Recent Advances in The Chemistry and Biological Activity of Sulfonamide Derivatives

This review describes different synthetic methods for the preparation of sulfonamides. Generally, sulfonamides are synthesized from sulfonyl chloride derivative and amino derivative. A series of sulfonamide derivatives 7a-c, 8a,b, 9, 10, 11a,b, 12 were synthesized in alkaline media by reaction of different amino compounds with p-toluene sulfonyl chloride. Different amino derivatives 13, 15, 17, 19, 21 react with p-tolyl sulphonylchloride to afford sulfonylamides 14, 16, 18, 20, 22. Different reactions of sulfonamide derivatives have been summarized. Generally, sulfonamide function group does not take part in any reactions, but there are other functional groups in the compound which make the reactions. Sulfonamides have different biological activities e.g. antibacterial activity, anticancer activity, urease inhibitory activity, radical scavenging activity, carbonic anhydrase inhibitor, non-competitive inhibitor of lactoperoxidase, antifungal activity, and anti-mycobacterial activity.

METHOD FOR THE PREPARATION OF 2,4,6-TRIHYDROXYTOLUENE FROM 2,4,6-TRINITROTOLUENE

Статья посвящена усовершенствованию способа получения 2,4,6-тригидрокситолуола, востребованного химического реагента в синтезе азокрасителей и пигментов, а также химико-фармацевтических препаратов и различных полимеров. Основным сырьем для его получения является 2,4,6-тринитротолуол, который подвергают каталитическому гидрированию с последующим гидролизом образовавшегося 2,4,6-триаминотолуола. В данной работе предложены условия многоциклового использования палладиевого катализатора гидрирования 2,4,6-тринитротолуола, позволяющие сохранять активность катализатора и повысить выход 2,4,6-триаминотолуола выше 98 %. Аминопроизводное выделяется в виде дисульфата действием концентрированной серной кислоты. Кроме того, изучено влияние соотношения вода/дисульфат 2,4,6-триаминотолуола на выход 2,4,6-тригидрокситолуола; найдены условия, в которых выход на стадии гидролиза увеличен до 83-84 %. Проведен сравнительный анализ различных способов выделения 2,4,6-тригидрокситолуола из реакционной массы. The paper is concerned with upgrading the synthetic method for 2,4,6-trihydroxytoluene, an in-demand chemical reactant in the synthesis of azo-dyes and pigments, as well as chemical pharmaceuticals and various polymers. The basic feedstock for the synthesis thereof is 2,4,6-trinitrotoluene, which is subjected to catalytic hydrogenation followed by hydrolysis of the resulting 2,4,6-triaminotoluene. Here we suggest conditions for the multicycle use of Pd catalyst employed for the hydrogenation of 2,4,6-trinitrotoluene, which allow the catalyst activity to be retained and the yield of 2,4,6-triaminotoluene to be enhanced above 98%. The amino derivative is liberated as the disulfate by concentrated sulfuric acid. Moreover, we examined how the ratio of water / 2,4,6-triaminotoluene disulfate influences the yield of 2,4,6-trihydroxytoluene. Conditions were found in which the yield from hydrolysis is 83-84 %. Different methods for the isolation of 2,4,6-trihydroxytoluene from the reaction mixture were comparatively analyzed.

In silico and multi-spectroscopic analyses on the interaction of 5-amino-8-hydroxyquinoline and bovine serum albumin as a potential anticancer agent

Abstract5-Amino-8-hydroxyquinoline (5A8HQ), an amino derivative of 8-hydroxyquinoline, has become a potential anticancer candidate because of its promising proteasome inhibitory activity to overcome and yet synergize bortezomib for fighting cancers. Therefore, in this study, its physicochemical properties and interaction activities with serum protein have extensively been elucidated by both in vitro and in silico approaches to fulfill the pharmacokinetic and pharmacodynamic gaps. 5A8HQ exhibited the drug-likeness properties, where oral administration seems to be a route of choice owing to its high-water solubility and intestinal absorptivity. Multi-spectroscopic investigations suggested that 5A8HQ tended to associate with bovine serum albumin (BSA), a representative of serum protein, via the ground-state complexation. It apparently bound in a protein cleft between subdomains IIA and IIIA of BSA as suggested by the molecular docking and molecular dynamics simulations. The binding was mainly driven by hydrogen bonding and electrostatic interactions with a moderate binding constant at 104 M−1, conforming with the predicted free fraction in serum at 0.484. Therefore, 5A8HQ seems to display a good bioavailability in plasma to reach target sites and exerts its potent pharmacological activity. Likewise, serum albumin is a good candidate to be reservoir and transporter of 5A8HQ in the circulatory system.

