• 약학회지
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• 제47권6호
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• pp.417-421
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• 2003

This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

• Journal of Pharmaceutical Investigation
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• 제22권3호spc1호
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• pp.49-63
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• 1992

Two different types of chemical manipulations of dobutamine were investigated in order to develop novel, improved cardiotonic drugs. Three new analogues of carbostyril, in which the m-hydroxy group of dobutamine was isosterically modified with an amide type carbostyril system, were synthesized from, ${\rho}-methoxyphenethylamine$ via multi-steps. Two analogues of (2'-aminoethyl)-1-hydroxy-2-pyridone system which has isosteric structural similarity with dopamine without having the COMT vulnerable m-hydroxy group were synthesized via 12 synthetic steps. Their biological stabilities in various media and inotropic activities were evaluated.

• Archives of Pharmacal Research
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• 제18권6호
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• pp.440-448
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• 1995

Fitty two flavones were synthesized from polyoxygenated dibenzoylmethanes which were obtained by a modified Baker-Venkatarman rearrangement, of 2-benzoyl oxyacetophenones. The following flavones among them showed good cytotoxic activities against L1210 and HL60 cells ; 2'-benzoyloxy-5,7-dimethoxyflavone $(8.2{\mu}g/ml,{\;}5.0 {\mu}g/ml)$, 2'-benzyloxy-5,7,8-trimethoxyflavone $(5,9 {\mu}g/ml,{\;}11.0{\mu}g/ml,{\;}2.7{\mu}g/ml)$, 2'-hydroxy-5,7,8-trimethoxyflavone $(9.8{\mu}/ml,{\;}6.2{\mu}g/ml)$, 2'-benzyloxy-5-hydroxyflavone $(5.2 {\mu}g/ml,{\;}3.6{\mu}g/ml)$, and 5,2'-dihydroxyflavone $(5.1{\mu}g/ml,{\;}4.0{\mu}g/ml)$. Presence of 5-methoxy group potentiated the cytotoxic activity, while the existence of 7-methoxy group decreased the activity. 5-Hydroxy or methoxy activates 4-carbonyl group, while 7-methoxy group deactivates the acrbonyl group. From these observation it was concluded that the activation of carbonyl group at C-4 of a flavone is important for the enahncement of the cytotoxic activity. The presence of both 5-hydroxy and 2-benzyloxy-or 2-hydroxy group enhanced the antitumor activity; 2'-benzyloxy-5-hydroxy-7-methoxyflaone 9T/C=144%), 5.2'-dihydroxy-7-methoxyflavone (T/C=132%) and 5,2'-dihydroxy-6,78,6' trtramethoxyflvone (T/C = 172%) 2'hexanolytion of 5,2'-dihydroxy-flavones did not improve the natitumor activity; 2' hexanoyloxy-5-hydroxy-7-methoxyflavone showed T/C = 132%, about the same as that of 5,2'-dihydroxy-7-methoxyflvone (T/C=130%)

• 약학회지
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• 제37권1호
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• pp.36-40
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• 1993

The 4-(2'-(N-(l-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-l- hydroxy-2-pyridone which has isoelectronic and isosteric structural similarity with dobutamine without having the Catechol-O- Methyltransferase(COMT) vulnerable m-hydroxy group was synthesized via 12 synthetic steps.

• 약학회지
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• 제55권5호
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• pp.367-373
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• 2011

It was reported that the potency of TMMC derivatives was related to the presence of the 2'-hydroxy group on the A ring. Also, 4-dimethylamino group on the B ring lowered the anti-inflammatory potency of the chalcones. We synthesized various derivatives of 2'-hydroxy chalcones having other substituents on B ring. The synthetic derivatives showed the more potent anti-inflammatory effect, comparable to that of the TMMC derivatives reported previously.

• 약학회지
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• 제47권6호
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• pp.450-455
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• 2003

Synthesis of (lR,5S,6S)-6-[(lR)-1-hydroxyethyl] -2-[(3S,5S)-5-(2-ethoxycarbonyl-1-moxy(hydroxy)iminoethyl)pyrrolidine-3-ylthio]-1-methylcarbapen-2-em-3-carboxylic acids (10a,l0b) were described. Methyl(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxyla late (I) was prepared from trans-4-hydroxy-L-proline with (2S,4R)-abs olute configuration as starting material. (2S,4S)-1-allyloxycarbonyl-2-(2-ethoxycarbonyl-hydroxy(methoxy )iminoethyl)-4-mercapto- pyrrolidines (6,7) were obtained from the tritylthio compound (I). (lR,5S,6S)-6-[(lR)-1-hydroxyethyl]-2-[(3S,5S)-5-(2-ethoxycarbonyl-1-methoxy(hydroxy)imino-ethyl)pyrrolidine-3-ylthio]-1-methylcarbapem-2-em-3-carboxylic acids (10a,10b) were obtained by the coupling reaction with carbapenem diphenylphosphates (8) and pyrrolidine-thiol moiety (6,7). Their in vitro antibacterial activities against both Gram-positive and Gram-negative were tested. Compounds ( 10a,10b) showed potent antibacterial activity except pseudomonas aerusinosa.

