• Bulletin of the Korean Chemical Society
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• v.26 no.6
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• pp.952-958
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• 2005

Angiotensin-converting enzyme (ACE) is known to be primarily responsible for hypertension. Threedimensional quantitative structure-activity relationship (3D-QSAR) models have been constructed using the comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) for a series of 28 ACE inhibitors. The availability of ACE crystal structure (1UZF) provided the plausible biological orientation of inhibitors to ACE active site (C-domain). Alignment for CoMFA obtained by docking ligands to 1UZF protein using FlexX program showed better statistical model as compared to superposition of corresponding atoms. The statistical parameters indicate reasonable models for both CoMFA ($q^2$ = 0.530, $r^2$ = 0.998) and CoMSIA ($q^2$ = 0.518, $r^2$ = 0.990). The 3D-QSAR analyses provide valuable information for the design of ACE inhibitors with potent activity towards C-domain of ACE. The group substitutions involving the phenyl ring and carbon chain at the propionyl and sulfonyl moieties of captopril are essential for better activity against ACE.

• Archives of Pharmacal Research
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• v.22 no.6
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• pp.565-570
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• 1999

DW2282,(S)-(+)-4-phenyl-1-[1-(4-aminobenzoyl)-indoline-5-sulfonyl]-4,5-dihydro-2-imidazolone hydrochloride, is a new anticancer agent which is thought to exhibit a characteristic mechanism of action in the inhibition of tumor growth. In this study, we estimated the toxicities of DW2282 in mice. When mice were orally dosed for five consecutive days at the dosages of 50, 100 and 150 mg/kg, DW2282 did not induced methemoglobinemia and hypoglycemia at any of these doses. However, increased ALT and AST values were observed in the 150 mg/kg dosing group, and white blood cells (WBC) were significantly decreased at all doses. However, the changes in WBC count, ALT and AST immediately reversed after the cessation of drug administration. In addition, we found that DW2282 did not cause an increase in hemolysis in human blood. Taken together, these data suggested that DW2282 may have a relatively low level of toxicity, and that there may be a quick recovery from any toxicity it dose produce.

• Bulletin of the Korean Chemical Society
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• v.18 no.9
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• pp.939-945
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• 1997

Several types of 4-substituted-quinoline-2-carboxylic acid derivatives possessing different substituents at C4-position such as sulfonyl, phosphonyl, carbonyl groups, or a flexible alkyl chain have been synthesized and evaluated for their in vitro antagonistic activity at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Of them, 5,7-dichloro-4-(tolylsulfonylamino)-quinoline-2-carboxylic acid 9 was found to have the best in vitro binding affinity with IC50 of 0.57 μM. On the other hand, in compounds 21 and 22 the introduction of flexible alkyl chains on C4 of the quinoline mother nuclei caused a significant decrease of the in vitro binding affinity. In addition, replacement of polar carboxylic acid group on C2 by neutral bioisosteres in compounds 23a-d also seems to be disadvantageous to in vitro activity. In the structure-activity relationship (SAR) study of the 4-substituted quinoline-2-carboxylic acid acid derivatives, it was realized that the substitution pattern on C4 significantly influences on the binding affinity for the glycine site of NMDA receptor and the binding affinity might be increased by the introduction of a suitable electron rich substituent at C4 which has the ability of H-bonding donor.

• Journal of the Korean Chemical Society
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• v.18 no.2
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• pp.97-109
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• 1974

The crystal and molecular structure of sulfaguanidine monohydrate, $C_7H_{10}N_4O_2S{\cdot}H_2O$, was determined from visually estimated intensity data from Weissenberg photographs. The crystal data are monoclinic, space group $P2_1$/c with four molecules in a unit cell of dimensions, ${\alpha}=7.57{\pm}0.03,\;b=5.44{\pm}0.02,\;c=24.76{\pm}0.06{\AA},\;{\beta}=91.0{\pm}0.2^{\circ}$. The structure has been solved by an interpretation of a Patterson map and with a help of a direct procedure on a projection. The parameters were refined isotropically by block-diagonal least-squares methods using 1542 observed independent reflections to give R = 0.14. By hydrogen bonding a guanidyl nitrogen of a sulfaguanidine molecule is linked to the sulfonyl oxygens of the other molecules indirectly through two different water molecules. The role of water molecule is both a donor and an acceptor in hydrogen-bonding formation and these hydrogen bonds are tetrahedrally oriented. The hydrogen-bonding networks form infinite molecular layers parallel to (001) plane.

• Analytical Science and Technology
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• v.22 no.4
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• pp.345-353
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• 2009

The new anti-impotency analogue was identified in food source. Detection of this analogue was accomplished through screening of food samples by liquid chromatography/photodiode array detector. The spectrum pattern of analogue compound was similar to that observed for hongdenafil which was analogue of sildenafil. This new compound was isolated and purified using the liquid-liquid extraction, thin layer chromatography, column chromatography and preparative HPLC. And then those structure were identified using analytical instruments such as HPLC/PDA, LC/MS/MS and NMR. The compound was given a name to oxohongdenafil which was replaced with acetyl oxoethylpiperazinyl residue instead of sulfonyl piperazine group of sildenafil. The regulation for the abovementioned analogue, oxohongdenafil, was established by Standard of Korean food code.

