Synthesis and pharmacological evaluation of schiff bases of 7-amino-4-methyl coumarins as novel anti-inflammatory agents

Krishna, R. Jaya; Pandagale, Abhishek; Ronad, Pradeepkumar; Honnalli, S.S.; Das, Bhrigu Kumar; Gadad, Pramod C.

doi:10.31024/ajpp.2019.5.4.7

Cited by 5 publications

(2 citation statements)

References 20 publications

(25 reference statements)

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“…In accordance with the literature, scopoletin and umbelliferone (which exhibit a dual inhibitory activity against COX-2 and 5-LO [100]) suppress the synthesis of inflammatory mediators (histamine and serotonin), pro-inflammatory cytokines (IL-1β, TNF-α), leukotrienes, and other biological substances, which decreases the microvasculature vessel permeability and prevents blood plasma exudation, local edema development, blood cell migration, and infiltrated cell development [88,89,[101][102][103]. In addition, coumarins reduce myeloperoxidase concentration and suppress neutrophil chemotaxis [92,104]. The reduced gastric mucosa inflammation is accompanied by an increase in somatostatin secretion and a reduction in gastrin secretion.…”

Section: Discussionmentioning

confidence: 99%

Coumarins of Ferulopsis hystrix: LC–MS Profiling and Gastroprotective and Antioxidant Activities of Skimmin and Peucenidin

Razuvaeva,

Toropova,

Salchak

et al. 2023

Applied Sciences

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Ferulopsis hystrix is a perennial plant of the Apiaceae family. In Buryat and Mongolian medicine, it is used as a substitute for Costus speciosus roots (ru rta), and in Tibetan medicine, it is used to cure digestive system diseases and used as a wound-healing agent. However, its metabolites and their bioactivities are still poorly understood. High-performance liquid chromatography with photodiode array detection and electrospray ionization triple quadrupole mass-spectrometric detection (HPLC–PDA–ESI–tQ–MS/MS) were used to identify approximately 42 phenolic compounds in F. hystrix, and 30 coumarins were characterized and quantified. The major compounds in F. hystrix roots were skimmin (umbelliferone 7-O-glucoside) and peucenidin (vaginidiol 3′-O-acetyl-4′-O-senecioyl ester), of which, gastroprotective and antioxidant effects were found for the first time. The abovementioned compounds exhibit a gastroprotective effect against indomethacin and steroid gastropathy by reducing the amount of damage (point, large, and strip-like erosions) in the gastric mucosa and lowering the corresponding Paul’s index. The most pronounced gastroprotective effect was exhibited by skimmin at a dose of 1 mg/kg and by peucenidin at doses of 16 and 48 mg/kg; these compounds help to limit the development of pronounced erosive–necrotic processes in the gastric mucosa. In pathological conditions, these compounds reduce malondialdehyde, increase the activity of catalase, and increase the content of reduced glutathione in the blood. Thus, this study demonstrates that F. hystrix roots are a good source of bioactive coumarins with gastroprotective potential, which supports earlier ethnopharmacological studies.

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Section: Discussionmentioning

confidence: 99%

Coumarins of Ferulopsis hystrix: LC–MS Profiling and Gastroprotective and Antioxidant Activities of Skimmin and Peucenidin

Razuvaeva,

Toropova,

Salchak

et al. 2023

Applied Sciences

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“…To study in vivo anti‐inflammatory properties, Jaya Krishna et al [ 101 ] synthesized urea derivatives of 7‐amino‐4‐methylcoumarins. The synthesized compounds 97–99 (Table 13) were tested for inhibition of edema induced by histamine, carrageenan, and formalin at a concentration of 50 mg/kg.…”

Section: Carbonic Anhydrase Inhibitors and Anticancer Activitymentioning

confidence: 99%

Pharmacological report of recently designed multifunctional coumarin and coumarin–heterocycle derivatives

