Incorporation of azo group at axial position of silatranes: synthesis,characterization and antimicrobial activity |
| |
| Authors: | Gurjaspreet Singh Amandeep Saroa Shally Girdhar Sunita Rani Duane Choquesillo‐Lazarte Subash Chandra Sahoo |
| |
| Affiliation: | 1. Department of Chemistry, Panjab University, Chandigarh, India;2. Laboratorio de Estudios Cristalográficos, IACT, CSIC‐University of Granada, Armilla (Granada), Spain |
| |
| Abstract: | 4‐Aminoazobenzene‐derived silatranes bearing urea and aminosuccinimide as linker groups at the axial position are reported. The urea functionality is introduced in a silane ( 2 ) by the rearrangement reaction between 3‐isocyanatopropyltriethoxysilane and 4‐aminoazobenzene. N‐(3‐silatranylpropyl)‐N′‐[(p‐phenyldiazenyl)phenyl]urea and N‐[3‐(3,7,10‐trimethylsilatranyl)propyl]‐N′‐[(p‐phenyldiazene)phenyl]urea were prepared by transesterification reaction of 2 with triethanolamine and trisisopropanolamine, respectively. An efficient method for C? N bond formation is described for the synthesis of 3‐(silatranylpropyl)amino‐N‐[(p‐phenyldiazene)phenyl]pyrrolidine‐2,5‐dione and 3‐[(3,7,10‐trimethylsilatranyl)propyl]amino‐N‐[(p‐phenyldiazene)phenyl]pyrrolidine‐2,5‐dione via aza‐Michael addition reaction of aminopropylsilatranes with 4‐(N‐maleimido)azobenzene under mild conditions. All the compounds were well characterized using elemental analysis, spectroscopic techniques, thermogravimetric analysis and X‐ray diffraction. UV–visible spectroscopy indicates that the 4‐aminoazobenzene‐derived silatranes are capable acetate receptors. The synthesized compounds were screened for possible antimicrobial properties with the results showing a modest activity. Copyright © 2015 John Wiley & Sons, Ltd. |
| |
| Keywords: | 4‐aminoazobenzene silatrane urea aminosuccinimide acetate receptor antimicrobial activity |
|
|
