Dimedone Research Articles

Dimedone nanoparticle as a promising approach against toxoplasmosis: In vitro and in vivo evaluation

Toxoplasma gondii, an intracellular parasite, has shown drug resistance and therapeutic failure in recent years. Dimedone (DIM) has been introduced as a new chemical compound with anti-bacterial and anti-cancer properties. The aim of this study was to investigate the potential protective role of DIM nanoparticles in an animal model of toxoplasmosis. Cytotoxicity of DIM on Vero cell line assessed using MTT, and the effect of DIM on Toxoplasma gondii was evaluated by counting the number of parasites compared to the control group in vitro. The rate of pathogenesis and virulence of the parasite was checked on the liver cells of the animal model using hematoxylin-eosin staining. Furthermore, various parameters indicating oxidative stress were compared in mouse liver tissue in different groups. The release of the nanoparticle form was significantly longer than the free drugs. The IC50 of Nano-DIM was 60 µM and the reduction of intracellular parasite proliferation in the group Nano-DIM and Nano-PYR (Nano-primethamine) was significantly lower than the free drugs in vitro. Histopathology examination in the groups treated with dimedone nanomedicine showed that the degree of disintegration of the epithelium of the central vein of the liver and infiltration and vacuolization of liver cells were lower compared to the toxoplasmosis group. Additionally, the level of some oxidative stress indicators was observed to be lower in the nano-treated groups compared to other groups. The results of this study showed DIM can be used as a promising compound for anti-T. gondii activity and can prevent the proliferation of it in cells.

Efficient One-Pot Synthesis of Some New Xanthene Derivatives Based on the Reaction of Dimedone with α,α′-Bis(substituted-benzylidene) Cycloalkanones Using Catalytic Amount of pTSA

Abstract

Symmetrical molecules from reaction of beta-cyclohexanediones with acetylenedicarboxylic acid in aqueous medium

In an attempt to obtain Michael adducts in aqueous medium, 1,3-cyclohexanedione (1) or dimedone (2) and acetylenedicarboxylic acid monopotassium (3) were dissolved in water and heated to reflux. Under these conditions, two products were isolated from the reaction mixture between 1 and 3: 2-[1-(2,6-dioxocyclohexyl)ethyl]-1,3-cyclohexanedione (6) and a xanthenedione (7), which corresponds to the cyclization of 6. The reaction between 2 and 3 gave only the 2-[1-(4,4-dimethyl-2,6-dioxocyclohexyl)ethyl]-5,5-dimethyl-1,3-cyclohexanedione (8).

ChemInform Abstract: Synthesis of Some Novel Condensed Pyridine-2(1H)-thiones and Related Glycosides.

Abstract A novel synthesis of condensed pyridine-2(1 H )-thiones and 3-deazapyrimidine glycosides is described utilizing arylmethylenecyanothioacetamides and dimedone as starting components.

Double Spiro‐bis‐heterocyclization of 5‐Methoxycarbonyl‐2,3‐dihydro‐2,3‐pyrroledione by Treatment with N‐Aryl‐Substituted Dimedone Imine.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Double spiro-bis-heterocyclization of 5-methoxycarbonyl-2,3-dihydro-2,3-pyrroledione by treatment with N-aryl-substituted dimedone imine

Double spiro-bis-heterocyclization of 5-methoxycarbonyl-2,3-dihydro-2,3-pyrroledione by treatment with N-aryl-substituted dimedone imine

Reactions of Phenols with Lewis Acids: XIX. Complexes of ortho-Quinones and Benzenediols with Aluminum Bromide

Enthalpies of the reactions of Al2Br6 with 3,5-di-tert-butyl-1,2-benzoquinone, 1,2-naphthoquinone, 9,10-phenanthrenequinone, dimedone, isomeric benzenediols, and 4-methoxyphenol have been determined.