• Archives of Pharmacal Research
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• 제14권1호
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• pp.41-43
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• 1991

For the purpose of survey of the antibacterial activity against a cariogenic bacterium Streptococcus mutans OMZ 176 with the introduction of hydroxyl and allyl groups to o-phenylphenol (Fig. 2, 1), 4-hydroxy-o-phenylphenol (2), and 3,6-diallyl-4-hydroxy-o-phenylphenol (4) were synthesized, sucessively. The synthesized compounds, 2 and 4 showed more potent antibacterial activity than the starting material, 1. The hydroxyl group was supposed to the essential element for the antibacterial activity and the introduction of allyl group to phenolic ring to be another element to increase the activity.

• Journal of Applied Biological Chemistry
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• 제61권4호
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• pp.423-428
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• 2018

산해박 뿌리 정유 추출물에 대한 장내 미생물 5종(Bifidobacterium bifidum, B. longum, C. perfringens, E. coli 및 L. casei)의 항균활성 및 작은소피참진드기(Haemaphysalis longicornis)의 살비활성을 검정하였다. 산해박 정유는 20.0 mg/disc에서 유해균 2종(C. perfringens 및 E. coli)에 대해 항균활성을 확인하였으나, 작은소피참진드기에는 살비활성을 나타내지 않았다. GC-MS 분석을 통해 얻어진 구성성분 중에 2'-hydroxy-5'-methoxyacetophenone이 유해균 2종에 대해서 10.0 mg/disc에서 각각 12.1 및 12.0 mm의 inhibition zone이 나타난 것을 확인하였다. 이와 같은 결과로 인하여 2'-hydroxy-5'-methoxyacetophenone 유도 화합물들의 구조에 따른 항균활성을 검정하고자 acetophenone 계열 유도체 10종(acetophenone, 2'-hydroxyacetophenone, 4'-hydroxyacetophenone, 2'-methoxyacetophenone, 4'-methoxyacetophenone, 2',4'-dihydroxyacetophenone, 2',5'-dihydroxyacetophenone, 2',4'-dimethoxyacetophenone, 2',5'-dimethoxyacetophenone 및 2'-hydroxy-4'-methoxyacetophenone)과 비교 실험한 결과, methyl group이 포함된 acetophenone 유도화합물에서는 유해균 2종에 대해 항균활성을 나타내었으며, 장내유익균에 대해서는 영향을 미치지 않았다. 그러나 hydroxyl group이 포함된 acetophenone 유도화합물에서는 장내 미생물에 대해 항균 활성이 전혀 나타내지 않았다. 이상의 결과를 통해 산해박 정유와 구성성분 2'-hydroxy-5'-methoxyacetophenone 및 그 유도체는 천연 장내 세균총 개선제로서의 가능성을 제시하였다.

• 약학회지
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• 제44권3호
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• pp.279-282
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• 2000

The inhibition mode of S-hydroxy-2-phenylalanylaminomethyl-4-pyron ($IC_{50}=24.6{\;}{\mu}M$) on mushroom tyrosinase was investigated using L-tyrosine as a substrate. This inhibitor is the kojic acid derivative, where the C-7 hydroxyl of kojic acid was replaced by amino group and coupled to the carboxyl of L-phenylalanine. The kinetic data obtained show a competitive inhibition pattern.

• Archives of Pharmacal Research
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• 제21권6호
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• pp.703-706
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• 1998

The anticomplementary activity of stilbenes from medicinal plants in Korea was investigated in vitro. 3,5-Dihydroxy-4'-methoxystilbene (3) was most potent with $IC_{50}$ value of $1.5{\times}10^{-4}M$ followed by rhapontigenin (4), oxyresverastrol (2), 2,3,4',5-tetrahydroxystilbene-2-O-beta-glucoside (9), rhaponticin (8), resverastrol (1), and piceid (7). The activity was found to be increased by a methylation on a hydroxy group of C-4' of 1, but decreased by further methylation on hydroxy groups of C-3 and C-5 and glucosylation on any hydroxy group of 1. Addition of hydroxy group on C-2' of 1 or C-3' of 3 was little affected on the anticomplementary activity but the activity was increased by O-glucosylation on C-2 of 1.