Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
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ISSN-L : 0009-2363
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Volume 51, Issue 9
Displaying 1-22 of 22 articles from this issue
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Regular Articles
  • Abnormal Dissolutions of Chlorpromazine Hydrochloride Tablets in Water by Paddle Method under a High Agitation Condition
    Nobuo Aoyagi, Annie Policarpio Rimando, Kenichi Izutsu, Noriko Katori, ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1021-1024
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1021
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    All sugar-coated tablets of chlorpromazine hydrochloride except for those produced by one manufacture showed concave dissolution profiles in water by paddle method at 100 rpm but not at 50 rpm. The study was undertaken to clarify the agitation-dependent abnormal dissolutions. The strange dissolutions were also observed in water at different ionic strengths but not in buffer solutions of pH 1.2, 4.0 and 6.8. When monitored, the pH's of water in dissolution vessels for the abnormal tablets increased with time at 100 rpm and some of them exceeded pH 8 but did not at 50 rpm. The solubility of chlorpromazine hydrochloride decreased with the increase of pH which was too low to dissolve the whole amount of drug contained in a tablet at pH 8. The elevation of pH seemed to be mainly brought about by dissolution of calcium carbonate popularly used for sugar-coated tablets, because larger amount of calcium ion was dissolved out from the abnormal tablets at 100 rpm than from a normal tablet and from them at 50 rpm. These findings indicate that the concave dissolution profiles should be caused by the decrease of drug solubility with increase in pH of water, probably because of dissolution of calcium carbonate. We should pay attention to the change in pH of water which may differ depending on the agitation speed of dissolution tests.
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  • Synthesis of 1-Substituted-6-methyluracils
    Rosa Maria Nieto, Alberto Coelho, Ana Martínez, Angela Stefanac ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1025-1028
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1025
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    A series of 6-methyl-1H-pyrimidin-2,4-diones bearing different substituents in the 1-position of the uracil ring were prepared starting from substituted ureas and diketene.
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  • Formulation Study for Lansoprazole Fast-disintegrating Tablet. II. Effect of Triethyl Citrate on the Quality of the Products
    Toshihiro Shimizu, Norio Kameoka, Hiroshi Iki, Tetsuro Tabata, Naoru H ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1029-1035
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1029
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    The purpose of this study was to develop enteric-coated microgranules for the lansoprazole fast-disintegrating tablet (LFDT), which is a rapidly disintegrating tablet containing enteric-coated microgranules. In our previous study, it was clarified that sufficient flexibility of the enteric layer was achieved by the optimized combined ratio of methacrylic acid copolymer dispersion to ethyl acrylate–methyl methacrylate copolymer dispersion and adding the optimized concentration of triethyl citrate to reduce the damage during the compression process. However, since triethyl citrate has an unpleasant bitter taste and is especially incompatible with lansoprazole, it adversely affects the taste and stability of lansoprazole in the enteric-coated microgranules. The enteric layer containing macrogol 6000 was proven useful to improve the unpleasant bitter taste and stability of lansoprazole, because macrogol 6000 does not have an unpleasant bitter taste and is more compatible than triethyl citerate. By covering the inner (first enteric layer) and outer side (third enteric layer) of the enteric layer containing triethyl citrate (second enteric layer) with the enteric layer containing macrogol 6000, we resolved the stability problem of lansoprazole and the unpleasant bitter taste. Finally, we developed enteric-coated microgranules comprising seven layers: 1) core, 2) active compound layer, 3) intermediate layer, 4) first enteric layer, 5) second enteric layer, 6) third enteric layer, and 7) over coating layer. The enteric-coated microgranules have the multiple functions of reducing the damage to the enteric layer during the compression process, improving the stability of lansoprazole, and masking the unpleasant bitter taste.
