Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 50, Issue 12
Displaying 1-25 of 25 articles from this issue
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Reviews
  • Cross-Coupling Reactions of Organosilicon Compounds: New Concepts and Recent Advances
    Scott Eric Denmark, Ramzi Farah Sweis
    Article type: Review
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1531-1541
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1531
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    This review highlights the rapid evolution of the newly-developed class of palladium-catalyzed cross-coupling reactions of organosilicon compounds. A myriad of heteroatom-containing silicon moieties (silyl hydrides, siletanes, silanols, silyl ethers, orthosiliconates, di- and polysiloxanes and pyridylsilanes) undergo mild and stereospecific cross-coupling. The diversity of methods for introduction of silicon groups into organic molecules and the range of organic electrophiles that can be used are emphasized.
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Regular Articles
  • Preparation of Antipyretic Analgesic by Direct Compression and Its Evaluation
    Keijiro Terashita, Keisuke Imamura
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1542-1549
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1542
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    Direct compression is able to produce tablets at a lower cost than wet granulation and tableting method, due to a fewer items of process validation. In this study, acetaminophen was used as a medicine with various granular diameters to formulate tablets by direct compression, thus evaluating their physical properties. Consequently, direct compression was found effective in formulating tablets with excellent physical properties, with the granular diameter taken into account. It was confirmed that tablets produced by direct compression were similar in physical properties in tablets produced by wet granulation and tableting method. Further, it was suggested that use of a dry-type binder would make it possible to provide a tablet having higher content of the medicine with excellent physical properties.
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  • Optimization of Operating Conditions in a High-Shear Mixer Using DEM Model: Determination of Optimal Fill Level
    Keijiro Terashita, Takehiko Nishimura, Susumu Natsuyama
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1550-1557
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1550
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    For the purpose of evaluating optimal fill level of starting materials in a high-shear mixer, discrete element method (DEM) simulation was conducted to visualize kinetic status between particles. The simulation results obtained by changing fill levels were used to determine solid fraction of particles, particle velocity, particle velocity vector, and kinetic energy and discuss the flow pattern. Optimal fill level was obtained from the information on these matters. It was pointed out that understanding the kinetic energy between particles in an agitating vessel was effective in determining the optimal fill level. Granulation experiment was conducted to validate the optimal fill level obtained by the simulation, confirming the good agreement between these two results. It was pointed out that determination of kinetic energy between particles through the simulation was effective in obtaining an index of the kinetic status of particles. Further, it was confirmed that the simulation could provide more information than conventional granulation experiments could provide and also helpful in optimizing the operating conditions.
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  • Novel Sphingolipids from Conyza canadensis
    Naveen Mukhtar, Kiran Iqbal, Abdul Malik
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1558-1560
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1558
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    New sphingolipids, 1,3,5-trihydroxy-2-hexadecanoylamino-(6E,9E)-heptacosdiene (1), 1,3,5-trihydroxy-2-hexadecanoylamino-(6E,9E)-heptacosdiene-1-O-glucopyranoside (2), 1,3-dihydroxy-2-hexanoylamino-(4E)-heptadecene (3) have been isolated from Conyza canadensis, along with five known compounds, p-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 3,5-dimethoxybenzoic acid, 3β-hydroxyolean-12-en-28-oic acid, and 3β-erythrodiol, isolated for the first time from this species. Their structures were determined by spectroscopic methods (1H- and 13C-NMR, IR and MS) and two dimensional (2D)-NMR experiments.
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  • Taxumairols X—Z, New Taxoids from Taiwanese Taxus mairei
    Ya-Ching Shen, Yao-To Chang, Shih-Sheng Wang, Yu-Chi Lin, Ching-Yeu Ch ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1561-1565
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1561
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    In addition to 19-dydroxybaccatin III, 1β-hydroxy-5α-deacetylbaccatin I, taxayuntin G and 13-O-deacetyltaxumairol Z (4), three new taxane diterpenoids, taxumairols X (1), Y (2), Z (3) have been isolated from extracts of the Formosan Taxus mairei (LEMEE & LEVL.) S. Y. HU. Compounds 1—2 belong to the 11(15→1)-abeo-taxane system, having a tetrahydrofuran ring at C-2, C-3, C-4 and C-20. The new compound 3 and 4, which was misidentified previously are derivatives of 11(15→1)-abeo-taxane with an intact oxirane system. The structures of compounds 1—4 were elucidated on the basis of extensive two dimensional (2D)-NMR analysis.
