Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted

Abstract

A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 μg/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme.

Synthesis, In Silico and Pharmacological Evaluation of New Thiazolidine-4-Carboxylic Acid Derivatives Against Ethanol-Induced Neurodegeneration and Memory Impairment

“…Catalase (CAT) is a common heme-containing enzyme that catalyzes the decomposition of H 2 O 2 to H 2 O. Catalase activity was measured by monitoring the decrease in absorbance due to decomposition of H 2 O 2 at 240 nm according to the previously reported method with minor modifications. 57 A reaction mixture consisting of 1.95 mL of PBS (pH 7.0), 1mL of hydrogen peroxide (H 2 O 2 ), and 0.05mL of supernatant was prepared, and the absorbance was measured at 240 nm. The results were expressed as µmoles of H 2 O 2 /min/mg of protein.…”

A Survey of Synthetic Routes and Antitumor Activities for Benzo[g]quinoxaline-5,10-diones

“…Kurban et al [ 34 ] synthesized (2-chloro-3-tolylamino)naphthalene-1,4-dione (X = H, R = 2- or 3-CH 3 ) from 2,3-dichloro-1,4-naphthoquinone 1 , which when reacted with sodium azide (NaN 3 ) in moist DMF, afforded 1- or 2-methylbenzo[ b ]phenazine-6,11-dione 15c or 15d as the only isolated products ( Scheme 7 ).…”

Normal phase thin layer chromatography for aromatic derivatives of 3-chloro-1,4-naphtochinone

“…Modification of 2,3-dichloro-1,4-naphthoquinone by amine-containing compounds by the nucleophilic substitution reaction of one of the chlorine atoms on the R-amine fragment has been known for a long time and is often used now [6]. Synthesis and study of the biological activity of 1,4-naphthoquinone derivatives continue [7][8][9][10][11].…”

“…10 (R f = 0.52), for which with increasing number of CH 2 groups there is an increase in R f , so in the NPC conditions according to [10] sorption decreases. Often in articles TLC conditions for 1,4naphthoquinone derivatives are not described, or for analytes used MP with the same components, but in different ratios and an example of such an approach to TLC can be [11], which describes the results of synthesis and study of antimicrobial properties and the ability to inhibit the activity of the catalase enzyme of many N-, S-, O-substituted derivatives of 1,4-naphtho-and bezoquinone. The aim of the researchers [11] was to select such a ratio between CHCl 3 and PE that R f were in the range of 0.4-0.6 and probably the reaction products were separated from the starting materials.…”