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Silicon-containing Bis-Azomethines: Synthesis, Structural Characterization, Evaluation of the Photophysical Properties and Biological Activity

Silicon-containing Bis-Azomethines: Synthesis, Structural Characterization, Evaluation of the Photophysical Properties and Biological Activity

Mirela-Fernanada Zaltariov, Angelica Vlad, Maria Cazacu, Mihaela Avadanei, Nicoleta Vornicu, Mihaela Balan, Sergiu Shova

Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 5;138:38-48.

PMID: 25437843

Abstract:

A new diamine, (dimethylsilanediyl)bis(methylene)bis(4-aminobenzoate) (1), containing dimethylsilane spacer, was prepared by the condensation of p-aminobenzoic acid with bis(chloromethyl)dimethylsilane. This was subsequently reacted with salicylaldehyde, 3-hydroxy-salicylaldehyde, and 3-methoxy-salicyladehyde, when corresponding Schiff bases (E)-(dimethylsilanediyl)bis(methylene)bis(4-((E)-(2-hydroxybenzilidene)amino)benzoate (2), (E)-(dimethylsilanediyl)bis(methylene)bis(4-((E)-(2-hydroxybenzilidene)amino)benzoate (3), and (E)-(dimethylsilanediyl)bis(methylene) bis(4-((E)-(2-hydroxy-3-methoxybenzilidene)amino)benzoate (4), respectively were formed. All the obtained compounds were structurally characterized by spectral (FT-IR, (1)HNMR, (13)CNMR) analyses and single crystal X-ray diffraction. Photophysical studies revealed that the new prepared Schiff bases are good UV light absorbing and fluorescent materials. Thus, they exhibit strong UV/Vis-absorption at 250-400nm and violet or orange emission, in sensitive dependence on the polarity of the solvents and the nature of the substituent (H, OH and OCH3) at the aromatic ring. The antimicrobial activity of these compounds was first studied in vitro by the disk diffusion assay against two species of bacteria and three fungi. The minimum inhibitory concentration was then determined with the reference of standard compounds. The results displayed that Schiff bases 3 and 4 having hydroxy- and methoxy-substituents on the aromatic ring were better inhibitors of both types of species (bacteria and fungi) than standard compounds, Caspofungin and Kanamycin.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2917466	Bis(chloromethyl)dimethylsilane		2917-46-6	Price

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