• Bulletin of the Korean Chemical Society
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• v.20 no.1
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• pp.76-80
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• 1999

The effects of zeolites on the intramolecular [2+2] photocycloadditions of 3-(3-butenyl)cyclohex-2-enone (la) and 3-(2-propenoxy)cyclohex-2-enone (lb) were investigated. When la adsorbed in cation-exchanged zeolites X and Y was irradiated through a Pyrex filter, the products from the 1,6-ring closure biradical increased compared to the results from the photoreaction in homogeneous solutions. In the intramolecular 1,5-ring closure photocycloaddition of la and lb, the products from the cis-fused intermediates increased in zeolites X and Y. The regiochemical and stereochemical outcomes of the photocycloadditions in the zeolites were interpreted by the binding of the guest molecules with the cations in the supercages.

• YAKHAK HOEJI
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• v.45 no.1
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• pp.16-22
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• 2001

Novel yakuchinone derivatives have been designed, synthesized and evaluated their inhibitory activity of NO production in lipopolysaccharide (LPS)-activated macrophages. From this study, some enone compounds have been found to be highly active in the assay. In view of the importance of NO in septic shock and inflammation, these compounds may be useful candidates for the development of new drug to treat endotoxemia and inflammation accompanying overproduction of NO.

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.141-147
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• 1993

A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.

• Bulletin of the Korean Chemical Society
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• v.33 no.2
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• pp.443-448
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• 2012

Ferrocenyl chalcones (Fc-C(O)CH=CH-Ar: Fc-Ar) with mono- and di-1-naphthalenyl moieties (Fc-1Naph and Fc-d1Naph) were prepared and spectroscopically characterized. The enone bridge was in the s-cis conformation and the $\pi$-electrons on the C=C bond were further delocalized on the bridge. The naphthalenyl moiety deviates greatly from the enone-Cp plane by $26.9(1)^{\circ}$. Cyclic voltammetry measurements for Fc-1Naph exhibit one reversible cycle for the redox of the ferrocenyl moiety at a lower potential, and one irreversible oxidation peak at the higher potential region. For Fc-d1Naph, the cyclic voltammogram is more featureless. Fluorescence properties for both compounds are active in polar solvents with $\lambda_{em}$ = 500 nm (EtOH) and $\lambda_{em}$ = 512 nm (MeOH) for Fc-1Naph and $\lambda_{em}$ = 496 nm (EtOH) and $\lambda_{em}$ = 508 nm (MeOH) for Fc-d1Naph. The intensity of Fc-d1Naph is more than twice than that of Fc-1Naph. The fluorescence properties for both compounds are inactive in the less polar solvents such as $CH_3CN$, $CH_2Cl_2$ and $CHCl_3$.

• Bulletin of the Korean Chemical Society
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• v.33 no.2
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• pp.620-624
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• 2012

An efficient synthesis of poly-substituted furans, pyrroles, and thiophenes was carried out in a regiocontrolled manner via a three-step process; (i) conjugate addition of methyl cyanoacetate derivatives to ${\alpha}$,${\beta}$-enones, (ii) CuI-mediated aerobic oxidation, and (iii) Paal-Knorr type synthesis of five-membered heterocycles.

• Natural Product Sciences
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• v.1 no.1
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• pp.1-4
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• 1995

MeOH extract of the leaves of Xanthium strumarium L. were found to have cytotoxic activities against five human tumor cell lines. Cytotoxicity-guided chromatographic fractionation led to the isolation of the ${\alpha}-methylene$ containing sesquiterpenes, xanthatin, 8-epi-xanthatin and 8-epi-tomentosin. 8-epi-Xanthatin was found to be far more cytotoxic than 8-epi-tomentosin, which lacks the conjugated enone moiety present in 8-epi-xanthatin.

• Journal of Photoscience
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• v.12 no.2
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• pp.109-111
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• 2005

It was found that 1,4-diketones such as 1,4-diphenyl-l,4-butanediones containing N,N-dimethylaminophenyl (pDPB) and N,N-dimethylaminonaphthyl (nDPB) at C2 are converted into 3-(4-dimethylaminoaryl)-1-phenylpropan-lones (pPPA and nPPA) by treatment with $Ca(OH)_2$ in methanol, which was easily oxidized to enone, i.e., 3-(4-dimethylaminophenyl)-l-phenylpropenones (pPPE and nPPE), when treated with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) in dichloromethane.

• Bulletin of the Korean Chemical Society
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• v.32 no.4
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• pp.1146-1152
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• 2011

The discovery of 2'-spirocyclopropyl-ribocytidine (J. Med. Chem. 2010, 53, 8150-8160) as a potent inhibitor of RNA synthesis by NS5B ($IC_{50}=7.3{\mu}M$), the RNA polymerase encoded by hepatitis C Virus (HCV), has led to the synthesis and biological evaluation of several carbocyclic versions of 2'-spiropropyl-nucleosides. The cyclopentenol intermediate 7 was successfully constructed via ring-closing metathesis (RCM) from divinyl 6. Spirocyclopropanation of enone 8 was effected by using (2-chloroethyl)-dimethylsulfonium iodide and potassium tert-butoxide to form the desired intermediate 9. The synthesized nucleoside analogues 21-24 were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line. Among them, the cytosine nucleoside analogue 22 exhibited significant anti-HCV activity ($EC_{50}= 8.2{\mu}M$).

• Bulletin of the Korean Chemical Society
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• v.34 no.3
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• pp.936-942
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• 2013

Series of (E)-1-aryl-3-(2-pyrrolyl)-2-propenones, that were aldol condensation products between pyrrole-2-carbaldehyde and m- and p-substituted acetophenones, were prepared and their $^1H$ and $^{13}C$ NMR spectra were examined to obtain the information on the conformation of the enone system. Similar studies were carried out with (E)-3-aryl-1-(2-pyrrolyl)-2-propenones that were prepared from 2-acetylpyrrole and m- and p-substituted benzaldehydes. The substituent chemical shifts were studied by applying the Hammett relationship.

• Natural Product Sciences
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• v.19 no.4
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• pp.355-359
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• 2013

A new monoterpene, crocusatin M (1), was isolated from the flower buds of Buddleja officinalis, together with four known monoterpenes, (6R)-hydroxy-1,1,5-trimethylcyclohex-4-enone (2), (+)-dehydrovomifoliol (3), 7-epiloliolide (4), and crocusatin D (5). Their structures were determined by an extensive analysis of 1D, 2D NMR, HRESI-MS, and CD data as well as by comparison of their spectroscopic data with those of literatures. All isolates were evaluated for inhibitory activities on LPS-induced nitric oxide production in RAW 264.7 cells. Among them, compounds 2 and 3 showed moderate inhibitory effects with $IC_{50}$ values of 63.8 and 24.4 ${\mu}g/ml$, respectively.