• Bulletin of the Korean Chemical Society
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• 제27권9호
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• pp.1359-1363
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• 2006

Novel anthracycline analogues 2-9 as potential anticancer agents were synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2, 6, and 7 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a sodium lactate, and stearic acid, respectively. Compounds 3-5 and 7-9 were prepared by the reaction of either daunomycin (1a) or doxorubicin (1b) with L-lactic and stearic acids in the presence of EDCI/PP reagents.

• 약학회지
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• 제46권6호
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• pp.381-386
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• 2002

The synthesis of new 6-exomethylene sulbactam derivatives with 5-methyl-1,3,4-thiadiazole was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylen penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6-10 were deprotected by AlCl$_3$ and neutralized with NaOH solution to give the sodium salts 11-15.

• Bulletin of the Korean Chemical Society
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• 제23권9호
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• pp.1241-1255
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• 2002

Series of m- and p-substituted benzyl derivatives of pyrrole, tetramethyl 1-benzyl-3a,7a-dihydroindole-2,3,3a,4-tetracarboxylate, and trimethyl 1-benzylindole-2,3,4-tricarboxylate were prepared and their 13C NMR spectra were obtained in 0.1 M solutions of chloroform-d. Both single substituent parameter and dual substituent parameter analyses were carried out to correlate the substituent chemical shifts. The ${\beta}$ carbon of the indole series showed the most profound substituent effect dependence as well as the best correlation. The results are explained by the hyperconjugation of the benzyl methylene group.

• Macromolecular Research
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• 제11권6호
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• pp.501-505
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• 2003

Poly(l,6-heptadiyne) derivatives with phenoxy and 3,7-dimethyloctyloxyphenoxy substituents were synthesized using metathesis polymerization. Polymerizations using MoCl$\sub$5/ as the sole catalyst gave high yields and the resulting polymers were completely soluble in organic solvents. The polymers' structures and thermal properties were characterized using NMR and UV-Vis spectroscopy, as well as with TGA and DSC thermograms. From the analysis of the high-resolution $\^$13/C-NMR spectra, we was found that these polymers contain six-membered rings. The number-average molecular weights and polydispersities of the polymers were ca. 7.0∼20 ${\times}$ 10$^3$ and 3.1∼5.8, respectively. The glass transition temperatures of the polymers were found to be in the range 91∼159$^{\circ}C$.

• Bulletin of the Korean Chemical Society
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• 제35권7호
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• pp.2123-2129
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• 2014

Pim kinases are promising targets in the treatment of hematopoietic and solid cancers. Meridianin C was chosen as a starting point to discover novel pim kinase inhibitors. Using known pim kinase's structural information, aminopyrimidine was introduced to provide the hydrogen-bonding interactions with the conserved lysine residue in the ATP binding pocket of all three Pim kinases. Synthesized 3,5-bis(aminopyrimidinyl)indole derivatives showed pan-pim inhibitory activity. Aminoalkyl substituent was attached on the aminopyrimidine to further enhance the potency and physicochemical properties of compound. The research reveals a significative way of designing compounds with high potency and kinase selectivity for pan-pim kinases.

• Archives of Pharmacal Research
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• 제24권5호
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• pp.367-370
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• 2001

This study describes the synthesis and in vitro evaluation of noble 2-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-isoindolinone Derivatives for the inhibition of TNF-$\alpa$ production. Among these compounds, 2- [3- (Cyclopentyloxy)- 4- methoxyphenyll- 3- methyl -1 - isoindolinone (5) was the most potent in inhibitory activity of TNF-$\alpa$ production in LPS-stimulated RAW264.7 cells.

• Archives of Pharmacal Research
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• 제17권4호
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• pp.236-239
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• 1994

The suppressive activity of isoflavonoids against lymphocyte proliferation in vitro was examined. Isoflabvonoid derivatives tested were isflavones isolated from Pueraia radix and synthesized 7-O-substituted biochanin A derivatives. The certain isoflavones such as biochanin A and 2-carbethoxybiochainin A were found to possess the suppressive activity against concanavaline A (Con A)-induced lymphocyte proliferation from mouse spleen. Against mixed lymphocyte culture reaction, biochanin A, 2-carbethoxybiochainin A, daidzein, formononetin, genistein and 7-O-isopropylbiochaninl A showed the suppressive activity at $10^{-5}$ M. However, all isoflavones tested did not show the suppressive activity against lymphocyte proliferation induced by B-cell mitogen, lipopolysaccharide (LPS). In general, isoflavones were revealed to be less active than flavones/flavonols.

• 생약학회지
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• 제44권1호
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• pp.6-9
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• 2013

Two fraxinellone-based hydrogenated derivatives were prepared from fraxinellone, a well-known degraded limonin, via catalytic hydrogenation in the presence of $PtO_2$ in HOAc. Their structures were confirmed as (3S,3aR,3'R)-3a,7-dimethyl-3-(tetrahydrofuran-3-yl)-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one and (3S,3aR,2'R)-3-((R)-1-hydroxybutan-2-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one on the basis of 2D NMR assignments. The $^{13}C$ NMR assignments of two quaternary carbons in the ${\alpha}$,${\beta}$-unsaturated carbonyl moiety of ${\gamma}$-butyrolactone core of fraxinellone should be revised.

• Journal of Microbiology and Biotechnology
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• 제20권3호
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• pp.510-512
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• 2010

A series of thiobarbituric acid derivatives were constructed and evaluated for inhibitory activity on hepatitis C virus NS5B polymerase. In biochemical assays using purified viral polymerase and RNA template, the $IC_{50}$ value was improved to 0.41 ${\mu}M$ from the original compound's 1.7 ${\mu}M$ value. In HCV sub genomic replicon assay, the $EC_{50}$ value was improved to 3.7 ${\mu}M$ from the original compound's 12.3 ${\mu}M$ value. $CC_{50}$ was higher than 77 ${\mu}M$ for all compounds tested, suggesting that they are useful candidates for anti-HCV therapy.

• Archives of Pharmacal Research
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• 제22권1호
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• pp.18-24
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• 1999

Various flavonoid derivatives were previously reported to possess the inhibitory activity on cyclooxygenase/lipoxygenase. And these properties of flavonoids might contribute to their anti-inflammatory activity in vivo. In this study, several polyhydroxylated/methoxylated flavonoid derivatives such as oroxylin A. wogonin, skullcapflavone II, tectorigenin and iristectorigenin A were isolated from the medicinal plants. these compounds were evaluated fro their inhibitory effects on cyclooxygenase/lipoxygenase from the homogenate of human platelets in vitro. It was found that isoflavones including daidzein and tectorigenin possessed the inhibitory activity on cycloooxygenase, although the potency of inhibition was far less than that of indomethacin. In addition, oroxylin A, baicalein and wogonin inhibited 12-lipoxygenase activity without affecting cyclooxygenase, which suggested that 5,6,7- or 5,7,8-trisubstitutions of A-ring of flavone gave favorable results. The IC50 values of oroxylin A and NDGA against 12-lipoxygenase were found to be 100 and 1.5 uM, respectively.