• 약학회지
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• 제56권3호
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• pp.186-190
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• 2012

Nuclear factor-${\kappa}B$ (NF-${\kappa}B$) has been considered as one of the major targets for therapeutic agents of diverse human diseases. In the previous studies, 6-hydroxy-7-methoxychroman-2-carboxylic acid N-phenylamide (KL-1156) and chroman-2-carboxylic acid N-(4-chlorophenyl)amide were identified as good inhibitors of NF-${\kappa}B$ activation. In this continuous study, we describe the synthesis and NF-${\kappa}B$ inhibitory activities of chroman derivatives containing N-heteroaryl groups for exploration of SAR (structure-activity relationship). In addition, inhibitory effects of cell proliferation are evaluated against human cancer cell lines (NCI-H23 and PC-3).

• 약학회지
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• 제54권3호
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• pp.200-204
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• 2010

Nuclear factor-${\kappa}B$ (NF-${\kappa}B$) plays critical roles in physiological and pathological processes such as immune function, cellular growth, homeostasis, apoptosis, and inflammation. As part of our ongoing efforts to develop novel NF-${\kappa}B$ inhibitory agents, we reported that KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenylamide) exhibited potent inhibitory activity of NF-${\kappa}B$. For further structure-activity relationship, a series of 7-aryloxy-chroman-2-carboxylamide derivatives were synthesized to explore their inhibitory activities of NF-${\kappa}B$.

• 약학회지
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• 제57권6호
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• pp.426-431
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• 2013

In our previous studies, 6-hydroxy-7-methoxychroman-2-carboxylic acid N-phenylamide (KL-1156) was identified as a good inhibitor of nuclear factor-${\kappa}B$ (NF-${\kappa}B$) activation. In continuation of our study, we describe the structure-activity relationship of chroman derivatives containing N-arylalkyl groups and their NF-${\kappa}B$ inhibitory activities. In addition, inhibitory effects of cell proliferation are evaluated against human cancer cell lines (NCI-H23 and PC-3). The most active compounds 3i and 3j contained diphenylethyl and diphenylpropyl side chain on amide nitrogen.

• Bulletin of the Korean Chemical Society
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• 제35권6호
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• pp.1625-1632
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• 2014

A concise and efficient one-pot synthesis of chroman-2,4-dione-based HKA derivatives by three component reaction of HKAs, triethoxymethane and 4-hydroxycoumarin derivatives under solvent-free and catalyst-free conditions is described. This protocol has many advantages, in that the GAP (Group-Assistant-Purification) chemistry process is involved in this method. As a result, the experimenter can avoid cumbersome process steps such as traditional chromatography and recrystallization purifications. The desired products can be easily obtained by washing the crude products with 95% EtOH.

• Applied Biological Chemistry
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• 제35권6호
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• pp.470-474
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• 1992

해양환형동물 thelepus setosus로부터 분리된 thelepin ${\underline{2}}$의 항균활성에 착안하여 새로운 항균성 선도구조를 찾아내고자, B 환구조를 coumaran형에서 chroman-4-one형으로 전환하고 생물활성을 조사하였다. Thelepin의 spirobenzopyranone 유도체를 산화적분자내에 환반응을 이용하여 합성하였으며 진균 2종과 박테리아 2종을 대상으로 paper disc법으로 생물활성을 조사한 결과 gram-positive 박테리아인 Bacillus subtilis에 대하여 $5\;{\mu}g/disc$ 수준에서 억제 활성을 보였다.

• Bulletin of the Korean Chemical Society
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• 제32권12호
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• pp.4163-4164
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• 2011

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 2008년도 Proceedings of the Convention
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• pp.160-160
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• 2008

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.232.2-232.2
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• 2003

Many neurodegenerative disorders such as stroke, Alzheimer's disease, and Parkinson's disease have been known to be associated with an excessive generation of reactive oxygen species (ROS) and oxidative stress. Therefore, the antioxidants have recently received much attention as therapeutic agent for the treatment of neurodegenerative disease. (omitted)

• 약학회지
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• 제50권5호
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• pp.322-325
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• 2006

In the course of developing novel antioxidants, we synthesized four of 6-hydroxy-7-methoxy-4-oxochroman-2carboxylic acid dialkylamides (3a-d) $(13{\sim}18%)$ and four of 6-hydroxy-7-methoxychroman-2-carboxylic acid dialkylamides (4a-d) $(52{\sim}89%)$, incorporating the basic amine functionality. None of these compounds exhibited significant antioxidant activity possibly due to the hydrophilic character of the basic amine side chains.

• Bulletin of the Korean Chemical Society
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• 제30권2호
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• pp.415-418
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• 2009

Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (${\pm}$)-glabridin enantiomers were studied with synthetic glabridin. Synthetic glabridin enantiomers were separated by semi-preparative Sumi-chiral column chromatography, and characterized by UV-Vis and NMR spectroscopy. Three-dimensional molecular structure of glabridin was obtained as equatorial Ph-3 half chair chroman ring from semi-empirical PM3 calculation, and refined by coupling constants in $^1H$ NMR spectrum. Finally, absolute configurations of two enantiomers were determined by circular dichroism spectroscopy based on the empirical helicity rules. Absolute configuration of natural (+)-glabridin was confirmed as (R)-glabridin, as known.