Nanoscale materials in the composition of biosensors for the determination of amitriptyline

Biosensor devices including hybrid nanostructures as modifiers of transducer surfaces meet current requirements for the methods of research and determination of drugs, including antidepressants. The fea­tures of amperometric monoamine oxidase biosensors based on printed carbon electrodes modified with nanocomposite compositions C60 / cobalt nanoparticles/amino derivative of polyether polyol of the second generation/chitosan nanocomposite structures used for the detection of tricyclic antidepressant amitriptyline are considered. The choice of the best modifier was made proceeding from the data of transmission electron microscopy, scanning electron microscopy, electrochemical impedance spectroscopy, and differential pulse voltammetry. When developing the biosensor, conditions for depositing the composite composition of cobalt nanoparticles/amino derivative of polyether polyol on the electrode surface were varied: electrochemical deposition, sequential layer-by-layer deposition, and deposition of the mixture. The peak of electrochemical oxidation of hydrogen peroxide, which is formed during the enzymatic reaction of serotonin oxidation under the action of monoamine oxidase was used as an analytical signal of the biosensor. The principle of the biosensor action is based on the inhibitory effect of amitriptyline on the catalytic activity of immobilized monoamine oxidase. The proper choice of a modifier and optimal working conditions provided the range of detectable concentrations of amitriptyline: 1 x 10-4 - 1 x 10-8 M, the lower limit of the determined content at a level of 5 x 10-9 M for monoamine oxidase biosensor. Comparison of the results on the amitriptyline content determination in the pharmaceutical preparation and urine obtained using the monoamine oxidase biosensor and polarization fluorescence immunoassay (dilution of the tracer 1:32, dilution of antibodies 1:128, the range of working concentrations 5 x 10 -8 — 5 x 10-9 M), well-proven in the quantitative determination of medicinal substance, confirmed the correctness of the results obtained.

The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study

Herein, we report on the reaction of nitro-substituted azidobenzofuroxans with 1,3-dicarbonyl compounds in basic media. The known reactions of benzofuroxans and azidofuroxans with 1,3-dicarbonyl compounds in the presence of bases are the 1,3-dipolar cycloaddition and the Beirut reaction. In contrast with this, azidonitrobenzofuroxan reacts with 1,3-carbonyl compounds through Regitz diazo transfer, which is the first example of this type of reaction for furoxan derivatives. This difference is seemingly due to the strong electron-withdrawing effect of the superelectrophilic azidonitrobenzofuroxan, which serves as the azido transfer agent rather than 1,3-dipole in this case.

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Herein we report the synthesis and characterization of a new series of styryl-based push-pull dyes containing a free amino group and their Schiff base derivatives. The dyes include the dicyanomethylene group as an acceptor and different para-substituted alkylamines as donors. Morever as a proton-sensitive group a pyridin-2-yl substituent was attached to the para-position of the phenyl moiety in both series of compounds. The photophysical properties of the dyes were examined in various solvents with different polarities and showed absorption in the visible region and green-red emission with low quantum yields. The absorption and the emission maxima were shifted bathocromically by increasing the solvent’s polarity. However, there was no correlation with the polarity parameters of the solvents. The pH-sensitive properties of all prepared Schiff bases were examined against TBAOH in DMSO, via deprotonation of the OH group in the salicylidene moiety and their reverse protonation was also investigated using TFA. The Schiff bases exhibited a bathochromic shift upon the addition of TBAOH to their solutions in DMSO. Therefore, they showed potential to be utilized as colorimetric and luminescence pH sensors. The second-order nonlinear optical (NLO) responses of the dyes were measured by the electric field-induced second harmonic (EFISH) generation method. The highest μβ values were obtained for the dyes bearing the julolidine donor as 1430 × 10−48 esu (for free amino derivative) and 1950 × 10−48 esu (for Schiff base derivative), respectively. The structural and electronic properties of the dyes as well as their NLO properties were further studied using DFT calculations. The thermal stabilities of all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C.

Can Metal Organic Frameworks Outperform Adsorptive Removal of Harmful Phenolic Compound 2-Chlorophenol by Activated Carbon?

<b>Abstract:</b> Removal of persistent organic compounds from aqueous solutions is generally achieved using adsorbent like activated carbon (AC) but it suffers from limited adsorption capacity due to low surface area. This paper describes a pioneering work on the adsorption of an organic pollutant, 2-chlorophenol (2-CP) by two MOFs with high surface area and water stability; MIL-101 and its amino-derivative, MIL-101-NH₂. Although MOFs have higher surface area than AC, the latter was proven better having the highest equilibrium 2-CP uptake (345 mg.g^-1), followed by MIL-101 (121 mg.g^-1) and MIL-101-NH₂ (84 mg.g^-1). Used MIL-101 could be easily regenerated multiple times by washing with ethanol and even showed improved adsorption capacity after each washing cycle. These results can open the doors to meticulous adsorbent selection for treating 2-CP-contaminated water

Can Metal Organic Frameworks Outperform Adsorptive Removal of Harmful Phenolic Compound 2-Chlorophenol by Activated Carbon?

<b>Abstract:</b> Removal of persistent organic compounds from aqueous solutions is generally achieved using adsorbent like activated carbon (AC) but it suffers from limited adsorption capacity due to low surface area. This paper describes a pioneering work on the adsorption of an organic pollutant, 2-chlorophenol (2-CP) by two MOFs with high surface area and water stability; MIL-101 and its amino-derivative, MIL-101-NH₂. Although MOFs have higher surface area than AC, the latter was proven better having the highest equilibrium 2-CP uptake (345 mg.g^-1), followed by MIL-101 (121 mg.g^-1) and MIL-101-NH₂ (84 mg.g^-1). Used MIL-101 could be easily regenerated multiple times by washing with ethanol and even showed improved adsorption capacity after each washing cycle. These results can open the doors to meticulous adsorbent selection for treating 2-CP-contaminated water