Synthesis, structure and toxicity evaluation of ethanolamine nitro/chloronitrobenzoates: a combined experimental and theoretical study

Abstract

BackgroundNitroaromatic and chloronitroaromatic compounds have been a subject of great interest in industry and recently in medical-pharmaceutic field. 2-Chloro-4-nitro/2-chloro-5-nitrobenzoic acids and 4-nitrobenzoic acid are promising new agents for the treatment of main infectious killing diseases in the world: immunodeficiency diseases and tuberculosis.ResultsNew ethanolamine nitro/chloronitrobenzoates were synthesized and characterized by X-ray crystallography, UV–vis, FT-IR and elementary analysis techniques. The toxicity of the compounds prepared and correspondent components was evaluated using Hydractinia echinata as test system. A significant lower toxicity was observed for nitro-derivative compared with chloronitro-derivatives and individual components. Crystallographic studies, together with the chemical reactivity and stability profiles resulted from density functional theory and ab initio molecular orbital calculations, explain the particular behavior of ethanolamine 4-nitrobenzoate in biological test.ConclusionsThe experimental and theoretical data reveal the potential of these compounds to contribute to the design of new active pharmaceutical ingredients with lower toxicity.Electronic supplementary materialThe online version of this article (10.1186/s13065-017-0346-5) contains supplementary material, which is available to authorized users.

p-Aminobenzoate Organic Salts as Potential Plant Growth Regulators for Tomatoes

“…Our previous studies show the huge potential of alkanolamine-substituted benzoic acid systems which can generate supramolecular architectures with different topologies (1D, 2D and 3D) guided by different non-covalent interactions [23][24][25], have low toxicity [25,26], thermal stability [27] and promising applicability as auxin-like PGRs on the model plant Arabidopsis thaliana Col 0 [6]. The aim of this work was to develop new alkanolammonium p-aminobenzoates with characteristics of ideal PGRs: low toxicity, easily synthesized in laboratories, non-expensive, soluble in water and to investigate their role in growth and development of the most important vegetable cultivated in Romania and European Union in the last years, Solanum lycopersicum L. The discovery of new PGRs for commercial vegetables is essential, because vegetables play a vital role in food front, being the cheapest natural sources.…”

Investigating the Corrosion Inhibition Mechanisms of Alkanolammonium Salts: A Case Study with Ethylethanolammonium 4-Nitrobenzoate on Carbon Steel in Saline Solution

“…Specifically, our focus is on unraveling the intricate metal-inhibitor interactions and adsorption behavior in saline solutions. In line with our research group's dedication to investigating the structural properties of alkanolamine-substituted benzoic acid systems [23][24][25], recent findings predict the corrosion-inhibiting potential of ethylethanolammonium 4-nitrobenzoate (EEA4NB) on iron in a NaCl solution, shedding light on its thermal and kinetic behavior under non-isothermal and isothermal conditions [26]. The synthesized EEA4NB is now presented with a focus on its dual functionality, intervening in the control of both anodic and cathodic reactions while concurrently mitigating the aggressive impact of chloride on metal surfaces.…”

Bioprospecting Fluorescent Plant Growth Regulators from Arabidopsis to Vegetable Crops

“…Beside the presence of carboxylate and a planar aromatic ring, the substituent on the benzene ring exhibits an essential role in biological activity establishment. Our previous studies revealed the important role of different substituted benzoic acids in the synthesis of stable acid–base systems with supramolecular architectures guided by hydrogen bonding interactions [ 11 , 12 , 13 , 14 , 15 ], low toxicity [ 16 ] and promising plant growth regulatory activity on the model plant Arabidopsis ( Arabidopsis thaliana ) [ 17 , 18 ] and the vegetable crops cucumber ( Cucumis sativus ) [ 19 ] and tomato (Solanum lycopersicum ) [ 20 , 21 ].…”

“…The biological activities were analyzed and discussed as related to Arabidopsis model plant responses, the results being compared with our earlier research [ 18 ]. The new compounds with dual biological activity were obtained based on biologically active components (anion and cation) with well-known toxicological properties [ 16 ] or natural metabolites, accepted as safe compounds. p -Amino- and p -nitrobenzoic acids ( p ABAH, p NBAH) are commercially available reagents which received increasing attention as building blocks in drug development [ 29 , 30 ] as well as in plant science [ 18 , 21 ], p ABAH being a precursor of folic acid [ 31 ].…”