Design, synthesis, molecular docking and biological evaluation of imides, pyridazines, and imidazoles derived from itaconic anhydride for potential antioxidant and antimicrobial activities

Nayak, Prakash S.; Narayana, B.; Sarojini, B. K.; Sheik, Sana; Shashidhara, K. S.; Chandrashekar, K. R.

doi:10.1016/j.jtusci.2014.09.005

Cited by 20 publications

(8 citation statements)

References 21 publications

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“…At 100 μg/ml, the absorbance value of Cu‐4AP‐Br is above 1.0. This result was similar to a previous study reporting that synthesized compounds (Itaconic anhydride (ITA)) exhibited high reducing power potential . It has been reported that the reducing properties are generally associated with the presence of reductones, shown to exert antioxidant action by donating a hydrogen atom and breaking the free radical chain …”

Section: Resultssupporting

confidence: 91%

Catalytic and biological valorization of a supramolecular mononuclear copper complex based 4‐aminopyridine

Hfidhi

Bkhairia

Atoui

et al. 2019

Applied Organom Chemis

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Hydrothermal reaction of copper bromide with 4‐aminopyridine in DMF solution yields a new mononuclear copper complex [Cu(C5H6N2)4]2Br.2(C3H7NO) abbreviated Cu‐4AP‐Br. The product was characterized, structurally, by single‐crystal X‐ray diffraction analysis and, thermally, by DSC‐ATG measurement. The inorganic–organic hybrid compound Cu‐4AP‐Br crystallizes in the centrosymmetric space group Pbcn, exhibiting a supramolecular network. Simultaneous DSC‐ATG analysis shows that this compound remains stable up to 100 °C and then performs a successive decompositions accompanied with endothermic peaks. The complex Cu‐4AP‐Br was applied as a catalyst in the Heck coupling reaction under ultrasonic irradiation in various reaction conditions. The yields, obtained for a short period of time, allow us to consider this complex, generating selectivity on the external position of styrene with a preference of the trans form over cis, as an excellent catalyst for this type of reaction. Interestingly, Cu‐4AP‐Br displayed important antibacterial (Gram‐positive and Gram‐negative) and antioxidant activities (β‐carotene bleaching inhibition, scavenging effect on DPPH free radical, and reducing power).

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Section: Resultssupporting

confidence: 91%

Catalytic and biological valorization of a supramolecular mononuclear copper complex based 4‐aminopyridine

Hfidhi

Bkhairia

Atoui

et al. 2019

Applied Organom Chemis

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“…The essential oil and solvent extracts of A. graveolens were reported to exhibit cardioprotective [ 7 ], hepatoprotective [ 16 ], and nephroprotective properties [ 17 ]. In general, the chemical composition of volatile oils varies significantly, depending on a variety of factors, including geographical, soil, and climate conditions, and there have been various studies that have demonstrated the variation in essential oils in Apiaceae species in recent years [ 18 , 19 ]. Swollen joints, redness, joint pain or stiffness, and loss of joint functions are the major symptoms of inflammation, and it is closely associated with an increased production of ROS (reactive oxygen species) and RNOS (reactive nitrogen oxide species) [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Determination of Chemical Composition, In Vitro and In Silico Evaluation of Essential Oil from Leaves of Apium graveolens Grown in Saudi Arabia

et al. 2021

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The aim of this study was to explore the composition and evaluate the in silico and in vitro antioxidants and antimicrobial and anti-inflammatory effects of Apium graveolens var. dulce leaves essential oil (AGO) collected from Al-Kharj (Saudi Arabia). AGO was isolated using the hydro-distillation method, and its composition was studied using gas-chromatography-mass Spectrometry (GC–MS), antimicrobial activities using well diffusion assay, and antioxidant and anti-inflammatory activities using spectrophotometric methods. The pharmacological activities of their major compounds were predicted using PASS (prediction of activity spectra for substances) and drug-likening properties by ADME (absorption, distribution, metabolism, and excretion) through web-based online tools. Isocnidilide (40.1%) was identified as the major constituent of AGO along with β-Selinene, Senkyunolide A, Phytyl acetate, and 3-Butylphthalide. AGO exhibited a superior antibacterial activity, and the strongest activity was detected against Gram-positive bacteria and Candida albicans. Additionally, it exhibited a weaker antioxidant potential and stronger anti-inflammatory effects. PASS prediction supported the pharmacological finding, whereas ADMET revealed the safety of AGO. The molecular docking of isocnidilide was carried out for antibacterial (DNA gyrase), antioxidant (tyrosinase), and anti-inflammatory (cyclooxygenase-2) activities. The docking simulation results were involved hydrophilic interactions and demonstrated high binding affinity of isocnidilide for anti-inflammatory protein (cycloxygenase-2). The presence of isocnidilide makes AGO a potential anti-inflammatory and antimicrobial agent. AGO, and its major metabolite isocnidilide, may be a suitable candidate for the future drug development.

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“…The synthesis of compounds 5 a,b was performed by the intramolecular cyclisation of compounds 3 a,b in basic media with conventional and also MW mediated methods with the aim to introduce the 1,2,4‐triazole nucleus into piperazine skeleton, because it is well known that more efficacious bioactive compounds can be designed by joining two or more biologically active heterocyclic systems together in a single molecular framework . In addition, type of compounds 5 a,b can be considered as useful tolls having active SH group for further one pot three component aminoalkylation reactions leading to the formation new bioactive compounds.…”

Section: Resultsmentioning

confidence: 99%

Design, Microwave‐Assisted and Conventional Synthesis of New Hybrid Compounds Derived From 1‐(4‐Fluorophenyl)piperazine and Screening for Their Biological Activities

et al. 2018

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The synthesis of new conazole analogues (8 a-d) was performed by three steps sequential reactions of compounds 5 a,b containing the condensation with 4-chlorophenylethanone, reduction of carbonyl function and O-alkylation intermediates 2-The treatment of triazoles 4-Benzyl-5-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-2,4-dihydro-4H-1,2,4-triazole-3-thiol (5 a) and 5-{[4-(4-Fluorophenyl)pi-perazin-1-yl]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol (5 b) with several amines in the presence of formaldehyde generated the corresponding Mannich bases (9-12). All the reactions were examined under traditional and microwave irradiation conditions, and optimum conditions were defined. The antimicrobial, antiurease and antioxidant activities of the newly synthesized compounds were screened. Most of them had potent activity against to test microorganism. Especially mannich bases showed minimum inhibitory concentration (MIC) values between 0.24 and 1.9 mg/mL.[a] Dr.

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Design, synthesis, molecular docking and biological evaluation of imides, pyridazines, and imidazoles derived from itaconic anhydride for potential antioxidant and antimicrobial activities

Cited by 20 publications

References 21 publications

Catalytic and biological valorization of a supramolecular mononuclear copper complex based 4‐aminopyridine

Catalytic and biological valorization of a supramolecular mononuclear copper complex based 4‐aminopyridine

Determination of Chemical Composition, In Vitro and In Silico Evaluation of Essential Oil from Leaves of Apium graveolens Grown in Saudi Arabia

Design, Microwave‐Assisted and Conventional Synthesis of New Hybrid Compounds Derived From 1‐(4‐Fluorophenyl)piperazine and Screening for Their Biological Activities

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