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  • Anti-allergic Agents from Natural Sources (4): Anti-allergic Activity of New Phloroglucinol Derivatives from Mallotus philippensis (Euphorbiaceae)
    Akihiro Daikonya, Shigeki Katsuki, Jin-Bin Wu, Susumu Kitanaka
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1566-1569
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1566
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    Two new phloroglucinol derivatives, mallotophilippen A (1) and B (2) were isolated from the fruits of Mallotus philippensis. These compounds were identified, using chemical and spectral data, as 1-[5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-isobutyryl-5-methyl-benzyl)-2H-chromen-8-yl]-2-methyl-butan-1-one and 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-2-methyl-butan-1-one, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ). Furthermore, they inhibited histamine release from rat peritoneal mast cells induced by Compound 48/80. These results suggest that the novel phloroglucinol derivatives have anti-inflammatory effects.
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  • Physicochemical Analyses of Phase Transition and Dehydration Processes of a New Oral 1β-Methylcarbapenem Antibiotic Agent, CS-834
    Katsuhiro Kobayashi, Hiroshi Fukuhara, Isao Kawamoto, Tadashi Hata, Ak ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1570-1573
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1570
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    The characterizations of the anhydrate (A-form), monohydrate (B1-form), and dihydrate (B2-form) of CS-834 were investigated by powder X-ray diffraction, differential scanning calorimetry (DSC), thermogravimetry-differential thermal analysis (TG-DTA), infrared spectroscopy, and Karl Fischer moisture titration. The typical DSC curve of the B2-form showed five endothermic peaks at 35.0, 46.4, 56.2, 99.2, and 190.4°C and an exothermic peak at 123.4°C. In TG-DTA analysis, the three peaks at 35.0, 46.4, and 56.2°C had a total weight loss of 7.3%, corresponding to the release of two water molecules. From morphological observation under thermomicroscopy, the endothermic peak at 99.2°C was attributed to the melting of the dehydrous crystals (B0-form) and the exothermic peak at 123.4°C to the recrystallization to the A-form crystals. The endothermic peak at 190.4°C was due to the melting of the A-form crystals. After incubation for 6.0 h at 35, 50, 60, and 80°C, the powder X-ray diffraction patterns of the B2-form indicated that it was converted into the A-form via the B1-form and B0-form. Thus CS-834 exists in homologous hydrous crystal forms in multiple-phase transformations with the dehydration of two water molecules.
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  • Pyridazines. Part 31: Synthesis and Antiplatelet Activity of 4,5-Disubstituted-6-phenyl-3(2H)-pyridazinones
    Eddy Sotelo, Nuria Fraiz, Matilde Yáñez, Reyes Laguna, E ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1574-1577
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1574
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    This paper describes the synthesis and the antiplatelet activity of a series of 4,5-disubstituted-6-phenyl-3(2H)-pyridazinones. Some of these compounds show a dose-dependent activity and were found to be more active than their 5-substituted analogues.
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  • Hydrophobicity Parameters Determined by Reversed-Phase Liquid Chromatography. XV: Optimal Conditions for Prediction of log Poct by Using RP-HPLC Procedures
    Chisako Yamagami, Kaname Kawase, Kyoko Iwaki
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1578-1583
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1578
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    The use of log k derived from reversed phase (RP)-HPLC retention times provides a convenient method for estimating log Poct values (Poct: 1-octanol/water partition coefficient). In order to establish optimal HPLC conditions, the difference between chromatographic (C18 modified column and aqueous methanol eluents) and bulk solvent systems was examined by use of a batch-like equilibration with octane/aqueous methanol. Comparison of values for log PO/M–W (log P for the Octane/MeOH–Water partitioning system) and log k measured for monosubstituted pyrazines at different methanol concentrations, showed closest correlation (r, 0.94) with 50% aqueous methanol; and importantly, under these conditions, log k shows even better correlation (r, 0.99) with log Poct. Effects of residual silanols on HPLC retention with C18 stationary phases were examined. The results show that, in the presence of a small quantity of accessible silanols, the use of 50% aqueous methanol (M50) as eluent yields values of log k directly proportional to log Poct in accord with our earlier proposal that use of log kM50 provides a convenient means for rapid estimation and prediction of log Poct.
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  • Reaction of Phosgene with the Tricycle Related to the Minor Base of Phenylalanine Transfer Ribonucleic Acids
    Taisuke Itaya, Tae Kanai
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1584-1588
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1584
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    1-Benzylwye (8) underwent electrophilic substitution at the 7-position in the presence of phosgene and pyridine in tetrahydrofuran (THF) to afford the 1,4-dihydropyridines (11, 10, and 14) together with the carboxylic acid 6 and its methyl ester 2 after short treatment of the reaction mixture with methanol and then with water. When triethylamine was used instead of pyridine, phosgene reacted with triethylamine rather than 8, producing (E)-3-(diethylamino)propenoyl chloride (17) and diethylcarbamoyl chloride (18).
