• Archives of Pharmacal Research
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• v.19 no.2
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• pp.160-162
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• 1996

The structural analysis of tolfenamic acid, 2-[(3-chloro-2-methylphenyl)-amino]benzoic acid, was performed by single crystal X-ray diffraction technique. The compound was recrystallized from a mixture of ether and toluene in triclinic, space group $P2_1/c, \;with\; \partial=3.914(1), \; b=22.\; 020(2), \; c=14.271(1)\;{\AA}, \beta.=94.68(1)^{\circ}, $ and Z=4. The calculated density is $1.418 g/cm^3$. The structure was solved by the direct method and refined by full matrix least-squares procedure to the final R value of 0.039 for 1773 independent reflections. In the molecule, carboxyl group at the anthranilic acid is coplanar to the phenyl ring. The dihedral angle between the two aromatic rings of the molecule is $44.2^{\circ}$ The molecules are dirnerized through the intermolecular hydrogen bonds at the carboxyl group in the crystal.

• YAKHAK HOEJI
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• v.54 no.5
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• pp.387-391
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• 2010

Polygonum cuspidatum which is widely distributed in Korea has been used as treatments of dermatitis, gonorrhea and inflammation in traditional medicine. We examined anti-inflammatory activities by the inhibition of NO production in RAW264.7 murine macrophages cells. Phytochemical examination of Polygonum cuspidatum led to the isolation and characterization of emodin (1), emodin 8-O-${\beta}$-D-glucopyranoside (2), emodin 1-O-${\beta}$-D-glucopyranoside (3). Antioxidative activities of these compounds were determined by measuring the radical scavenging effects on DPPH radicals. Compounds 1 and 3 showed potent activities compared with L-NMMA. These results suggested that the antraquinone compounds isolated from Polygonum cuspidatum might be used as antiinflammatory agents.

• Biomolecules & Therapeutics
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• v.9 no.2
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• pp.69-78
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• 2001

Cyclooxygenase (COX) is an enzyme, which catalyzes the production of prostaglandins from arachi-donic acid and exists in two isoforms (COX-1 and COX-2). COX-1 is involved in the maintenance of physiological functions such as platelet aggregation, cytoprotection in the stomach and maintenance of normal kidney function. COX-2 is induced significantly in vivo under inflammatory conditions. COX-1 and COX-2 serve different physiological and pathological functions. All commercially available nonsteroidal antiinflammatory drugs (NSAIDS) are inhibitors of both COX-1 and COX-2. Therefore, selective inhibitors of COX-2 may be effective antiinflammatory agents without the ulcerogenic effects associated with current NSAms. Since the mid 1990s, a number of reports have been appeared on the preparation and biological activity of selective COX-2 inhibitors. Recently celecoxib, and rofecoxib, the representative COX-2 inhibitors, are introduced in the drug market. In this paper the relationship of structure-activity for selective COX-2 inhibitors is reviewed.

• YAKHAK HOEJI
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• v.38 no.5
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• pp.504-510
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• 1994

A facile synthesis of 2-aryl-5-benzoxazolepropionic acid derivatives(1 0a-d), which are potent antiinflammatory agent, is reported. Methyl ${\alpha}$-(p-hydroxyphenyl)propionate(5) was prepared from Friedel-Crafts reaction of isopropoxy benzene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio) acetate(1), followed by desulfurization, methylation and clevage of ether bond. Compounds(10a-d) were made from(5) by a sequence of nitration, reduction, formation of benzoxazole ring, and hydrolysis in good yields, respectively.

• 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.

• Archives of Pharmacal Research
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• v.8 no.3
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• pp.139-147
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• 1985

Americal A from the seeds of Phytolacca americana, was investigated for the antiinflammatory activity. The compound significantly inhibited edema induction, granuloma formation, arthritis induction and leucocyte emigration in CMC-pouch. But its anticarrageenin activity was not exhibited in adrenalectomized rats. These findings together with decrease in the contents of ascorbic acid and cholesterol in adrenals by administration of the compound suggest that its activity is mediated through stimulation of the pituitary-adrenal axis. The acute toxicity of the compound is very weak and gastric ulceration was not produced by the compound.

• 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).

• Bulletin of the Korean Chemical Society
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• v.6 no.4
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• pp.222-224
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• 1985

The crystal structure of sulindac, $C_{20}H_{17}Fo_3S$, one of the nonsteroid antiinflammatory agents, has been determined by the X-ray diffraction techniques using diffractometer data obtained by the $\varpi-2{\theta}$ scan technique with Cu $$K_{\alpha}$$ radiation from a crystal with space group symmetry Pbca and unit cell parameters a = 8.166(1), b = 18.291(8), c = 23.245(10) ${\AA}.$ The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.11 for the 1153 observed reflections. The carboxyl group is nearly perpendicular to the indenyl ring as observed in indomethacin. The dihedral angle between the indenyl and phenyl rings is $35^{\circ}while$ the corresponding angle in indomethacin is $67^{\circ}.$ Crystal packing consists of a hydrogen bond and partial ring stacking between the indenyl rings.

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