Chlorosphaeropsidone and Epichlorospaeropsidone, Two New Chlorinated Dimedone Methyl Ethers Isolated from Liquid Cultures of "Sphaeropsis sapinea" f. sp. "cupressi"

Two new dimedone methyl ethers, named chlorosphaeropsidone and epichlorosphaeropsidone were isolated from the culture filtrates of Sphaeropsis sapinea f. sp. cupressi, the causal agent of a canker of Italian cypress (Cupressus sempervirens L.). The same fungus also produced various phytotoxic metabolites: three pimarane diterpenes (sphaeropsidins A, B and C) and two dimedone methyl ethers (sphaeropsidone and episphaeropsidone). Chlorosphaeropsidone and epichlorosphaeropsidone were characterized using chemical and spectroscopic methods as two 6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-ones epimers at C-6. Their relative and absolute configurations were established by NMR, X-ray analysis and circular dichroism. Assayed on host plants they did not show phytotoxic activity. Comparison with other sphaeropsidones suggested that this might result from opening of the epoxy ring.

Kinetics and Mechanism of the Oxidation of Dimedone by Alkaline Permanganate

The kinetics of oxidation of dimedone (DM) by permanganate in low and high alkali concentrations at a constant ionic strength has been studied spectrophotometrically. The reaction seems to proceed by two different mechanisms. At higher concentrations of alkali the reaction exhibits first, less than unity and zero order dependence of the rate on [permanganate ion], [DM] and [alkali], respectively, while at lower concentrations of alkali, all the orders are the same except for [OH−] the order of [OH″] is less than unity. In both the cases of [OH−], the. initial addition of products does not affect the rate significantly, while an increase in ionic strength and decrease in dielectric constant enhance the rate of the reaction. Plausible mechanisms consistent with the kinetic data were proposed and constants involved in the mechanisms have been evaluated. There is good agreement between observed and calculated rate constants at varying conditions of the experiments. The activation parameters with respect to the slow step of the mechanism have been computed.

ChemInform Abstract: Reaction of β‐Chloroacroleins with Dimedone.

ChemInform Abstract: Reaction of β‐Chloroacroleins with Dimedone.

ChemInform Abstract: Reaction of 4‐Nitrophthalodinitrile with Dimedone.

AbstractThe reaction between 4‐nitrophthalodinitrile (I) and C nucleophiles such as dimedone (II) has not been investigated up to now.

ChemInform Abstract: Reaction of Dimedone Enaminone with β‐Nitrostyrene.

AbstractApossible mechanism for the formation of the dihydrobenzoxazinone (VII) from dimedone (I) and β‐nitrostyrene (III) is proposed: initially, deprotonation after the alkylation of the enaminone (II) with (III) gives (IV) (in a kinetically controlled reaction).

The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with β-Diketones

Dimedone (1) and p-methoxyphenyllead triacetate (2) react in chloroform containing pyridine at 40� to give 2,2-bis(p-methoxyphenyl)-5,5-dimethylcyclohexane-,3-dione (3) in high yield. This arylationreaction of β-diketones has been examined with 2-methylcyclohexane-1,3-dione, 2-methylcyclopentane-1,3-dione, acetylacetone and 2-acetyl-3,4-dihydronaphthalen-l(2H)-one, and in all cases synthetically useful yields of arylated products were obtained. The vinylogous β-diketone, 6β-acetylcholest-4-en-3-one, also underwent the reaction to give a mixture of 6β-acetyl-6α-(p-methoxypheny1)-cholest-4-en-3-one (21) and the corresponding 6β-aryl compound (22).

The reactions with aldehydes of enaminones derived from dimedone

The primary and a secondary enaminone derived from dimedone react with formaldehyde to give the expected methylenebisenaminone derivatives (V). Depending upon the conditions, further reactions can take place to give 3,4,5,6,9,10-hexahydro-3,3,6,6-tetramethylacridine-1(2H),8(7H)-diones (VI) or 1,2,3,4,7,8-hexahydro-4′,4′,7,7-tetramethylquinoline-3-spirocyclohexane-2′,5(6H),6′-triones (VII). The corresponding reaction with benzaldehyde gives only the decahydroacridinedione (VId); that with acetaldehyde gives either the decahydro-acridinedione (VIc) or 1,2,7,8-tetrahydro-2,4,7,7-tetramethyl-4H-3,1-benzoxazin-5(6H)-one (XI).

Alkylation of Dimedone with 1,4-Dibromobutyne-2 and trans-1,4-Dibromobutene-2.

Alkylation of Dimedone with 1,4-Dibromobutyne-2 and trans-1,4-Dibromobutene-2.

Base catalyzed condensation of dimedone with β-nitrostyrene

Base catalyzed condensation of dimedone with β-nitrostyrene