• Bulletin of the Korean Chemical Society
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• v.24 no.8
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• pp.1181-1187
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• 2003

Condensation of 4-cyano-5,6-dimethyl-3-pyridazinone 1 with aromatic aldehydes gave the novel styryl derivatives 2a-c. Refluxing of compound 2a with phosphorus oxychloride furnished 3-chloropyridazine derivative 3. Compound 3 was reacted with thiourea and produced pyridazine-3(2H)thione 4. Thieno[2,3-c]- pyridazines 5a-e were achieved by cycloalkylation of compound 4 with halocompounds in methanol under reflux and in the presence of sodium methoxide. Also, refluxing of compound 4 with N-substituted chloroacetamide in the presence of potassium carbonate afforded thienopyridazines 6a-e. Cyclization of compound 6 with some electrophilic reagents as carbon disulfide and triethyl orthoformate furnished the novel pyrimido[4',5':4,5]thieno[2,3-c]pyridazines 12 and 13a-c, respectively. Diazotisation of compound 6 with sodium nitrite in acetic acid produced the pyridazino[4',3':4,5]thieno[3,2-d][1,2,3]triazines 14a-c. Ternary condensation of compound 1, aromatic aldehydes and malononitrile in ethanol containing piperidine under reflux afforded the novel phthalazines 16a-c. Compound 3 was subjected to some nucleophilic substitution reactions with amines and sodium azide and formed the aminopyridazines 17a, b and tetrazolo[1,5-b]-pyridazine 19, respectively. The structures of the synthesized compounds were established by elemental and spectral analyses.

• Archives of Pharmacal Research
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• v.15 no.1
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• pp.52-57
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• 1992

The molecular structure of a natural compound was determined by single crystal X-ray diffraction analysis. The compound was isolated by methanol extraction and repeated chromatography from the stem of Paulownia tomentosa. Yellow prismatic crystals of the compound, which were recrystallized from tetrahydrofuran, are triclinic, with a = 7.310 (6), b = 10.753(6), c = 11.586(5) ${\AA}.\;\alpha= 93.30(6),\;\beta=105.62(10),\;\gamma=109.49(7)^\circ,\;D_x=1.514,\;D_m=1.51 g/cm^3$, space group P1 and Z = 2. The structure was solved by direct method, and refined by least-squares procedure to the final R-value of 0.032 for 1271 independent reflections $(F\le3\sigma{(F))}$. The compound is one of new furanquinone analogue. The molecule has a nearly planar conformation with an intramolecular hydrogen bond. In the crystal, the planar molecules are arranged as a prallel sheet-like pattern, and these stackings are stabilized by the O-H...O type intermolecular hydrogen bonds. The other intermolecular contacts appear to be the normal van der Waals interactions.

• Natural Product Sciences
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• v.21 no.4
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• pp.278-281
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• 2015

Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-^1H-indol-3-yl) oxoacetamide, respectively, based on $^1H$ and $^{13}C$ NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the anti-inflammatory potential of compound 1.

• The Korean Journal of Physiology and Pharmacology
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• v.17 no.3
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• pp.217-222
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• 2013

We reported that ailanthoidol, a neolignan from Zanthoxylum ailanthoides and Salvia miltiorrhiza Bunge, inhibited inflammatory reactions by macrophages and protected mice from endotoxin shock. We examined the anti-inflammatory activity of six synthetic ailanthoidol derivatives (compounds 1-6). Among them, compound 4, 2-(4-hydroxyphenyl)-5-(3-hydroxypropenyl)-7-methoxybenzofuran, had the lowest $IC_{50}$ value concerning nitric oxide (NO) release from lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Compound 4 suppressed the generation of prostaglandin (PG) $E_2$ and the expression of inducible NO synthase and cyclooxygenase (COX)-2 induced by LPS, and inhibited the release of LPS-induced pro-inflammatory cytokines from RAW264.7 cells. The underlying mechanism of compound 4 on anti-inflammatory action was correlated with the down-regulation of mitogen-activated protein kinase and activator protein-1 activation. Compound 4 is potentially an effective functional chemical candidate for the prevention of inflammatory diseases.

• Bulletin of the Korean Chemical Society
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• v.35 no.4
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• pp.989-993
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• 2014

The molecular structures of 2,6-diaza-1,3,5,7-tetraoxaspiro[3,3]heptane (1) and its dinitro derivative, 2,6-dinitro-2,6-diaza-1,3,5,7-tetraoxaspiro[3,3]heptane (2), were fully optimized without symmetry constraints at $HF/6-31G^*$ level of theory. A bisected conformation with respect to the ring is preferred with a $C_2$ symmetric structure. The density of each molecule in the crystalline state was estimated to 1.12 and 2.36 $g/cm^3$ using PM3/VSTO-3G calculations from the molecular volume. The heat of formation was calculated for two compounds at the CBS-4M level of theory. The detonation parameters were computed using the EXPLO5 software: D = 6282 m/s, $P_{C-J}$ = 127 kbar for compound 1, D = 7871 m/s, $P_{C-J}$ = 307 kbar for compound 2, and D = 6975 m/s, $P_{C-J}$ = 170 kbar for 60% compound 2 with 40% TNT. Specific impulse of compound 1 in aluminized formulation when used as monopropellants was very similar to that of the conventional ammonium perchlorate in the same formulation of aluminum.

