• Proceedings of the PSK Conference
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• 2003.04a
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• pp.252.3-252.3
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• 2003

An effective and convenient regioselective reduction of 5-benzylidene 2,4-thiazolidinedione derivatives to the corresponding 5-benzyl 2,4-thiazolidinedione derivatives has been accomplished using 3,5-dicarboethoxy-2,6-dimethyl-1,4-dihydropyridine (Hantzsch dihydropyridine ester: HEH) with silica gel as an acid catalyst in a good yield.

• The Sea:JOURNAL OF THE KOREAN SOCIETY OF OCEANOGRAPHY
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• v.17 no.1
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• pp.9-15
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• 2012

Worldwide development of harmful algal blooms causes serious problem for public health and fisheries industries. To evaluate the algicidal impact on the harmful algae bloom species in aquatic ecosystems of coast, a new algicide thiazolidinedione derivative (TD49) were tentatively examined in the growth stages (i.e., lag, logarithmic and stationary phase) of rapidophyceae $Heterosigma$ $akashiwo$, $Chattonella$ $marina$ and $Chattonella$ sp..Three strains could easily destroy in the lag phase due to relatively weak cell walls than those of the logarithmic and stationary phase. It is thought that inoculation of TD49 substances into initial or developmental natural blooms with a threshold concentration ($2{\mu}M$) can maximize the algicidal activity. Also, bio-chemical assays revealed that the algicidal substances from all culture strains were likely to be extracellular substances because those cells have easily destroyed in cell walls. On the other hand, natural zooplankton communities were influenced within the exposure experiments of $2{\mu}M$, which is showed the maximum algcidal activity of tested organisms. These results indicate that although the TD49 substance is potential agents for the control of $H.$ $akashiwo$, $C.$ $marina$ and $Chattonella$ sp. in the enclosed eutrophic bay and coastal water, more detailed research of acute toxicity effect on high trophic organism in marine ecosystems need to be conducted.

• Archives of Pharmacal Research
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• v.27 no.11
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• pp.1099-1105
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• 2004

The peroxisome proliferator-activated receptors (PPARs) are a primary regulator of lipid metabolism. Potency for activation of PPAR$\gamma$, one of a subfamily of PPARs, particularly mirrors glucose lowering activity. We prepared thiazolidinediones featuring benzoxazole moiety for subtype selective PPAR$\gamma$ activators. 5-[4-[2-(Benzoxazol-2-yl-alkylamino)ethoxy]benzyl]thiazolidine-2,4-diones have been prepared by Mitsunobu reaction of benzoxazolylalkylaminoethanol 8 and hydroxybenzylthiazolidinedione 6 and their activities were evaluated. Most compounds tested were identified as potent PPAR$\gamma$ agonists.

• Proceedings of the Korean Society of Applied Pharmacology
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• 2003.11a
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• pp.118-118
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• 2003

The use of PPARν (peroxisome proliferator activated receptor ν) activators in the treatment of type 2 diabetes is well established due to their ability to lower blood glucose and insulin levels and omprove insulin sensitivity. Thiazolidinedione analog is one of the potential antidiabetic drug that binds and activates PPARν selectively. In an effort to develop novel and effective antidiabetic thiazolidindione analogs, synthesis of tetrahydroquinoline and para-substituted benzene-linked thiazolidinedione analogs were carried out via coupling reaction of the hydrophobic segments with hydroxybenzylthiazolidinedione.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.186.2-186.2
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• 2003

PPARs (peroxisome proliferator activated receptors) are member of nuclear hormone receptors superfamily. Activations of PPARs upon binding with ligands modulate glucose metabolite, differentiation of adipocyte, inflammation response, and so on. Thiazolidinedione analog is one of the potential antidiabetic drug that binds and activates PPAR selectively and enhances insulin sensitivity. In an effort to develop novel and effective antidiabetic thiazolidindione analogs, we have synthesized tetrahydroquinoline and para-substituted benzene-linked thiazolidinedione analogs by coupling reaction of the hydrophobic segments with hydroxybenzylthiazolidinedione.

