Sulfonamide hybrid schiff bases of anthranilic acid: Synthesis, characterization and their biological potential

Kausar, Naghmana; Muratza, Shahzad; Raza, Muhammad Asam; Rafique, Hummera; Arshad, Muhammad Nadeem; Altaf, Ataf Ali; Asiri, Abdullah M.; Shafqat, Syed Salman; Shafqat, Syed Rizwan

doi:10.1016/j.molstruc.2019.02.056

Cited by 25 publications

(10 citation statements)

References 26 publications

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“…Antioxidant activity results were comparable with the compounds containing sulfur and benzimidazole groups. [ 18,19,28,29 ] Based on structural similarities of studied compounds to melatonin, hydrogen atom transfer (HAT) and single electron transfer (SET) are the main mechanisms expected to contribute to their free‐radicals scavenging activity. The SET mechanism for direct radical scavenging of melatonin is the most favorable mechanism in aqueous solution, while in nonpolar aprotic medium HAT is prevailing.…”

Section: Resultsmentioning

confidence: 99%

Antioxidant and DNA damage protecting activities of newly synthesized thiol bridged bis‐benzimidazole derivative and its dicationic analogue

Yıldız

2020

Journal of Heterocyclic Chem

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Two new types of bis‐benzimidazole derivatives containing thiol group have been prepared and characterized. The compounds contain sulfur with imidazole ring show promising biological activities such as antioxidant, anticancer, antimicrobial and etc. The aim of this study was synthesis of benzimidazole derivatives which not only show antioxidant activity but also protect DNA from oxidative damage. Antioxidant activities of the synthesized compounds were investigated with DPPH and hydrogen peroxide radical scavenging assays. DNA nicking assay was applied to establish activity of compounds to protect plasmid DNA from Fenton's reagent radicals. Both compounds had antioxidant activity, however, activity of dicationic analogue was greater than well‐known antioxidant Vit C. IC50 values calculated according to DPPH method were 14.5 μM for dicationic analogue (2) and 57.5 μM for 1,2‐bis(1‐methyl‐1H‐benzo[d]imidazol‐2‐ylthio)ethane (1). In hydrogen peroxide scavenge assay IC50 values of compounds were 638.6 μg/mL for 1,2‐bis(1‐methyl‐1H‐benzo[d]imidazol‐2‐ylthio)ethane (1), 398.9 μg/mL for dicationic analogue (2). Furthermore, dicationic analogue promised an effective DNA protection due to its positive charge interacting with negatively charged DNA. Also the high solubility of the dicationic analogue in water due to its positive charge could provide a great advantage in biological applications.

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Section: Resultsmentioning

confidence: 99%

Antioxidant and DNA damage protecting activities of newly synthesized thiol bridged bis‐benzimidazole derivative and its dicationic analogue

Yıldız

2020

Journal of Heterocyclic Chem

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“…An imine group (–RC = N–) containing Schiff bases are also used as dyes, intermediate reactants in the synthesis of organic compounds, catalysts, stabilizing agent in polymeric products, chelating agents in analytical separation methods and inhibitor of corrosion [ 10 , 11 ]. Moreover, Schiff bases possess noteworthy applications in multifaceted areas such in the solar cell, optical ingredients [ 6 , 7 , 9 , 12 ] and medication area such as antiviral, antifungal, antibacterial, insecticidal, anti-HIV, anticancer, antiprotozoal, antimalarial, anti-inflammatory, antidiabetic and antitumor [ 2 , 3 , 5 , 7 , 10 , 11 , 12 , 13 , 14 , 15 ]. From the point of view, we report herein the synthesis, characterization as well as investigation of in silico quantum calculations of the entitled SBDTC Schiff base in particulars.…”

Section: Introductionmentioning

confidence: 99%

Computational and experimental insight into antituberculosis agent, (E)-benzyl-2-(4-hydroxy-2-methoxybenzylidene) hydrazinecarbodithioate: ADME analysis

Pal

Mumit

Hossen

et al. 2021

Heliyon

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“…An imine group (-RC ¼ N-) containing Schiff bases are also used as dyes, intermediate reactants in the synthesis of organic compounds, catalysts, stabilizing agent in polymeric products, chelating agents in analytical separation methods and inhibitor of corrosion [10,11]. Moreover, Schiff bases possess noteworthy applications in multifaceted areas such in the solar cell, optical ingredients [6,7,9,12] and medication area such as antiviral, antifungal, antibacterial, insecticidal, anti-HIV, anticancer, antiprotozoal, antimalarial, anti-inflammatory, antidiabetic and antitumor [2,3,5,7,10,11,12,13,14,15]. From the point of view, we report herein the synthesis, characterization as well as investigation of in silico quantum calculations of the entitled SBDTC Schiff base in particulars.…”

Section: Introductionmentioning

confidence: 99%

Computational and Experimental Insight Into Antituberculosis Agent, (E)-Benzyl-2-(4- Hydroxy-2-Methoxybenzylidene) Hydrazinecarbodithioate: ADME Analysis

et al. 2021

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A new Schiff base, (E)-benzyl-2-(4-hydroxy-2-methoxybenzylidene)hydrazinecarbodithioate (compound 1) has been synthesized and experimentally characterized by the IR, UV-Vis, 1 H-NMR and mass spectroscopies. The theoretical study of the synthesized compound was evaluated using the density functional theory (DFT) at B3LYP/ 6-31Gþ(d,p) basis set. The electronic absorption spectrum of compound 1 was evaluated using time-dependent density functional theory. Besides, in silico studies were done for the prediction of absorption, distribution, metabolism and excretion profiles of compound 1. According to the result, the theoretical data were well fitted with the experimental values. The studied compound has low chemical reactivity and high kinetic stability. In the molecular electrostatic potential map, the negative and positive potential sites were found around electronegative atoms and hydrogen atoms of compound 1, respectively. The 97.75% Lewis and 2.25% non-Lewis structure were present in the studied molecule. The molecular docking results reveal that compound 1 can be used as antituberculosis agent as compare to ethambutol.

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Sulfonamide hybrid schiff bases of anthranilic acid: Synthesis, characterization and their biological potential

Cited by 25 publications

References 26 publications

Antioxidant and DNA damage protecting activities of newly synthesized thiol bridged bis‐benzimidazole derivative and its dicationic analogue

Antioxidant and DNA damage protecting activities of newly synthesized thiol bridged bis‐benzimidazole derivative and its dicationic analogue

Computational and experimental insight into antituberculosis agent, (E)-benzyl-2-(4-hydroxy-2-methoxybenzylidene) hydrazinecarbodithioate: ADME analysis

Computational and Experimental Insight Into Antituberculosis Agent, (E)-Benzyl-2-(4- Hydroxy-2-Methoxybenzylidene) Hydrazinecarbodithioate: ADME Analysis

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