Green synthesis of 1,4-quinone derivatives and evaluation of their fluorescent and electrochemical properties

Ravichandiran, Palanisamy; Kannan, R.; Ramasubbu, A.; Muthusubramanian, Shanmugam; Samuel, Vasanth Kumar

doi:10.1016/j.jscs.2012.09.011

Cited by 18 publications

(13 citation statements)

References 17 publications

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“…A new series of 1,4‐naphthoquinone‐based compounds were synthesized, and the synthetic routes for preparation of compounds 3–5 w and 5 x–5 aa are presented in Schemes and . The parent molecule 3 was synthesized via the nucleophilic substitution reaction between 2,3‐dichloro‐1,4‐naphthoquinone 1 and 4‐aminophenyl sulfone 2 using our previously reported method . Compound 4 was prepared by nucleophilic substitution of an equal molar concentration of compound 3 and cyclohexanethiol in dry acetone.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Ravichandiran

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et al. 2019

ChemistryOpen

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1,4‐Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4‐naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity. In this present investigation, two Gram‐positive and five Gram‐negative bacterial strains and one pathogenic yeast strain were used to determine the antibacterial activity. Naphthoquinones tested for its antibacterial potencies, among seven of them displayed better antimicrobial activity against Staphylococcus aureus ( S. aureus ; 30–70 μg/mL). Some of the tested compounds showed moderate to low antimicrobial activity against Pseudomonas aeruginosa ( P. aeruginosa ) and Salmonella bongori ( S. bongori ; 70–150 μg/mL). In addition, most active compounds against S. aureus were evaluated for toxicity to human blood cells using a hemolysis assay. For better understanding, reactive oxygen species (ROS) generation, time‐kill kinetic study, and apoptosis, necrosis responses were investigated for three representative compounds.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Ravichandiran

Masłyk

Sheet³

et al. 2019

ChemistryOpen

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“…Am ixture of 2,3-dichloro-1,4-naphthoquinone and 4-aminophenyl sulfonamide hydrochloride salt in ethanol, in the presence of N,N-diethylaniline as ac atalyst, was held at reflux for 18 h; the product yield was approximately 72 %. In our previous report, [21] we synthesized compound 3 by as imple method:t he reaction between 2,3-dichloro-1,4naphthoquinone 1 and 4-aminophenyl sulfone 2 in water was performed at reflux for 2h to generate an 88 %p roduct yield (compound 3)w ith high purity.N otably,w hen the reaction was performed for 96 h, it generated a9 5-96 %p roduct yield. Compared with previously published methods, our present methodology shows the benefits of good yield with shorter reaction time and green synthetic conditions.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

et al. 2019

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1,4‐Naphthoquinones are exceptional building blocks in organic synthesis and have been used to synthesize several well‐known pharmaceutically active agents. Herein we report the synthesis, structural characterization, and biological evaluation of new phenylaminosulfanyl‐1,4‐naphthoquinone derivatives. We evaluated the cytotoxic activity of the synthesized compounds against three human cancer cell lines: A549, HeLa, and MCF‐7. Most of the synthesized compounds displayed potent cytotoxic activity. Specifically, compounds 5 e [3,5‐dichloro‐N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)benzamide], 5 f [N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)‐3,5‐dinitrobenzamide], and 5 p [N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)thiophene‐2‐carboxamide] showed remarkable cytotoxic activity. The synthesized compounds showed low toxicity in normal human kidney HEK293 cells. The cytotoxic mechanism of compounds 5 e, 5 f, and 5 p was explored in MCF‐7 cells. The results confirmed that these three compounds induce apoptosis and arrest the cell cycle at the G1 phase. In addition, compounds 5 e, 5 f, and 5 p were found to induce apoptosis via upregulation of caspase‐3 and caspase‐7 proteins as well as by upregulation of the gene expression levels of caspases‐3 and ‐7. Our findings demonstrate that compounds 5 e, 5 f, and 5 p could be potent agents against a number of cancer types.

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“…Recent studies from our research group (Bayrak et al, , ; Yildirim et al, ) and that of Ferreira (Dias et al ), Ryu (Ryu, Song, Lee, Hong, Yoon, & Kim, ; Ryu, Yoon, Song, Im, Kim, & Kim, ), Tandon (Tandon, Maurya, Kumar, Rashid, & Panda, ; Tandon et al, ), and Valderrama (Valderrama, Ibacache, Rodriguez, Theoduloz, & Benites, ; Valderrama, Leiva, Rodriguez, Theoduloz, & Schmeda‐Hirshmann, ) have shown that electrophilic character of 1,4‐quinones can undergo with neutral and/or anionic nucleophiles in different conditions in versatile reactions, thus leading to various biologically active (hetero)cyclic quinone structures for their pharmacological properties. In this regard, as a result of the immense value of quinone compounds in organic and medicinal chemistry, 1,4‐quinones have been studied for over a half‐century as an important class of building blocks and still continue to attract considerable attention due to the broad range of synthetic and medicinal applications (Bayrak et al, ; Johnson‐Ajinwo et al, ; Pingaew et al, ; Ravichandiran, Kannan, Ramasubbu, Muthusubramanian, & Samuel, ; Ravichandiran, Subramaniyan, et al, ; Tandon & Kumar, ; Valderrama et al, ; Wellington, ).…”

Section: Introductionmentioning

confidence: 99%

A novel series of chlorinated plastoquinone analogs: Design, synthesis, and evaluation of anticancer activity

et al. 2020

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Herein, we report the synthesis and cytotoxic effects of novel chlorinated plastoquinone analogs (ABQ1–17) against different leukemic cells. Compounds ABQ3, ABQ11, and ABQ12 demonstrated a pronounced antiproliferative effect against chronic myelogenous leukemia (CML) K562 cell line with IC50 values of 0.82 ± 0.07, 0.28 ± 0.03, and 0.98 ± 0.22 μM, respectively. Among them, ABQ11 showed approximately three times higher selectivity than imatinib on CML. ABQ11‐treated CML cells induced significant apoptosis at low concentration. Inhibitory effect of ABQ11 against eight different tyrosine kinases, including ABL1, was investigated. ABQ11 inhibited ABL1 with IC50 value of 13.12 ± 1.71 μM, indicating that the moderate inhibition of ABL1 kinase is just an in‐part mechanism of its outstanding cellular activity. Molecular docking of ABQ11 into ABL1 kinase ATP‐binding pocket revealed the formation of some key interactions. Furthermore, DNA cleavage assay showed that ABQ11 strongly disintegrated DNA at 1 μM concentration in the presence of iron (II) complex system, assuming that the major mechanism for the anticancer effects of ABQ11 is DNA cleavage. In silico ADMET prediction revealed that ABQ11 is a drug‐like small molecule with a favorable safety profile. Taken together, ABQ11 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from imatinib.

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Green synthesis of 1,4-quinone derivatives and evaluation of their fluorescent and electrochemical properties

Cited by 18 publications

References 17 publications

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

A novel series of chlorinated plastoquinone analogs: Design, synthesis, and evaluation of anticancer activity

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