• 약학회지
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• 제60권3호
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• pp.135-140
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• 2016

Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone, which is associated with stabilization of many oncogenic proteins for cancer cell survival. Hsp90 is overexpressed 2-10 fold higher in cancer cells than normal cells. Due to its potential to simultaneously disable multiple signaling pathway, Hsp90 has been identified as a validated target for cancer therapy. Accordingly, we designed and synthesized 2',4'-dimethoxychalcone derivatives to inhibit Hsp90 chaperone function. Among 2',4'-dimethoxychalcone derivatives, we found that compound 1g disrupted Hsp90 chaperoning function and impaired the growth of cancer cells. These findings indicated that 1g could serve a potential lead compound to target Hsp90 in cancer chemotherapy.

• Biomolecules & Therapeutics
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• 제17권4호
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• pp.422-429
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• 2009

Invasion and metastasis is the main cause of cancer mortality. Angiogenesis is a prerequisite for the tumor growth and metastasis. Matrix metalloproteinases (MMPs) are the key enzymes playing in the invasive growth and metastasis of cancer as well as angiogenesis. Xanthohumol, a prenylated chalcone of the Hop plant (Humulus lupulus L), has been reported to suppress cancer invasion and angiogenesis. In the present study, we investigated the antiinvasive effects of xanthohumol (1) and its synthetic derivatives, 4'-O-methylxanthohumol SEM ether (2), xanthohumol C (3), and xanthohumol C MOM ether (4) in relation to MMP expression in HT-1080 human fibrosarcoma cells. The compound 1 and its derivative, 3 and 4, significantly inhibited serum-induced HT-1080 cell invasion, and 12-O-tetradecanoylphorbol-13-acetate (TPA)-enhanced activity and expression level of MMP-2 and MMP-9 in a concentration-dependant manner. In addition, they inhibited TPA-enhanced expression of MT1-MMP with relatively weak inhibition in tissue inhibitor of metalloproteinase (TIMP)-1 and TIMP-2 level. The compound 1 significantly decreased the cell viability, whereas the derivatives, 2 and 3 showed no cytotoxicity, and compound 4 showed slight cytotoxicity in the cells. Furthermore, in a chick chorioallantoic membrane (CAM) assay, the derivatives 3 and 4 dose-dependently suppressed vascular endothelial growth factor (VEGF)-induced angiogenesis, which is similar to that of compound 1. Taken together, the results indicate that compounds 3 and 4 may be valuable anti-angiogenic agents in the treatment of chronic diseases such as cancer and inflammation working through suppression of MMP-2 and MMP-9.

• Archives of Pharmacal Research
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• 제16권1호
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• pp.25-28
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• 1993

Our previous report demonstrated that certain flavonoid aglycones such as apigenin (flavone), quercetin, morin (flavonols), and biochanin A (isoflavone) showed in vivo antiinflammatory activity via topical and oral routes of adminstation. As a continual study, the various flavonoid glycosides have been evaluated in mouse ear edema assay using archidonic acid or croton-oil as a inflammagen. Flavonoids were orally administered (2 mg/mouse) and ear edema inhibition was measured. Significant antiinflammatory activities were found esepcially in flavone and flavonol glycosides (15-29% inhibition) although the flavonoid derivatives tested showed less antiinflammatory activity than hydrocortisone or indomethacin. Chalcone and flavanone derivatives were not significantly active. And in general, flavonol glycosides of kaempferol-type were found to have a higher oral antiinflammatory activity than that of flavonol glycosides of quercetin-type in mice.

• Bulletin of the Korean Chemical Society
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• 제31권3호
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• pp.664-669
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• 2010

This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.

• 대한화학회지
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• 제55권5호
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• pp.776-780
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• 2011

A mild and efficient procedure for the synthesis of various 1,5-benzothiazepines were developed. This method provides an easy access for preparation of 1,5-benzothiazepine derivatives in the presence of 10 mol% catalyst of CAN under ultrasonic irradiation. This method provided clean conversion, mild reaction condition, no use of toxic solvent and shorter reaction time compared to other reported method.

• Bulletin of the Korean Chemical Society
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• 제28권12호
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• pp.2338-2343
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• 2007

Under the framework of green chemistry, an efficient and extremely fast procedure for the synthesis of 5a-h through four-step procedure starting from 2-arylidenetetralin-1-one 1a-d under microwave irradiation is described. A considerable increase in the reaction rate has been observed with better yield. The structures of the synthesized compounds have been characterized on the basis of their elemental analysis and spectral data. Synthesized compounds 5a-h was evaluated for their antimicrobial activity. Some of the compounds exhibited appreciable activity.

• Bulletin of the Korean Chemical Society
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• 제31권11호
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• pp.3180-3182
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• 2010

A simple facile 'one pot' synthesis of 2-amino-3-cyano-4,6-diarylpyridine derivatives via three component reaction of chalcone, malanonitrile and ammonium acetate under ultrasonic irradiation and grindstone technology. All the synthesized compounds have been characterized on the basis of their elemental analyses and spectral data (IR, $^1H$ NMR, $^{13}C$ NMR and Mass).