• KSBB Journal
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• v.26 no.1
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• pp.7-12
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• 2011

In order to perform an acute toxicity assessment of a new algicide, thiazolidinedione derivative (TD53) with enhanced solubility and lower toxicity to marine ecosystem, representative 3 organisms: plant plankton (Skeletonema costatum), animal plankton (Daphnia magna), fish (Paralichthys olivaceus) related in the food chain of marine ecosystem according to OECD standard methods were employed in the exposure experiment. The exposure assessment showed that $EC_50$ of S. costatum in 96-hour, $EC_50$ of D. magna in 48-hour and $LC_50$ of P. olivaceus in 72-hour for TD53 were $1.53\;{\mu}M$, $0.61\;{\mu}M$ and $2.14\;{\mu}M$ respectively. NOEC (No Observed Effect Concentration) and PNEC (Predicted No Effect Concentration) were calculated to be $0.25\;{\mu}M$ and 6.10 nM, respectively from $EC_50$ of most sensitive strain, D. magna. Comparing with the results of toxicity assessment previously performed by using Ulva pertusa Kjellman accepted as an ISO standard method, the values of PNEC showed 3.7 times lower toxicity in case of this study employing 3 organisms, indicating that if the organisms which are more representative and sensitive in marine ecosystem are further investigated, more accurately and validly predicted toxicity of TD53 could be applied in field.

• Ocean and Polar Research
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• v.34 no.2
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• pp.125-135
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• 2012

To evaluate the algicidal impact of a newly developed algicide thiazolidinedione derivative, TD49, on dinophyceae Akashiwo sanguinea in aquatic ecosystems, tentative culture experiments for the target species were conducted in small (SS), middle (MS), and large scale (LS) culture vessels. When TD49 was introduced at the final concentration of $2{\mu}M$ in SS and MS, as well as $1{\mu}M$ in LS, the abundance of A. sanguinea decreased significantly in all the treatments. On the other hand, total phytoplankton abundance, except A. sanguinea in the TD49 treatments, gradually increased with culture time, which implies that a cell destruction of A. sanguinea by TD49 is a major cause of the population growth by other phytoplankton species. Also, A. sanguinea was easily destroyed, which was likely to be a source of extracellular substances. In particular, a pH decrease was significant in the treatments than in the control, which indicates that the water in the treatments has been acidified, due to an increase in the heterotrophic metabolisms of bacteria and degradation of A. sanguinea cells. Our results indicate that the TD49 substance is the potential agents for the control of A. sanguinea in the enclosed and eutrophic water bodies.

• Proceedings of the Korean Society of Applied Pharmacology
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• 2003.11a
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• pp.117-117
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• 2003

PPARs (peroxisome proliferator activated receptors) are member of nuclear hormone receptors superfamily. Activations of PPARs upon binding with ligands modulate glucose metabolite, differentiation of adipocyte, inflammation response, and so on. Thiazolidinedione analog is one of potential antidiabetic drug that binds and activates PPARν selectively and enhances insulin sensitivity. In an effort to develop novel and effective antidiabetic thiazolidindione analogs, syntheses of benzoxazole and benzothiazole-linked thiazolidinedione analogs were performed via coupling reaction of benzoxazolylalkylaminoethanol with hydroxybenzylthiazolidinedione to develop novel and effective antidiabetic thiazolidindiones. All compounds were evaluated their biological potency by PPARν transactivation assay and revealed the similar potency with Troglitazone. However, lengthening of N-alkyl substituent did not seem to be beneficial for the activity.

• Bulletin of the Korean Chemical Society
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• v.32 no.7
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• pp.2171-2177
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• 2011

Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzyl-idinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of $K_2CO_3$ and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).

• Archives of Pharmacal Research
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• v.28 no.2
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• pp.142-150
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• 2005

The synthesis and structure-activity relationships of a novel series of substituted quercetins that activates peroxisome proliferator-activated receptor gamma ($PPAR{\gamma}$) are reported. The $PPAR{\gamma}$ agonistic activity of the most potent compound in this series is comparable to that of the thiazolidinedione-based antidiabetic drugs currently in clinical use.