Synthesis, molecular properties prediction and anticancer, antioxidant evaluation of new edaravone derivatives

Polkam, Naveen; Ramaswamy, V; Rayam, Parsharamulu; Allaka, Tejeswara Rao; Anantaraju, Hasitha Shilpa; Sriram, Dharmarajan; Yogeeswari, Perumal; Gandamalla, Durgaiah; Yellu, Narsimha Reddy; Sridhar, Balasubramanian; Anireddy, Jaya Shree

doi:10.1016/j.bmcl.2016.03.024

Cited by 36 publications

(15 citation statements)

References 39 publications

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“…Physicochemical properties of the compounds were also estimated, such as cLogP, the logarithm of its partition coefficient between n -octanol and water, which is a property that describes the molecular hydrophobicity. The value range for this property varied from 2.83 to 4.6 in the studied compounds, with 3 and 4 presenting the lower values [ 30 , 31 ]. As the target molecules’ values are less than 5 , it indicates a reasonable probability they will be well absorbed [ 29 , 32 ].…”

Section: Resultsmentioning

confidence: 99%

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In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

et al. 2017

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Several indolylquinone analogues of perezone, a natural sesquiterpene quinone, were characterized in this work by theoretical methods. In addition, some physicochemical, toxicological and metabolic properties were predicted using bioinformatics software. The predicted physicochemical properties are in agreement with the solubility and cLogP values, the penetration across the cell membrane, and absorption values, as well as with a possible apoptosis-activated mechanism of cytotoxic action. The toxicological predictions suggest no mutagenic, tumorigenic or reproductive effects of the four target molecules. Complementarily, the results of a performed docking study show high scoring values and hydrogen bonding values in agreement with the cytotoxicity IC50 value ranking, i.e., indolylmenadione > indolylperezone > indolylplumbagine > indolylisoperezone. Consequently, it is possible to suggest an appropriate apoptotic pathway for each compound. Finally, potential metabolic pathways of the molecules were proposed.

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Section: Resultsmentioning

confidence: 99%

“…Drug solubility (expressed as Log S) is an important factor to describe the absorption process. Poor solubility leads to poor absorption and bioavailability [ 30 , 31 , 32 , 33 ]. The common commercial drugs have values of Log S greater than −4.…”

Section: Resultsmentioning

confidence: 99%

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

et al. 2017

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“…In this connection molecules with score > 0.00 indicates more active, between À 0.50 and 0.00 moderately active and < À 0.50 inactive. [24] All the compounds exhibit value between 0.01 and 0.43 indicating that they have high proba-bility to be active. Also all the compounds showed positive values ranging from 0.02 to 0.38 in column 4, indicating good bioactivity specifically in Kinase inhibition.…”

Section: Computation Studymentioning

confidence: 99%

Synthesis, Molecular Properties Prediction and Antimicrobial Activity of Imidazolyl Schiff Bases, Triazoles and Azetidinones

Rekha

Ummadi

Padmaja

et al. 2019

Chemistry & Biodiversity

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Benzylidenehydrazinyl imidazoles (3) are prepared from 2‐hydrazinyl imidazoles (2) on treatment with hydrazine. The imine functionality in 3 is utilized to develop 5′‐aryl‐N‐(4‐aryl‐1H‐imidazol‐2‐yl)‐1H‐1,2,3‐triazol‐1‐amines (5) by 1,3‐dipolar cycloaddition of diazomethane followed by aromatization with I2 in DMSO. Compounds 3 are also explored to prepare 4′‐aryl‐1‐(4‐aryl‐1H‐imidazol‐2‐ylamino)‐3‐chloroazetidin‐2‐ones (6) on treatment with chloroacetyl chloride. The Molinspiration calculations predicted that 3, 5 and 6 have molecular hydrophobicity, conformational flexibility, good intestinal absorption and bioactivity scores. The chloro, bromo and nitro substituted imidazolyl azetidinones (6c, 6d, 6f) and nitro substituted imidazolyl triazole (5f) exhibited excellent antibacterial activity on B. subtilis, whereas chloro and nitro substituted imidazolyl triazoles (5c, 5f) showed prominent antifungal activity on A. niger.

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“…Several reasons contribute to the attrition of drug candidates, including pharmacokinetic difficulties, insufficient efficacy, and adverse reactions in animal and humans. In the development phase of oral drugs, nearly 30% of drug candidates fail due to poor ADME properties [ 40 ]. Bioactive cinnamylideneacetophenones were also subjected to pharmacokinetic filters.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones

et al. 2017

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Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 µM against Staphylococcus aureus, Streptococcus mutans, and Streptococcus sanguinis. Compounds 2, 7, 10, and 18 presented potent effects against Mycobacterium tuberculosis (57.2 µM ≤ MIC ≤ 70.9 µM). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log Po/w were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of 3 and 4 were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 µM ≤ IC50 ≤ 96.7 µM) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski’s and Veber’s rules, corroborating their potential bioavailability by an oral route.

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Synthesis, molecular properties prediction and anticancer, antioxidant evaluation of new edaravone derivatives

Cited by 36 publications

References 39 publications

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

Synthesis, Molecular Properties Prediction and Antimicrobial Activity of Imidazolyl Schiff Bases, Triazoles and Azetidinones

Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones

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