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  • Acylated-oxypregnane Glycosides from the Roots of Araujia sericifera
    Tsutomu Warashina, Tadakata Noro
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1036-1045
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1036
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    Twenty-three new acylated-oxypregnane glycosides were obtained from the roots of Araujia sericifera. (Asclepiadaceae). These glycosides were confirmed to be tetraglycosides possessing twelve known compounds, 12-O-benzoyllineolon, 12-O-benzoyldeacylmetaplexigenin, ikemagenin, kidjolanin, cynanchogenin, caudatin, rostratamine, penupogenin, 12-O-benzoylisolineolon, 12-O-tigloyldecylmetaplexigenin (incisagenin), 12-O-benzoyl-20-O-acetylsarcostin, 20-O-benzoyl-12-O-(E)-cinnamoyl-3β,5α,8β,12β,14β,17β,20-heptahydroxy-(20S)-pregn-6-ene and ten new acylated-oxypregnanes, 12-O-benzoyl-20S-hydroxyisolineolon, 12-O-tigloyllineolon, 12-O-salicyloyllineolon, 12-O-salicyloyldeacylmetplexigenin, 12-O-benzoyl-3β,5α,8β,12β,14β,17β-hexahydroxypregn-6-en-20-one, 12-O-benzoyl-19-benzoyloxydeacylmetapleligenin, 12-O-benzoyl-19-benzoyloxy-20-O-acetylsarcostin, 12-O-benzoyl-19-salicyloyloxy-20-O-acetylsarcostin, 12-O-benzoyl-5α,6α-epoxydeacylmetaplexigenin, and 12-O-benzoyl-5α,6α-epoxylineolon as their aglycones, using both spectroscopic and chemical methods.
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  • Is Nitric Oxide (NO) an Antioxidant or a Prooxidant for Lipid Peroxidation?
    Kazuyuki Hiramoto, Takumi Ohkawa, Natsuki Oikawa, Kiyomi Kikugawa
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1046-1050
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1046
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    Antioxidant and prooxidant effects of nitric oxide (NO) on lipid peroxidation in aqueous and non-aqueous media were examined. In an aqueous solution, NO did not induce peroxidation of unoxidized methyl linoleate (ML) and suppressed the radical initiator-induced oxidation of ML. NO suppressed the Fe(II) ion-induced oxidation of mouse liver microsomes. NO reduced the O2 consumption during the radical initiator-induced oxidation of linoleic acid in an aqueous medium. NO conversion into NO2− in an aqueous medium was not affected by unoxidized ML and was slightly reduced by peroxidizing ML. On the other hand, as well as pure NO2, NO induced peroxidation of unoxidized ML in n-hexane in a dose-dependent fashion. NO did not suppress the radical initiator-induced oxidation of ML in n-hexane. Nitrogen oxide species (NO2 or N2O3) formed by autoxidation was dramatically lost in n-hexane in the presence of unoxidized ML. The results indicated that NO terminated lipid peroxidation in an aqueous medium, whereas NO induced lipid peroxidatiton in a non-aqueous medium. Hence, NO showed both antioxidant and prooxidant effects on lipid peroxidation depending on the solvents.
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  • Structures of New Friedelane- and Norfriedelane-Type Triterpenes and Polyacylated Eudesmane-Type Sesquiterpene from Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) and Radical Scavenging Activities of Principal Constituents
    Akinobu Kishi, Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1051-1055
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1051
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    Two new friedelane-type triterpenes, salasones D and E, a new norfriedelane-type triterpene, salaquinone B, and a new polyacylated eudesmane-type sesquiterpene, salasol B, were isolated from the stems of Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. Some norfriedelane-type triterpene, lignan, and catechin constituents were found to show radical scavenging activity.
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  • Thermodynamics of Partitioning of Phenothiazine Drugs between Phosphatidylcholine Bilayer Vesicles and Water Studied by Second-Derivative Spectrophotometry
    Shigehiko Takegami, Keisuke Kitamura, Tatsuya Kitade, Ai Kitagawa, Kik ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1056-1059
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1056
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    The partition coefficients (Kps) of phenothiazine drugs (trifluoperazine, triflupromazine, chlorpromazine and promazine) between phosphatidylcholine (PC) small unilamellar vesicles (SUV) and water were determined over the temperature range of 10—40 °C by a second-derivative spectrophotometric method. The second derivative spectra of each drug solution containing various amounts of SUV showed distinct derivative isosbestic points confirming the entire elimination of the residual background signal effects of the SUV. The Kp values were calculated from the derivative intensity change of the drugs induced by the addition of SUV to the drug buffer solutions (pH 7.4) and obtained with the R.S.D. below 10% (n=3). The van't Hoff analysis of the temperature dependence of Kp values revealed negative ΔHw→l and positive ΔSw→l, suggesting an enthalpy/entropy driven mechanism for the phenothiazine partitioning. The negative ΔHw→l implies that the electrostatic interaction, positively charged alkyl amino groups of phenothiazine drugs with negatively charged phosphate groups on the surface of PC SUV, partly contributes to the partitioning. The existence of halogen atom(s) on the phenothiazine ring at position C-2 enhanced the Kp value (H<Cl<CF3). This enhancement can be accounted for by an increase in the ΔSw→l value (H<Cl<CF3), and the ΔSw→l increase is considered to be enhancement of disorder in the hydrophobic acyl chain regions of PC SUV membranes derived from the phenothiazine ring insertion and thus depends on the bulkiness of the substituent. The enthalpy–entropy correlation analysis yielding a good linear relationship also suggests that the phenothiazine drugs studied have identically an enthalpy–entropy compensation mechanism for the partitioning.
