• YAKHAK HOEJI
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• v.36 no.1
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• pp.12-16
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• 1992

A new method for the synthesis of alminoprofen, which is a non-steroidal antiinflammatory agent, was described. Ethyl 2-phenyl-propionate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl ${\alpha}-chloro-{\alpha}(methylthio)acetate(1)$, followed by methylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)propionate(6) was obtained by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl)propionate(5). Alminoprofen was synthesized by reaction of (6) with methallyl chloride, followed by hydrolysis of the resultant ethyl 2-(p-methylallylaminophenyl)propionate (7).

• YAKHAK HOEJI
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• v.35 no.5
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• pp.389-393
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• 1991

A convenient method for the synthesis of indobufen, which is a potent antiinflammatory agent, was described. Ethyl 2-phenylbutyrate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl $\alpha$-chloro-$\alpha$-(methylthio)acetate(l) followed by ethylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)butyrate(6) was prepared by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl) butyrate(5). Indobufen was obtained by condensation reaction of (6) with phthalic anhydride followed by reduction and hydrolysis of the resultant ethyl 2-[p-(1, 3-dioxo-2-isoindolinyl)phenyl]butyrate(7).

• Archives of Pharmacal Research
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• v.12 no.1
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• pp.52-57
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• 1989

The structure of cinmetacin was determined by single crystal X-ray diffraction analysis. The compound was recrystallized from a mixture of acetone and water in orthorhombic, space group $P2_12_12_1$, with Z=4, a=35.681(8), b=9.482(2), c:5.071(1) ${\AA}$, $D_x=1.352 g/cm^3$, and $D_m=1.35g/cm^3$. The structure was solved by direct method and refined by least-squares procedure to the final R value of 0.036 for 1441 observed reflections ($F{\geq}3{\sigma}(F)$). The carboxyl group of the molecule is nearly perpendicular to the indole ring. The dihedral angle between indole ring and phenyl group is $64.5^{\circ}$. The molecules are linked together via O(1)-H ----O(3) hydrogen bonds, and arranged along 2-fold screw axis in the crystal. The intermolecular contacts are the normal van der Waals' forces.

• Archives of Pharmacal Research
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• v.11 no.2
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• pp.127-133
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• 1988

The crystal structure of fenbufen was determined by X-ray diffraction techniuques. The compound was recrystallized in orthorhombic crystal system, space group $Pca2_1$ a = 31. 918(10), b = 5.550 (2), c = 15.078 (9) ${\AA}, D_m$= $1.26, {\D_x$= 1.264 g/$\textrm{cm}^3$, and Z = 8. The structure was solved by direct methods and refined by least squares procedure to the final R value of 0.051 for 1780 independent reflections. Two molecules in the asymmetric unit are related by a pseudo center of symmetry and dimerized via O-H...O hydrogen bonds. The carbonyl group attached to the phenyl ring is nearly coplanar to the ring. In the crystal the molecules are arranged in paralle stacks in the a direction.

• YAKHAK HOEJI
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• v.36 no.4
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• pp.341-344
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• 1992

A facile method for tolmetin, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of 1-methylpyrrole with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ (1) gave ethyl ${\alpha}-methylthio$-1-methyl-2-pyrroleacetate (4), which was readily converted into ethyl 1-methyl-2-pyrroleacetate (5) by reductive desulfurization with zinc dust in acetic acid. Tolmetin was synthesized by Friedel-Crafts acylation of (5) with p-toluoyl chloride, followed by hydrolysis of the resultant ethyl 5-(p-toluoyl)-1-methylpyrrole-2-acetate (6).

• Proceedings of the Korean Society of Applied Pharmacology
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• 2000.04a
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• pp.10-14
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• 2000

The cycloooxygenase enzymes catalyze the oxidative conversion of arachidonic acid into prostag1andin H$_2$Which mediates both benificial and pathological effects. The COX-1 is constitutively expressed in most tissues and in blood platelets wherease the expression of COX-2 isoform is induced in response to inflmmatory stimuli such as cyctokynes. Thus the identification of a novel COX-2 selective inhibitor should offer excellent antiinflammatory activity with minimal side effects such as gastrointestinal toxicity. Recently, a group of structurally unique and biologically active pimarane diterpenoids has been isolated from indigenous Korean medicinal plants. These new diterpenoids turned out to be potential analgesic and antiinflammatory agent due to their potent inhibitory activities of prostaglandin synthesis. We have also found that the inhibition of PGE$_2$synthesis is attributed to the potent COX inhibition by pimarane diterpenoid in arachidonic acid cascade. In conjunction with development of new analgesic and nonsteroidal antiinflammatory agent, a series of works on these diterpenoids have been extensively carried out in our laboratories. These efforts involve the structure-activity relationship of pimaradienoic acid, molecular modelings and COX inibitory activities as well as actiinflammatory effects of its structural analogues. In addition, the total syntheses of the new natural pimarane diterpenoids, their stereoisomers and other structural variants were intensively investigated.

• Journal of Pharmaceutical Investigation
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• v.22 no.1
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• pp.57-63
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• 1992

• YAKHAK HOEJI
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• v.35 no.2
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• pp.119-122
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• 1991

A convenient method for the synthesis of ibuproxam, which is a non steroidal antiinflammatory agent, is reported. Friedel-Crafts reaction of isobutylbenzene with ethyl $\alpha$-chloro-$\alpha$-(methylthio)acetate (3) gives ethyl $\alpha$-methylthio-(p-isobutylpheny) acetate (4). Ethyl 2-methylthio-2-(4-isobutylphenyl) propionate (5) is obtained from methylation of the compound (4) with NaH and Mel. lbuproxam (7) is easily synthesized by reductive desulfurization of the compound (5) with zinc dust-acetic acid or Raney nickel, followed by treatment of the resultant ethyl 2-(4-isobutyl-pheny) propionate (6) with H$_{2}$NOH-HCI.

• Journal of Ginseng Research
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• v.44 no.1
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• pp.145-153
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• 2020

Background: Panax ginseng Meyer (Araliaceae) is a highly valued medicinal plant in Asian regions, especially in Korea, China, and Japan. Chemical and biological studies on P. ginseng have focused primarily on its roots, whereas the seeds remain poorly understood. This study explores the phytochemical and biological properties of compounds from P. ginseng seeds. Methods: P. ginseng seeds were extracted with methanol, and 16 compounds were isolated using various chromatographic methods. The chemical structures of the isolates were determined by spectroscopic data. Antiinflammatory activities were evaluated for triterpene and steroidal saponins using lipopolysaccharide-stimulated RAW264.7 macrophages and THP-1 monocyte leukemia cells. Results: Phytochemical investigation of P. ginseng seeds led to the isolation of a novel triterpene saponin, pseudoginsenoside RT₈, along with 15 known compounds. Pseudoginsenoside RT₈ exhibited more potent antiinflammatory activity than the other saponins, attenuating lipopolysaccharide-mediated induction of proinflammatory genes such as interleukin-1β, interleukin-6, inducible nitric oxide synthase, cyclooxygenase-2, and matrix metalloproteinase-9, and suppressed reactive oxygen species and nitric oxide generation in a dose-dependent manner. Conclusion: These findings indicate that pseudoginsenoside RT₈ has a pharmaceutical potential as an antiinflammatory agent and that P. ginseng seeds are a good natural source for discovering novel bioactive molecules.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1996.11a
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• pp.147-152
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• 1996

In order to discover new useful antiinflammatory agent, many new compounds are continually being synthesized and tested. A certain peptide which contains an anisolated glutamic acid has been reported to show considerable biological activities.