Synthesis, crystal structure investigation, DFT studies and DPPH radical scavenging activity of 1-(furan-2-ylmethyl)-2,4,5-triphenyl- 1H -imidazole derivatives

Rajaraman, D.; Sundararajan, G.; Rajkumar, R.; Bharanidharan, S.; Krishnasamy, K.

doi:10.1016/j.molstruc.2015.11.084

Cited by 32 publications

(6 citation statements)

References 38 publications

(33 reference statements)

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“…Interestingly, five unique structures [AFUVUU (Mohamed et al, 2013b), IFUMON (Mohamed et al, 2013c), OZEGEG (Kapoor et al, 2011), YOCTAM (Ghoranneviss et al, 2008) and SUYZIX (Rajaraman et al, 2016)] are found of related compounds with 4-chlorophenyl groups on C2 and but none of these have alcohol substituents on N1.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of 1-[2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

et al. 2017

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Section: Database Surveymentioning

confidence: 99%

Crystal structure of 1-[2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

et al. 2017

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“…Literature reports indicated a correlation between a higher HOMO-LUMO gap of the electronic systems and a lower reactivity of the respective compounds [7,34,35]. Thus, a compound with a low HOMO-LUMO gap could be a good antioxidant.…”

Section: Resultsmentioning

confidence: 99%

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

et al. 2019

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Oxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which oxidative stress is suggested as the root cause. The thiazolidine-2,4-dione derivatives have been reported to possess various pharmacological activities and the phenol moiety is known as a pharmacophore in many naturally occurring and synthetic antioxidants. Twelve new phenolic derivatives of thiazolidine-2,4-dione were synthesized and physicochemically characterized. The antioxidant capacity of the synthesized compounds was assessed through several in vitro antiradical, electron transfer, and Fe2+ chelation assays. The top polyphenolic compounds 5f and 5l acted as potent antiradical and electron donors, with activity comparable to the reference antioxidants used. The ferrous ion chelation capacity of the newly synthesized compounds was modest. Several quantum descriptors were calculated in order to evaluate their influence on the antioxidant and antiradical properties of the compounds and the chemoselectivity of the radical generation reactions has been evaluated. The correlation with the energetic level of the frontier orbitals partially explained the antioxidant activity, whereas a better correlation was found while evaluating the O–H bond dissociation energy of the phenolic groups.

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“…A free radical scavenging activity test using DPPH radical was conducted in accordance with Rajaraman et al () with some modifications. In brief, Trolox solution in water was prepared at different concentrations (0.015–10 μg/ml) and used as the standard.…”

Section: Methodsmentioning

confidence: 99%

Statistical optimization for precipitation of bioactive compounds from extracted Centella asiatica using gas anti‐solvent technique

Charoenchaitrakool

Niamnuy

Dittanet

et al. 2019

J Food Process Engineering

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Centella asiatica is a well-known herbal medicine used for antioxidant and antibacterial purposes. Main compounds in the group of triterpene saponins, namely, asiaticoside, asiatic acid, madecassoside, and madecassic acid are considered as the active compounds. These active ingredients were extracted from C. asiatica dried powder by the maceration method. The extracted solution was then used as a starting solution for the gas anti-solvent (GAS) precipitation. The effects of % ethanol in a mixed solvent of ethanol and methanol (0-100%), carbon dioxide flow rate (3-9 ml/min), and temperature (25-45 C) on the amount of precipitates were investigated using a Box-Behnken design of experiments. It was found that % ethanol in the mixed solvent was significant at 5% significance level on madecassoside, asiaticoside, and total triterpene saponins. Higher amounts of total triterpene saponins could be precipitated when using low % ethanol and low temperature. At the optimal conditions, the amount of madecassoside, asiaticoside, madecassic acid, and asiatic acid were found to be 5,733 ± 537, 2,948 ± 249, 1,678 ± 163, and 436 ± 17 μg/5 ml of extracted solution, respectively. In the antioxidant studies, the highest Trolox equivalent found in the GAS products using 2,2-diphenyl-1-picrylhydrazyl and 2,2-azion-bis-3-ethylbenzothiazo line-6-sulphonic acid assays was 5,622 ± 336 and 10,729 ± 820 μg/5 ml of extracted solution. Practical applicationsThe novelty of this work covers the feasibility of applying gas anti-solvent (GAS) technique for precipitation of bioactive compounds from extracted Centella asiatica and a statistical optimization of the operating parameters on the highest amount of precipitates. This work is important for extraction and purification applications focused on obtaining high purity of bioactive compounds from crude extracts. The use of dense CO 2 as an anti-solvent not only requires mild operating conditions but also provides a solvent-free product. Therefore, the application of the GAS process can then be extended to precipitate active ingredients from other herbal extracts.

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Synthesis, crystal structure investigation, DFT studies and DPPH radical scavenging activity of 1-(furan-2-ylmethyl)-2,4,5-triphenyl- 1H -imidazole derivatives

Cited by 32 publications

References 38 publications

Crystal structure of 1-[2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

Crystal structure of 1-[2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies

Statistical optimization for precipitation of bioactive compounds from extracted Centella asiatica using gas anti‐solvent technique

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