2015 |
| Předmět: |
Triazole
Pharmaceutical Science Ring (chemistry) Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Benzodiazepines five-membered fused heterocycles DFT local descriptors [1 2 4]triazolo[4 3-a][1 5]-benzodiazepine density functional theory (DFT) lcsh:Organic chemistry Computational chemistry Drug Discovery 3-nitrobenzohydrazide DFT global descriptors Reactivity (chemistry) Physical and Theoretical Chemistry quantum mechanical calculation Fukui index Spectral data Mechanical Phenomena chemistry.chemical_classification Molecular Structure Organic Chemistry Computational Biology [1 2 4]triazolo[4 3-a][1 5]-benzodiazepine five-membered Toluene chemistry Models Chemical Chemistry (miscellaneous) Cyclization Triazole derivatives Molecular Medicine Quantum Theory Density functional theory Tricyclic |
| Zdroj: | Molecules Volume 20 Issue 4 Pages 5392-5408 Molecules, Vol 20, Iss 4, Pp 5392-5408 (2015) Molecules, Basel : MDPIAG, 2015, Vol. 20, no. 4, p. 5392-5408 Molecules, Basel : MDPI, 2015, vol. 20, no. 4, p. 5392-5408 |
| ISSN: | 1420-3049 |
| Popis: | Triazole derivatives constitute an important group of heterocyclic compounds have have been the subject of extensive study in the recent past. These compounds have shown a wide range of biological and pharmacological activities. In this work, new fused tricyclic 1-(3-nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]-benzodiazepines have been synthesized by the thermal cyclization of N'-(2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-3- nitrobenzohydrazides. After screening ethanol, toluene and 1-butanol as solvents, butanol-1 was found to be the best choice for the cyclization reaction in order to obtain the highest yields of tricyclic derivatives. The chemical structures of the synthesized compounds were elucidated by the analysis of their IR, 1H- and 13C-NMR spectral data. For tentative rationalization of the reaction processes, the global and local reactivity indices of certain compounds, taking part in the reaction pathway, were assessed by means of quantum mechanical calculations using the conceptual density functional theory (DFT) approach. This work could be useful for the synthesis of new heterocyclic compounds bearing a fused triazole ring. |
| Databáze: | OpenAIRE |
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