• Bulletin of the Korean Chemical Society
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• v.31 no.12
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• pp.3553-3560
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• 2010

A new hydrazone derivative compound has been synthesized and characterized by IR, $^1H$-NMR, $^{13}C$-NMR and UV-vis. spectroscopy techniques, elemental analysis and single-crystal X-ray diffraction (XRD). The new compound crystallizes in monoclinic space group C2/c. In addition to the crystal structure from X-ray experiment, the molecular geometry, vibrational frequencies and frontier molecular orbitals analysis of the title compound in the ground state have been calculated by using the HF/6-31G(d, p), B3LYP/6-311G(d, p) and B3LYP/6-31G(d, p) methods. The computed vibrational frequencies are used to determine the types of molecular motions associated with each of the observed experimental bands. To determine conformational flexibility, molecular energy profile of (1) was obtained by semi-empirical (AM1) calculation with respect to a selected degree of torsional freedom, which was varied from $-180^{\circ}$ to $+180^{\circ}$ in steps of $10^{\circ}$. Molecular electrostatic potential of the compound was also performed by the theoretical method.

• Natural Product Sciences
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• v.5 no.2
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• pp.93-96
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• 1999

A new ergosteryl myristate (1) and ergosterol (2) have been isolated from the organic extract of the mycelium of unidentified marine algicolous fungus, isolate MF001. The structure of a new compound was assigned on the basis of comprehensive spectroscopic analyses and chemical synthesis.

• Natural Product Sciences
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• v.24 no.3
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• pp.155-158
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• 2018

A new flavonol derivative, meliglabrin (1) along with three known flavonols, ternatin (2), meliternatin (3), and 5,4'-dihydroxy-3,7,3'-trimethoxyflavon (4) were isolated from the leaves of Melicope glabra (Blume) T.G. Hartley. Their structures were determined using extensive spectroscopic methods, including UV, IR, HRESIMS, 1D and 2D NMR. Compounds 1 - 4 were evaluated for their cytotoxicity against murine leukemia P-388 cells, compound 4 showed moderate activity.

• YAKHAK HOEJI
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• v.42 no.3
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• pp.257-264
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• 1998

5-Methylthebaine was obtained by treating thebaine with n-butyllithium and methylfluorosulfonate. Hetero Diels-Alder reaction of thebaine and 5-methylthebaine with trifluoroacet aldehyde afforded 14-${\beta}$-(triflu-oro-2-hydroxyethyl)codeine (2) and 14-${\beta}$-(trifluoro-2-hydroxyethyl)-5-methylcodeinone (9). 6-${\alpha}$-OH compound (4) was obtained by employing $CeCl_2$ and $NaBH_4$. After synthesized a derivative substituted for 3-OH (5), using boron tribromied, We synthesized a new derivative that make double bond in C-7, C-8 into epoxode (6), (10). Through inspecting an influence on structure-activity and analgetic action, we are going to examine which opiold acceptor has a selectivity.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1994.04a
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• pp.272-272
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• 1994

신약개발에 있어서 대사연구는 약효의 species difference, 독성기전, 그리고 in vitro와 in vivo의 약효차이를 이해하는데 매우 중요한 역할을 담당하며 그 연구 영역을 넓혀가고 있다. 본 연구에서는 항혈전제로 개발 가능성이 있는 phosphodiesterase inhibitor인 KR30289의 rat과 rabbit에서 대사 연구를 통하여 약리효과의 상이점을 밝히고져 하였다. Mass analysis를 통하여 urinary 대사체의 구조를 규명한 결과 KR30289를 경구 투여 (1mg/kg)시 hydroxy derivative(M1)와 O-dealkylated derivative(M2)로 변환되어 urine으로 배설되었고 parent compound는 검출되지 않았다 M1과 M2 모두 free form, glucuronide conjugate, 그리고 sulfate conjugate 형태로 검출되었으나 rat과 rabbit 두 종간의 M1과 M2의 비율에서는 커다란 차이점을 보여주었다 rat의 경우 M2가 94% (free form : 14%, glucuronide conjugate 58%. sulfate conjugate, 22%)이었으며 rabbit에서는 M1이 54%로 상대적으로 많이 생성되었다(free form : 11%, glucuronide conjugate : 22%, sulfate conjugate 21%). 이와같이 두종간의 상이한 metabolic profile로 인하여 약리효과의 차이가 유발될수 있다고 추론된다.