• Bulletin of the Korean Chemical Society
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• v.14 no.4
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• pp.497-499
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• 1993

Irradiation of 4-biphenylyl-4-methyl-2-cyclohexenone (5) in benzene or methanol produced trans-6-biphenylyl-5-methylbicyclo[3,1,0]hexan-2-o ne (5a) and 3-biphenylyl-4-methylcyclohex-2-enone (5b). Electronic configurations of the excited states for 5a and 5b were assigned as n, ${\pi}^*$ and ${\pi}$, ${\pi}^*$ triplet states respectively. Irradiation of 4-methyl-4(${\beta}$-naphthyl)-2-cyclohexenone in benzene or methanol gave 4-methyl-3-(${\beta}$ -naphthyl)-2-cyclohexenone (6a), which is thought to arise from ${\pi}$, ${\pi}^*$ triplet state.

• Bulletin of the Korean Chemical Society
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• v.13 no.3
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• pp.225-226
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• 1992

• Archives of Pharmacal Research
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• v.8 no.1
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• pp.21-30
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• 1985

Examination of the constituents of a marine sponge, Aplysina fishtularis, indicated that brominated tyrosine metabolites were mainly responsible for antimicrobial and antineoplastic activities. Halogenated tyrosine metabolites, 2, 6-dibromo-(2), 2-bromo-3-chloro-(3) and 2, 6-dibromo-(5), 5-a mino-2-bromo-6-chloro-(6) and 5-amino-2, 6-dich-loro-(7) 4-hydroxy-2-cyclohexenone-4-acetic acid lactams were identified as the major antineoplastic and antimicrobial principles. Many other brominated tyrosine metabolites were also confirmed, but they did not show antimicrobial and antineoplastic activities.

• Journal of the Korean Chemical Society
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• v.36 no.6
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• pp.925-932
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• 1992

Total synthesis of 9,10-dideoxyrhodomycinone(30) which is the late-stage precursor of naturally occuring ${\beta}$-rhodomycinone(1) is described. After phthalide sulfone 4 was converted to naphthalide sulfone 12 by the several step. Michale addition of naphthalide sulfone 12 which was converted to an anion with 5-ethyl-1,3-cyclohexenone(21) gave a good yield of linearly condensed tetracyclic ketone compound 26. The keto group of 26 was reduced with sodium borohydride and protected by methyl group to afford compound 28. 9,10-Dideoxy-${\beta}$-rhodomycinone(30) was synthesized from pentamethoxy tetracyclic compound 28 by oxidative demethylation and demethylation of 29.

• Journal of Photoscience
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• v.11 no.32
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• pp.77-81
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• 2004

Deoxygadusol (DO) and structurally related mycosporine-like amino acids, i.e. mycosporine glycine (MO) and mycosporine taurine (MT), were isolated from phytoplankton Prorocentrum micans and studied for the reactivity toward singlet oxygen. These water-soluble compounds with a cyclohexenone chromophore were all shown to be highly effective in quenching singlet oxygen ($^1$ $O_2$), with the efficiencies being significantly larger compared with histidine, a well-known $^1$ $O_2$ quencher. The $^1$ $O_2$ reaction rate constant ( $k_{Q}$) of DG was determined to be 5.4 ${\times}$ 10$^{7}$ $M^{-1}$ $s^{-1}$ by a steady state method based on competitive inhibition of rubrene oxidation. The feasibility of this method was confirmed by estimating the $k_{Q}$ values for MG and two other quenchers, furfuryl alcohol and 1,4-diazabicyclo [2,2,2]octane, and comparing with those values determined by the time-resolved $^1$ $O_2$ decay method in the previous work.ork.

• Journal of the Korean Chemical Society
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• v.29 no.1
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• pp.61-66
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• 1985

The preparation of 2-(2,2,2-trichloroethylidene)cyclohexanone(1), as a key compound for synthesizing 2-substituted 5,6,7,8-tetrahydro-3-cinnolinones, was attempted by the enamine condensation of cyclohexanone with chloral. However, the condensation of 1-morpholino-1-cyclohexene (2) with chloral afforded 2-(1-hydroxy-2,2,2-trichloroethyl) cyclohexanone (3), and its dehydration led to 2-(2,2-dichlorovinyl)-2-cyclohexenone (4). 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones could be synthesized using morpholinium ${\alpha}$-(4-morpholinyl)-${\alpha}$-(2-oxocyclohexyl)-acetate (5) in place of 1 with arylhydrazines.

• Bulletin of the Korean Chemical Society
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• v.30 no.1
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• pp.188-192
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• 2009

New $\alpha$-pyrones (1 and 2) and cyclohexenones (13 and 14) were isolated along with known analogues (3, 5−12) from the ethyl acetate extract of the whole broth of the fungus Paecilomyces lilacinus, a strain derived from a marine sponge Petrosia sp. Their structures were established by interpretation of 1D and 2D NMR, and FABMS data. It is interesting to isolate cyclohexenone derivatives from the genus Paecilomyces (family Trichocomaceae, order Eurotiales), since these cyclohexenones were previously reported only from far distinct genera, Phoma and Alternaria (family Pleosporaceae, order Pleosporales). Compounds 6, 7, and 9 were evaluated for cytotoxicity against a small panel of human solid tumor cell lines. Their cytotoxicity was insignificant upto a concentration of 30 ${\mu}g/mL$.

• Journal of the Korean Chemical Society
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• v.11 no.3
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• pp.111-116
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• 1967

A new alkaloid named Spirajine(m.p. 182~$184^{\circ}C$ $[{\alpha}]d^{19}+3.4^{\circ}$ in $CHCl_3$, $C_{23}H_{33}NO_3$, colorless prism) was isolated from the leaves of Spiraea Koreana Nakai (Spiraeceae) (Korean name "Chamjopab namu") which grows in the mountaineous area of Korea, by process of Scheme I (yields 0.13%). Another two unidentified alkaloids (not yet crystallized) were separated by the method of thin layer chromatography. (The Rf values of the two unidentified alkaloids were 0.66, 0.77, respectively and Spirajine 0.72) Spirajine were subjected to the structural investigation with the use of ultra violet and infra red spectrophotometry, and opical rotatory dispersion. The alkaloid contains two ketonic carbonyl groups, tertiary hydroxyl group, methyl groups, N-methyl group and both cyclohexane ring and cyclopentane ring.

• The Korean Journal of Pesticide Science
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• v.11 no.1
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• pp.1-7
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• 2007

We have developed an efficient synthesis of 2(5H)-furanones using the microwave-promoted Suzuki-Miyaura coupling reaction and evaluated their fungicidal activities against six fungal pathogens in vivo. In addition, 2-cyclopentenones or 2-cyclohexenones possessing one or two additional methylene groups instead of the oxygen in the 2(5H)-furanone skeleton were also prepared by using the similar method. As the results of in vivo fungicidal screening against 6 plant diseases, a few derivatives displayed specific fungicidal activities against rice blast and tomato late blast. Further studies toward the optimization of the chemical structures are necessary for the development of novel fungicides with high potency.