Synthesis of 3,4,5-trihydroxybenzohydrazone and evaluation of their urease inhibition potential

Taha, Muhammad; Khan, Ajmal; Arshad, Fiza; Ismail, Nor Hadiani; Afifi, Muhammad; Imran, Syahrul; Choudhary, M. Iqbal

doi:10.1016/j.arabjc.2015.06.036

Cited by 21 publications

(11 citation statements)

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“…In the continuation of our effort for enzyme inhibition [32–36], we have synthesized series of bisindole derivatives as a new class of anti-leishmanial agents. All compounds ( 1 – 27 ) were screened for their leishmanial activity (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, anti-leishmanial and molecular docking study of bis-indole derivatives

et al. 2019

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We have synthesized new series of bisindole analogs ( 1 – 27 ), characterized by 1 HNMR and HR-EI-MS and evaluated for their anti-leishmanial potential. All compounds showed outstanding inhibitory potential with IC 50 values ranging from 0.7 ± 0.01 to 13.30 ± 0.50 µM respectively when compared with standard pentamidine with IC 50 value of 7.20 ± 0.20 µM. All analogs showed greater potential than standard except 10 , 19 and 23 when compared with standard. Structure activity relationship has been also established for all compounds. Molecular docking studies were carried out to understand the binding interaction of active molecules. Electronic supplementary material The online version of this article (10.1186/s13065-019-0617-4) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Synthesis, anti-leishmanial and molecular docking study of bis-indole derivatives

et al. 2019

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“…(E)-3,4,5-trihydroxy-N'-(3-hydroxybenzylidene)benzohydrazide ( 20 ) ( Taha et al., 2019 ):- Yield (%): 54%; m.p. °C: 145–147; IR: 3465 (OH), 3340 (N-H), 1695 (C=O), 1616 (C=N),1460 (C=C Ar ring), 1318 (C-O), 1248 (N-N); 1 H-NMR (1:1 DMSO-d 6 /CDCl 3 , 400 MHz): δ 9.45–8.26 (m, 5H), 7.35–6.80 (m,7H); 13 C-NMR (1:1 DMSO-d 6 /CDCl 3 , 100 MHz): δ 166.7 (C=O), 161.4 (N=CH), 157.4 (C-O), 145.0 (C-O), 137.7 (C-O), 134.9 (C-O), 129.5 (CH), 120.1 (Ar C CH=N), 119.8 (CH), 118.5 (CH), 114.4 (Ar C -C=O), 109.0 (2xCH) ppm.…”

Section: Methodsmentioning

confidence: 99%

Preparation and biological assessment of some aromatic hydrazones derived from hydrazides of phenolic acids and aromatic aldehydes

Moussa

Al-Mamary

Al-Juhani

et al. 2020

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There has been substantial interest over the past many years in the design of novel chemical compounds containing the azomethine group (-NH-N=CH) and exhibiting various medicinal properties such as antibacterial, antiviral, antifungal, and anti-inflammatory activities. Herein, hydrazones were synthesized via the chemical reaction of substituted aromatic hydrazides with various aromatic aldehydes. The obtained products were confirmed using different physical and spectroscopic techniques, such as m.p., IR, 1 H-NMR and 13 C-NMR. The present study was designed to synthesize different aromatic hydrazones assembled by various combinations of aromatic hydrazides and aromatic benzaldehydes containing different substituents such as hydroxyl and polyhydroxyl groups as key structural features. Thus, incorporating such moieties and simultaneously creating highly-conjugated systems was expected to create novel species to mimic as much as possible natural phenolics, chalcones and stilbenes. Compounds of aromatic hydrazones synthesized in the present study were tested in vitro for their direct and indirect antioxidant activities using different methods such as DPPH, ABTS and FTC. The antioxidant activities of the new compounds ranged from very weak to very high activity. In addition, the inhibition of tyrosinase and cholinesterase by these compounds was tested. The new compounds containing two or three hydroxyl groups attached to aldehyde rings exhibited significantly greater inhibition effects on tyrosinase or cholinesterase activities in comparison to other compounds of the same series containing only one hydroxyl group.

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“…Due to the adverse effects of previously approved drugs, new AChE inhibitors are of great interest for the treatment of AD ( Kabir et al, 2021 ). Schiff bases are significant organic compounds involved in several biological activities like α-glucosidase, urease, β-glucuronidase, and antiglycation ( Khan et al, 2011 ; Taha et al, 2019a ; Taha et al, 2019b ).…”

Section: Introductionmentioning

confidence: 99%

2-Mercaptobenzimidazole clubbed hydrazone for Alzheimer’s therapy: In vitro, kinetic, in silico, and in vivo potentials

et al. 2022

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Alzheimer’s is a type of dementia that affects the affected person’s thinking, memory, and behavior. It is a multifactorial disease, developed by the breakdown of the neurotransmitter acetylcholine via acetylcholinesterase (AChE). The present study was designed to evaluate potential inhibitors of acetylcholinesterase that could be used as a therapeutic agent against Alzheimer’s disease (AD). For this course, synthetic compounds of the Schiff bases class of 2-mercaptobenzimidazole hydrazone derivatives (9–14) were determined to be potent acetylcholinesterase inhibitors with IC50 values varying between 37.64 ± 0.2 and 74.76 ± 0.3 μM. The kinetic studies showed that these are non-competitive inhibitors of AChE. Molecular docking studies revealed that all compounds accommodate well in the active site and are stabilized by hydrophobic interactions and hydrogen bonding. Molecular dynamics (MD) simulations of selected potent inhibitors confirm their stability in the active site of the enzyme. Moreover, all compounds showed antispasmodic and Ca2+ antagonistic activities. Among the selected compounds of 2-mercaptobenzimidazole hydrazone derivatives, compound 11 exhibited the highest activity on spontaneous and K+-induced contractions, followed by compound 13. Therefore, the Ca2+ antagonistic, AChE inhibition potential, and safety profile of these compounds in the human neutrophil viability assay make them potential drug candidates against AD in the future.

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Synthesis of 3,4,5-trihydroxybenzohydrazone and evaluation of their urease inhibition potential

Cited by 21 publications

References 50 publications

Synthesis, anti-leishmanial and molecular docking study of bis-indole derivatives

Synthesis, anti-leishmanial and molecular docking study of bis-indole derivatives

Preparation and biological assessment of some aromatic hydrazones derived from hydrazides of phenolic acids and aromatic aldehydes

2-Mercaptobenzimidazole clubbed hydrazone for Alzheimer’s therapy: In vitro, kinetic, in silico, and in vivo potentials

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