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  • Carbocyclic Analogues of Nucleosides from bis-(Hydroxymethyl)-cyclopentane: Synthesis, Antiviral and Cytostatic Activities of Adenosine, Inosine and Uridine Analogues
    José Manuel Blanco, Olga Caamaño, Franco Fernánde ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1060-1063
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1060
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    Six new carbocyclic nucleosides were prepared by constructing a purine base (in compounds 9—11) or pyrimidine base (in 6—8) on the amino groups of (±)-(1β,2α,4β)-4-amino-1,2-cyclopentanedimethanol (4) and (±)-(1β,3α,4β)-4-amino-1,3-cyclopentanedimethanol (5), and their activities against a variety of viruses and tumour cell lines were determined.
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  • Curtisians M—Q: Five Novel p-Terphenyl Derivatives from the Mushroom Paxillus curtisii
    Dang Ngoc Quang, Toshihiro Hashimoto, Makiko Nukada, Isao Yamamoto, Ma ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1064-1067
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1064
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    Five novel p-terphenyl derivatives called curtisians M—Q (1—5) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii. Their structures were elucidated by two dimensional (2D) NMR, MS, IR, and UV spectroscopy, and chemical reaction. Their antioxidative activities were also investigated.
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  • Pericyclic Reaction of Ketenes with Cascade Reaction Products of Pyridine N-Oxides and Dipolarophiles. X-Ray Structures of the Adducts and Formation Mechanism
    Shigeru Oiso, Masashi Eto, Yasuyuki Yoshitake, Kazunobu Harano
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1068-1074
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1068
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    The structures of the adducts derived from the reactions of substituted ketenes with dihydropyridine derivatives have been clarified by single crystal X-ray analyses and the formation mechanism is discussed on the basis of the reaction-path calculations by semiempirical and density functional theory (DFT) molecular orbital methods.
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  • Preparation of Non-peptide, Highly Potent and Selective Antagonists of Arginine Vasopressin V1A Receptor by Introduction of Alkoxy Groups
    Yoshiaki Shimada, Nobuaki Taniguchi, Akira Matsuhisa, Takeyuki Yatsu, ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1075-1080
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1075
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    A series of compounds structurally related to 4′-[(4,4-difluoro-5-methylidene-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl)carbonyl]benzanilide were synthesized and evaluated for arginine vasopressin (AVP) antagonistic activity. Compounds with alkoxy groups (especially ethoxy group) at the 2′-position of benzanilide possessed potent affinity and selectivity for the V1A receptor versus V2 receptor. Further study has shown that the introduction of 4,4-dimethylaminopiperidino and morpholino groups at carbonylmethylene exhibited more potent affinity and selectivity for V1A receptors. Consequently, we found that the (Z)-4′-({4,4-Difluoro-5-[(4-dimethylaminopiperidino)carbonylmethylene]-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl}carbonyl)-2-ethoxybenzanilide monohydrochloride (8d) and the (Z)-4′-[(4,4-Difluoro-5-morpholinocarbamoylethylene-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl)carbonyl]-2-ethoxybenzanilide (8q) exhibited potent and selective V1A receptor antagonist activity. The synthesis and pharmacological properties of these compounds are detailed in this paper.