• Journal of Integrative Natural Science
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• v.7 no.2
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• pp.92-102
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• 2014

The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a = 28.633(3) ${\AA}$, b= 9.3215(7) ${\AA}$ and c= 24.590(2) ${\AA}$ [alpha & gamma=$90^{\circ}$ beta= $115.976(3)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [119.74 $(2)^{\circ}$] and N1-S1-C5 [$105.57(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($316.2(1)^{\circ}$) indicates that N1 is in sp2 hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. The carboxylate group of atoms were disordered over two positions with site occupancy factors 0.598 (9):0.402 (9). Crystal structure and packing is stabilized by $C-H{\ldots}O$ intra and inter molecular hydrogen bond interactions.

• Applied Biological Chemistry
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• v.39 no.4
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• pp.297-303
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• 1996

A series of the herbicidal N-(4,6-disubstituted pyrimidin-2-yl)aminocarbonyl-2-(1,1-ethylenedioxy-2-fluoro)ethyIbenzenesulfonamides, 1 and N-(4,6-disubstituted triazin-2-yl)aminocarbonyl-2-(1,1-ethylenodioxy-2-flu ore)ethylbenzenosuIfonamides, 2 were synthesized and their herbicidal activities in-vivo against rice(Oryza sativa L.), barnyard grass (Echinochloa crus-galli), bulrush(Scripus juncoides) and pickerel weed(Monochoria vaginalis presl.) were measured by the pot test under the paddy conditions. The structure activity relationships(SAR) between the herbicidal activity$(pI_{50})$ and a various physicochemical parameters of the hetero group and 4,6-disubstituents on the heterocyclic group were analyzed by the multiple regression technique. The SAR suggest that the 4,6-dimethoxypyrimidine substituent, 1a showed selective$({\Delta}obs.pI_{50}=1.12)$ and the most highest activity against barnyard grass, which depend on the hydrophobicity(log P<0) of heterocyclo group and molecular refractivity$((M_R)_{opt.}=14.58cm^3/mol)$ constant of 4,6-disubstituents on the heterocyclic group.

• Korean Chemical Engineering Research
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• v.51 no.2
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• pp.189-194
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• 2013

A sulfonated activated carbon (AC-$SO_3H$) was used as a solid acid catalyst for dehydration of sorbitol to isosorbide and its catalytic performance was compared with the commercial solid acid such as acidic ion exchange resin, Amberlyst-36, and sulfated copper oxide. The catalytic performance with 100% sorbitol conversion and 52% isosorbide selectivity was obtained over AC-$SO_3H$ at 423.15 K. Although AC-$SO_3H$ possessed only 0.5 mmol/g of sulfur content, it showed the similar dehydration activity of sorbitol to isosorbide with Amberlyst-36 (5.4 mmol/g) at 423.15 K. Based on the high thermal and chemical stability of AC-$SO_3H$, one-step reactive distillation, where isosorbide separation can be carried out simultaneously with sorbitol dehydration, was tried to increase the recovery yield of isosobide from sorbitol. The reactive distillation process using AC-$SO_3H$, the turnover number of AC-$SO_3H$ was 4 times higher than the conventional two-step process using sulfuric acid.

• Applied Biological Chemistry
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• v.39 no.3
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• pp.235-240
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• 1996

The most stable stereo conformer in non substituted benzenesulfonyl urea, 1 was the II-keto form, which the molecule was intramolecular associated(H-bond) coformer between imide group and N atom on the Pyrimidine ring. The hydrolytic degradation of 2 derivatives were proceeds by nucleophilic addition reaction(p<0) with orbital controlled intermolecular interaction between LUMO with electron donating$(\sigma<0)$ groups of 2 and HOMO of water molecule. N-(4,6-disub. pyrimid ine-2-yl)aminocarbonyl-2-(1,1-dimethoxy-2-fluoro)ethylbenze nesulfonamides,3 and N-(4,6-disub. triazine-2-yl)aminocarbonyl-2-(1,1-d imethoxy-2-fluoro)ethylbenzenesulfonamides,4 we re synthesized and their herbicidal activities in vivo against bulrush (Scirpus juncoides.) were measured by the pot test under the paddy conditions And the structure activity relationships(SAR) were analyzed by the multiple regression technique. The results of the SAR suggested that the 3 and 4 derivatives indicated dependent on the hydrophobicity of the 4,6-disubstituents and the heterocyclo group, where the optimal value $((log\;P)_{opt.}=0.89)$ of hydrophobicity was 0.89. The pyrimidine substituents, 3 showed higher herbicidal activity than the triazine substituents, 4. Among them, 4,6-dimethoxypyrimidine substituent, 3a showed the best herbicidal activity.

• Journal of Integrative Natural Science
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• v.7 no.3
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• pp.149-158
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• 2014

The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=$8.5775(4){{\AA}$, b=$24.9943(13){\AA}$ and c=$13.7319(7){\AA}$ [alpha & gamma=$90^{\circ}$ beta=$103.558(2)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [$121.08(1)^{\circ}$] and N1-S1-C5 [$105.85(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($354.9^{\circ}$) indicates that N1 is in $sp^2$ hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. Crystal structure is stabilized by C-H...O intra molecular hydrogen bond interactions.