Síntesis y caracterización cristalográfica de 8-nitro y 5-nitro-2-(4´-nitrofenil) lepidinas con potencial actividad biológica
Durante décadas el estudio de los compuestos quinolínicos ha tenido gran relevancia debido a su presencia en una gran variedad de compuestos naturales y a su potencial actividad biológica; de ellos, los compuestos nitroquinolínicos han sido de gran interés debido a su promisoria actividad farmacológ...
- Autores:
-
Villamizar Caballero, Claudia Patricia
- Tipo de recurso:
- http://purl.org/coar/version/c_b1a7d7d4d402bcce
- Fecha de publicación:
- 2016
- Institución:
- Universidad Industrial de Santander
- Repositorio:
- Repositorio UIS
- Idioma:
- spa
- OAI Identifier:
- oai:noesis.uis.edu.co:20.500.14071/34962
- Palabra clave:
- Quinolinas
Compuestos Nitroquinolínicos
Monocristales
Quinolinic compounds have been from decades of high relevance due to their presence in several natural compounds and to their potential biological activity; from them
nitroquinolinic compounds have been of high interest due to their promising pharmacological activity
mainly as anti-parasitic compounds
as leishmanicidals and as antibacterials. 8-Nitro-2-(4’-nitrophenyl) lepidine and 6-methyl-5-nitro-2-(4’-nitrophenyl) lepidine were prepared through a Friedel-Crafts cyclization reaction of N-(α-allylbenzyl)anilines
aromatization through oxidation with melted sulfur (S8) and a nitration reaction to obtain the corresponding nitro lepidines. The two products were crystallized from proper solvent mixtures of ethyl acetate / n-heptane and good monocrystals were obtained
which were characterized by FT-IR
1 H and 13C-NMR and XRD of monocrystals. Crystalline products were also subjected to thermogravimetric (TGA) and differential scanning calorimetry (DSC) analyses. Using 2-phenyl lepidine and 2-phenyl-6-methyl lepidine as model substrates for an electrophilic aromatic nitration
Mulliken charges were calculated as well as their HOMO-LUMO orbital energy
with values that were correlated with those products analysed by RXD of monocrystals; XRD data accurately confirmed double nitration of lepidinas
showing for 8-nitro-2-(4’-nitrophenyl) lepidine that they are 16 molecules in the unit cell
in an orthorhombic system with spatial group Pbca (No. 16). For 6-methyl-5-nitro-2-(4’-nitrophenyl) lepidine it was determined that there are 8 molecules in the unit cell
in a monoclinic system with a spatial group P21/n (No. 14).
- Rights
- License
- Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)