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Notes
  • Two New Macrocyclic Diaryl Ether Heptanoids from Boswellia ovalifoliolata
    Vanimireddy Lakshmi Niranjan Reddy, Kodela Ravinder, Masuna Srinivasul ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1081-1084
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1081
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    The stems of Boswellia ovalifoliolata BAL. & HENRY (Burseraceae) afforded two new macrocyclic diaryl ether heptanoids, ovalifoliolatin A (1) and B (2) together with three known compounds; acerogenin C (3), 3α-hydroxyurs-12-ene (4), and sitost-4-en-3-one (5). The structures were established by means of spectroscopic analysis and compounds 1, 3—5 were evaluated for their antibacterial activity.
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  • Depigmenting Activity and Low Cytotoxicity of Alkoxy Benzoates or Alkoxy Cinnamte in Cultured Melanocytes
    Hak Hee Kang, Ho Sik Rho, Jae Sung Hwang, Seong-Geon Oh
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1085-1088
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1085
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    To obtain effective and safe topical depigmenting agents, we synthesized hydroxybenzoates, alkoxybenzoates, and 3,4,5-trimethoxycinnamate containing a thymol moiety and screened then for high-level inhibitory activity against melanin synthesis in cultured melanocytes. Eight compounds were tested for their depigmenting effect and cytotoxicity using a murine melanocyte cell line. We found that 3,4,5-trialkoxybenzoates and 3,4,5-trimethoxycinnamate, synthesized by conjugating 3,4,5-trialkoxybenzoic acids and 3,4,5-trimethoxycinnmic acid with thymol, showed a potent depigmenting effect and low cytotoxicity. Compound 4h, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate, showed the most potent depigmenting effect (IC50=10 μM) with low cytotoxicity (IC50=200 μM).
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  • Two New Pregnane Glycosides from Dioscorea futschauensis R. KUNTH
    Hongwei Liu, Zhili Xiong, Famei Li, Gexia Qu, Hisayoshi Kobayashi, Xin ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1089-1091
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1089
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    Two new pregnane glycosides (1, 2) together with two known saponins were isolated from the rhizomes of Dioscorea futschauensis R. KUNTH. The structures of 1 and 2 were established as 16α-methoxyl-3β-[(O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl)oxy]pregn-5-en-20-one and 21-methoxyl-3β-[(O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl)oxy]pregn-5,16-en-20-one, respectively, on the basis of two-dimension NMR (2D NMR) and other spectral analysis. Their in vitro bioactivity against plant pathogenic fungus Pyricularia oryzae and osteoblastic proliferation stimulatory activity in the UMR106 cell line were evaluated.
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  • Determination of Aromatic and Branched-Chain Amino Acids in Plasma by HPLC with Electrogenerated Ru(bpy)33+ Chemiluminescence Detection
    Kazuo Uchikura
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1092-1094
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1092
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    An HPLC method is described for the electrochemiluminescence (ECL) detection of amino acids, following cycloaddition reaction of their amino groups with divinyl sulfone (DVS), using electrogenerated tris(bipyridine)ruthenium(III). The derivatization reaction conditions were examined, with the optimum conditions found to be 40 mM DVS (pH 8.0) at 50 °C for 15 min. Detection limits for the 15 amino acids examined varied greatly (0.04—8.0 pmol) using a standard solution by flow injection analysis (FIA). These optimized conditions were used for HPLC determination of the amino acids in human plasma. A linear relationship was obtained up to 100 pmol on a column for aromatic and branched-chain amino acids. Recoveries of Tyr, Met, Val, Leu, Ile, Phe and Trp when added to human plasma (1 μmol/10 ml plasma, n=5) were 101.5±1.1, 99.0±1.2, 98.0±1.4, 101.1±1.6, 95.1±1.6, 99.2±1.5 and 97.7±1.3 % (mean±S.D.) respectively. The concentrations of the amino acids in the plasma are in good agreement with other published data.
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  • A Novel Biflavonoid from Roots of Glycyrrhiza uralensis Cultivated in China
    Hong Bai, Wei Li, Kazuo Koike, Deqiang Dou, Yuping Pei, Yingjie Chen, ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1095-1097
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1095
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    A novel biflavonoid named licobichalcone was isolated from the roots of Glycyrrhiza uralensis cultivated in China, along with twelve known compounds, including five chalcones, two isoflavones, two flavanones, two flavones and one pterocarpan. Their structures were respectively elucidated on the basis of chemical and spectroscopic evidence.