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  • The Effect of Various Substances on the Suppression of the Bitterness of Quinine–Human Gustatory Sensation, Binding, and Taste Sensor Studies
    Tomoko Nakamura, Atsu Tanigake, Yohko Miyanaga, Tazuko Ogawa, Takeshi ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1589-1593
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1589
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    The purpose of this study was to quantify the degree of suppression of the perceived bitterness of quinine by various substances and to examine the mechanism of bitterness suppression. The following compounds were tested for their ability to suppress bitterness: sucrose, a natural sweetener; aspartame, a noncaloric sweetener; sodium chloride (NaCl) as the electrolyte; phosphatidic acid, a commercial bitterness suppression agent; and tannic acid, a component of green tea. These substances were examined in a gustatory sensation test in human volunteers, a binding study, and using an artificial taste sensor. Sucrose, aspartame, and NaCl were effective in suppressing bitterness, although at comparatively high concentrations. An almost 80% inhibition of bitterness (calculated as concentration %) of a 0.1 mM quinine hydrochloride solution required 800 mM of sucrose, 8 mM of aspartame, and 300 mM NaCl. Similar levels of bitterness inhibition by phosphatidic acid and tannic acid (81.7, 61.0%, respectively) were obtained at much lower concentrations (1.0 (w/v)% for phosphatidic acid and 0.05 (w/v)% for tannic acid). The mechanism of the bitterness-depressing effect of phosphatidic acid and tannic acid was investigated in terms of adsorption and masking at the receptor site. With phosphatidic acid, 36.1% of the bitterness-depressing effect was found to be due to adsorption, while 45.6% was due to suppression at the receptor site. In the case of 0.05 (w/v)% tannic acid, the total bitterness-masking effect was 61.0%. The contribution of the adsorption effect was about 27.5% while the residual masking effect at the receptor site was almost 33%. Further addition of tannic acid (0.15 (w/v)%), however, increased the bitterness score of quinine, which probably represents an effect of the astringency of tannic acid itself. Finally, an artificial taste sensor was used to evaluate or predict the bitterness-depressing effect. The sensor output profile was shown to reflect the depressant effect at the receptor site rather well. Therefore, the taste sensor is potentially useful for predicting the effectiveness of bitterness-depressant substances.
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  • Inhibitory Effects of 1,3-Selenazol-4-one Derivatives on Mushroom Tyrosinase
    Mamoru Koketsu, Sang Yoon Choi, Hideharu Ishihara, Beong Ou Lim, Hoche ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1594-1596
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1594
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    This study reports depigmenting potency of 1,3-selenazol-4-one derivatives, which would be based upon the finding of direct inhibition to mushroom tyrosinase. 1,3-Selenazol-4-one derivatives exhibited inhibitory effect on dopa oxidase activity of mushroom tyrosinase. In this study, inhibitory effects of six kinds of 1,3-selenazol-4-one derivatives (A, B, C, D, E and F) on mushroom tyrosinase were investigated. Compounds at a concentration of 500 μM exhibited 33.4—62.1% of inhibition on dopa oxidase activity of mushroom tyrosinase. Their inhibitory effects were higher than that of kojic acid (31.7%), a well known tyrosinase inhibitor. 2-(4-Methylphenyl)-1,3-selenazol-4-one (A) exhibited the strongest inhibitory effect among them dose-dependently and in competitive inhibition manner.
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  • Effect of the Hydrophobic Nature of Triacetyl-β-cyclodextrin on the Complexation with Nicardipine Hydrochloride: Physicochemical and Dissolution Properties of the Kneaded and Spray-dried Complexes
    Catarina Marques Fernandes, Francisco José Baptista Veiga
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 12 Pages 1597-1602
    Published: 2002
    Released on J-STAGE: December 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1597
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    The inclusion ability of triacetyl-β-cyclodextrin (TAβCD), a hydrophobic cyclodextrin (CD) derivative was examined, using nicardipine hydrochloride (NC) as model drug. The binary compounds were prepared in a 1 : 1 molar ratio by the kneading and the spray-drying techniques. In order to confirm the complexation between NC and TAβCD in the solid state, differential scanning calorimetry, X-ray diffractometry, Fourier transformation-infrared spectroscopy and scanning electron microscopy were carried out and the results were compared with the corresponding physical mixture in the same molar ratio. The kneaded product presented only slight modifications on the drug physicochemical and morphological properties, which could mean that no complex formation occurred during this process. In contrast, spray-drying was found to produce inclusion complexes with amorphous nature. In vitro dissolution studies were carried out in simulated gastric (pH 1.2) and intestinal (pH 6.8) fluids, according to the United States Pharmacopoeia (USP) basket method. The NC in vitro release from the kneaded and spray-dried products was markedly retarded in both dissolution media. However, this retarding effect was significantly more evident for the spray-dried compound. It was concluded that the formation of real inclusion complexes could only be achieved by the spray-drying method.
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