Anti-Infective Quinone Derivatives of Recent Patents

Koyama, Junko

doi:10.2174/157489106775244073

Cited by 82 publications

(38 citation statements)

References 49 publications

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“…Overall yields for this process are moderate. 125 Cimen et al 127 have recently reported TMP to TMQ oxidation with potassium peroxomonosulfate, KHSO 5 , present in oxone catalysed by either iron phthalocyanin tetrasulfonate, [FePcTS] The highlight of the above strategy is that the reaction proceeded with 100% yield when the oxidant:substrate:catalyst molar ratios were 1200:300:1. Phenols with bulky substituents can also be converted to corresponding benzoquinones.…”

Section: Synthesis Of 14-benzoquinones From Phenolsmentioning

confidence: 99%

“…3 Their role as electron transfer agents in primary metabolic processes like photosynthesis and respiration is vital to human life. A large number of chemical derivatives with 1,4-benzoquinone as the basic subunit exhibit prominent pharmacological applications such as antibiotic, 4,5 antitumor, [6][7][8][9] antimalarial, 7,10 antineoplastic, 11 anticoagulant 12 and herbicidal activity. 13 Wide applications of quinones can also be found in the field of synthetic organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…The compound 4 is an important quinone called primin. 34 It is noteworthy to mention the insect antifeedent, 34 antimicrobial and antineoplastic activities 35,36 of primin and its quinol analogue miconidin (5). Another important quinone, 2-methoxy-6-benzyl-1,4-benzoquinone (6) was also synthesized and tested in the same strain.…”

Section: Introductionmentioning

confidence: 99%

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Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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Section: Synthesis Of 14-benzoquinones From Phenolsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

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“…For instance, oxidative stress may be involved as one interpretation of the morphological changes, based on the fact that many quinones generate reactive oxygen species such as oxidative radicals, hydrogen peroxide, and superoxides by redox cycling involving quinones, NADH, and oxygen under aerobic conditions in the cells. 33) In summary, we isolated SPF, which is cytotoxic to rat liver cancer cells, from yellow hornet nests. To our knowledge, this is the first example of the isolation and structural determination of an anticancer quinone molecule from the nest of a social wasp.…”

Section: Discussionmentioning

confidence: 92%

A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

Fujiwara

Mangetsu

Yang

et al. 2008

Biological & Pharmaceutical Bulletin

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A biologically active quinone that exhibits a growth-inhibitory effect on rat liver cancer cells was isolated from the nest of a social wasp, Vespa simillima (Vespinae, Vespidae). The structure was unambiguously determined by NMR and synthetic experiments and identified as being 7,8-seco-para-ferruginone. The synthetic quinone showed potent growth-inhibitory effects on rat hepatoma cells (IC 50 value‫9.1؍‬ m mM). Morphological analyses of dRLh84 cells using the synthetic compound were tested. Chromatin coagulation was induced by the synthetic compound at 31.6 m mM.

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“…It has been reported that malaria parasite degrades up to 80 % of the haemoglobin in the host cell and releases heme which is toxic to parasite and their host. 17 Neutralization of heme occurs mainly due to hemozoin formation by the parasites. Inhibition of hemozoin formation is, therefore, an important drug target to kill the parasite cell.…”

Section: Antimalarial Activitymentioning

confidence: 99%

In vivo Antimalarial Evaluation of Embelin and its Semi-Synthetic Aromatic Amine Derivatives

Bezu¹,

Bisrat²,

Asres³

2015

Phcog J

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Background: In less developed countries like Ethiopia, malaria is traditionally treated by remedies prepared from medicinal plants. One such plant that falls in this category is Embelia schimperi Vatke whose fruits are employed for the treatment of a variety of ailments including taeniasis and malaria. Objective: In the present study, the in vivo antimalarial activity of embelin isolated from the fruits of Embelia schimperi Vatke and its semisynthetic aromatic amine derivatives was evaluated. Methods: Silica gel column chromatography was used to isolate embelin from the ethyl acetate extract of the fruits of E. schimperi. Aromatic substituted embelin derivatives were semi-synthesized by using a one-step condensation reaction of embelin with aromatic amines. The compounds were characterized based on their UV, IR, HR-ESIMS, 1 H and 13 C NMR and DEPT-135 spectral data. Antimalarial activity was evaluated using a modified Peter's 4-day suppressive test against chloroquine sensitive Plasmodium berghei infection in mice. Results: Embelin and the semi-synthetic derivatives showed significant (p<0.05) in vivo antimalarial activity in a dose-dependent manner with 47.8-74.7% parasite suppression at tested doses of 100-400 mg/kg. Among the compounds semi-synthesized, 5-(p-tolylamino)-2-hydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione showed maximum antimalarial activity (74.7 % suppression) at a dose of 400 mg/kg. No major signs of toxicity were observed when either embelin or the semi-synthesized derivatives were administrated to mice at the highest tested dose (2 g/kg). Conclusion: The results underline that the antimalarial activity of embelin can be improved by preparing its aromatic semi-synthetic amine derivatives without affecting the safety of the parent molecule.Keywords: Antimalarial, Aromatic substituted embelin, A 4-Day suppressive test, Embelia schimperi, Embelin. SUMMARY• Embelin is the major constituent of the fruits of Embelia schimperi Vatke.with an established antimalarial activity.• It has a long alkyl chain (undecyl) as a substituent, which confers solubility in the non-polar phase and cell permeability.• Aromatic amine derivatives of embelin were semi-synthesized and one of the compounds obtained by condensation of embelin with p-toludine showed improved antimalarial activity.

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Anti-Infective Quinone Derivatives of Recent Patents

Cited by 82 publications

References 49 publications

Recent advances in 1,4-benzoquinone chemistry

Recent advances in 1,4-benzoquinone chemistry

A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

In vivo Antimalarial Evaluation of Embelin and its Semi-Synthetic Aromatic Amine Derivatives

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