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  • Cyclooxygenase Inhibitors Derived from Thalidomide
    Mamiko Suizu, Yohei Muroya, Hiroki Kakuta, Hiroyuki Kagechika, Aya Tan ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1098-1102
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1098
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    Several N-3,5-dimethylphenylphthalimide analogs possessing more potent cyclooxygenase-inhibiting activity than that of aspirin were prepared during structural development studies based on thalidomide. Substituent effects on the activity were investigated.
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  • A New Iridoid Glycoside with Nerve Growth Factor-Potentiating Activity, Gelsemiol 6′-trans-Caffeoyl-1-glucoside, from Verbena littoralis
    Yushan Li, Masami Ishibashi, Masayuki Satake, Yasukatsu Oshima, Yasush ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1103-1105
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1103
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    A new iridoid glycoside, gelsemiol 6′-trans-caffeoyl-1-glucoside (1), was isolated from Verbena littoralis, together with four known phenylethanoid glycosides, acteoside (2), 2′-acetylacteoside (3), jionoside (4), and isoverbascoside (5). Their structures were elucidated by spectral data. Compound 1 showed weak enhancement of nerve growth factor (NGF)-mediated neurite outgrowth from PC12D cells.
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  • Glycosides of Atractylodes ovata
    Junichi Kitajima, Akane Kamoshita, Toru Ishikawa, Akihito Takano, Tats ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1106-1108
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1106
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    A new coumarin glycoside and a new glycoside of an acetylene derivative were isolated from the water-soluble portion of the methanolic extract of Atractylodes ovata rhizome together with eight known compounds. Their structures were characterized as scopoletin β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside and (2E)-2-decene-4,6-diyne-1,8-diol 8-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, respectively, based on chemical and spectroscopic investigations. A comparison of the polar constituents among Atractylodes japonica, Atractylodes lancea, and A. ovata is led to the conclusion that A. ovata is distinguishable from A. lancea and A. japonica, as also shown by phylogenetic analysis.
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  • Synthesis and Evaluation of 6-Nitro-7-(1-piperazino)quinazolines: Dual-Acting Compounds with Inhibitory Activities toward Both Tumor Necrosis Factor-α (TNF-α) Production and T Cell Proliferation
    Masanori Tobe, Yoshiaki Isobe, Hideyuki Tomizawa, Takahiro Nagasaki, M ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1109-1112
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1109
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    We investigated the chemical modifications of the nitroquinazoline derivative (1) through the replacement of the NH group at the C(4)-position with several N-alkyl groups to increase the lipophilicity at the C(4)-position. Among them, we found that the N-methyl analogue (5a) showed a 2-fold loss in the inhibitory activity toward tumor necrosis factor-α (TNF-α) production in vitro as compared with the NH analogue (1); however, 5a exhibited an oral inhibitory activity on TNF-α production with an ED50 value of 26 mg/kg, whereas 1 did not. Moreover, the oral bioavailability of 5a was higher than that of 1 (1, F=1%; 5a, F=21%), and the calculated ClogP value for 5a was higher than that for 1. These results suggest that the improved lipophilicity of 5a compared with that of 1 reflects its greater inhibitory activity on TNF-α production in vivo as well as oral bioavailability.
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  • Synthesis of 1-Triazolyl-4-trimethylsilyl-2-butanol and 1-Triazolyl-5-trimethylsilyl-2-pentanol Derivatives and an Investigation of Their Fungicidal Activities
    Hiroyuki Itoh, Rieko Yoneda, Junzo Tobitsuka, Hiroshi Ohta, Yukiyoshi ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 9 Pages 1113-1116
    Published: 2003
    Released on J-STAGE: September 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1113
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    A new series of azole derivatives of 1-triazolyl-4-trimethylsilyl-2-butanol and 1-triazolyl-5-trimethylsilyl-2-pentanol were synthesized and evaluated for fungicidal activities against rice blast, sheath blight, and powdery mildew on barley. The derivatives of 2,4-difluorobenzene exhibited high antifungal activities when applied by spray, but exhibited no fungicidal activity by submerged application.
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