Dorababu

2021

Archiv der Pharmazie

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Coumarin is a naturally available molecule and has been identified as a potent pharmacophore due to its pharmacological activity. Because of this, coumarin has been exploited synthetically to prepare a wide range of derivatives. In fact, most coumarin derivatives have been found to be less toxic, which is the most essential property for a drug molecule. Such molecules are being prepared for therapeutic use as broad‐spectrum pharmacological agents. Microbial diseases including viral diseases have become very common and are responsible for many deaths worldwide. In particular, microbial drug resistance is a problem that needs to be tackled in an effective manner. Also, for Alzheimer's disease, which affects most elderly persons, no efficient chemotherapy exists. In addition, although diabetes, a metabolic syndrome, can be treated with many drugs, there is no complete cure. Thus, more potent antidiabetic agents are required for the management of diabetes. Likewise, for the treatment of a wide range of ailments caused by microbes, genetic factors, or lifestyle‐related factors, an efficient drug regimen is needed. In view of this, coumarin derivatives are designed and evaluated. Here, coumarin derivatives that have been reported recently are compiled, classified and evaluated critically. This study briefly takes the structure–activity relationship into consideration and suggests the next suitable step. With a focus on the most potent molecules, the pharmacological activity of the evaluated molecules is described.

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Evaluation of in vitro antibacterial, DNA binding, DNA damage, DFT and antioxidant studies of aminobenzaldehyde-based heterocyclic Schiff base derivatives

Arif,

Akrema,

Pulaganti

et al. 2024

Chem. Pap.

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Heterocyclic Schiff base derivatives have been synthesized by condensation of dimethylaminobenzaldehyde and substituted amines in 1:1 molar ratio. Synthesized heterocyclic Schiff base derivatives (3a-3h) were structurally characterized by UV-visible, IR, 1 H and 13 C NMR spectroscopy, elemental analysis and mass spectrometry. Antibacterial property of heterocyclic Schiff base derivatives has been explored against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus using disc diffusion method. Results revealed that Schiff base derivatives 3c, 3f and 3h have signi cant antibacterial activity against tested bacterial strains. Heterocyclic Schiff base derivatives also explored for DNA binding interactions study with calf thymus-DNA (Ct-DNA) by absorption spectroscopy, uorescence measurements, circular dichroism, viscosity measurement and molecular docking study. Heterocyclic Schiff base derivatives 3c, 3f and 3h bind with Ct-DNA through groove binding mode with (K b ) 1.62 × 10 4 , 1.58 × 10 4 M -1 and 2.3 × 10 4 M -1 respectively. Molecular docking the target compounds was also studied against B-DNA dodecamer d(CGCGAATTCGCG) 2.Agarose gel electrophoresis study revealed that after the addition of compounds 3c, 3f and 3h, DNA damage induced by free radical has been inhibited. Antioxidant potential of heterocyclic Schiff base derivatives was also estimated by Diphenyl-1-picryl-hydrazyl (DPPH) free radical and hydrogen peroxide assay. The experimental results of the spectral properties of the synthesized derivatives 3c, 3f and 3h in solution were interpreted at the molecular level with aid of the DFT and TD-DFT/CAM-B3LYP/6-31+G(d) computational methods with Becke-3-Lee-Yang-Parr(B3LYP) exchange-correlation functional approach. Research HighlightsBioactive Schiff base were synthesized and characterized.Potent compounds showed signi cant antibacterial activity.Synthesized compounds interact with Ct-DNA through electrostatic mode of binding.Molecular docking study also con rms the binding nature of the compounds with DNA.Heterocyclic compound can also be used as signi cant antioxidant agents.DFT of the potent compounds has been also carried out for the optimization of geometry and spectroscopic data.

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Synthesis and pharmacological evaluation of schiff bases of 7-amino-4-methyl coumarins as novel anti-inflammatory agents

Cited by 5 publications

References 20 publications

Coumarins of Ferulopsis hystrix: LC–MS Profiling and Gastroprotective and Antioxidant Activities of Skimmin and Peucenidin

Coumarins of Ferulopsis hystrix: LC–MS Profiling and Gastroprotective and Antioxidant Activities of Skimmin and Peucenidin

Pharmacological report of recently designed multifunctional coumarin and coumarin–heterocycle derivatives

Evaluation of in vitro antibacterial, DNA binding, DNA damage, DFT and antioxidant studies of aminobenzaldehyde-based heterocyclic Schiff base derivatives

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