Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 54, Issue 12
Displaying 1-24 of 24 articles from this issue
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Regular Articles
  • Stability Indicating Methods for the Determination of Some Fluoroquinolones in the Presence of Their Decarboxylated Degradates
    Maissa Yacoub Salem, Nabawia Mahmoud El-Guindi, Hanaa Karam Mikael, La ...
    2006 Volume 54 Issue 12 Pages 1625-1632
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1625
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    Two stability-indicating methods, namely densitometric TLC and derivative spectrophotometry for the determination of the fluoroquinolone antibacterials lomefloxacin (Lfx), moxifloxacin (Mfx), and sparfloxacin (Sfx) in the presence of their acid degradates are described. Acid degradation was adopted and the main decarboxylated product separated by TLC. Degradation products were identified confirming a previously mentioned degradation scheme. The densitometric method is based on the separation of the intact drug from its acid degradation product on silica gel G plates using different mobile phases and the spots of the intact drugs were scanned at 288, 290, and 292 nm for Lfx, Mfx, and Sfx, respectively. The derivative spectrophotometric method utilizes first derivative D1 UV spectrophotometry with zero crossing points at 295.2 nm for Lfx, 280.4 and 303.4 nm for Mfx, and 280.8 nm for Sfx. Regression analysis of Beer's plots showed good correlation in the concentration ranges 0.2—1.2, 0.1—1.4, and 0.5—2.0 μg/spot for Lfx, Mfx, and Sfx, respectively, in the densitometric method and 2—16 μg/ml for all drugs in the derivative spectrophotometric method. The proposed methods were successfully applied for the determination of the investigated drugs in bulk powder with mean percentage accuracy ranges from 98.93 to 101.25% for the TLC method and from 98.18 to 100.35% for the D1 method. The proposed methods were also applied for the determination of the investigated drugs in their pharmaceutical dosage forms and their validity was assessed using the standard addition technique with mean percentage recovery ranging from 100.25 to 101.70% in the TLC method and from 99.27 to 102.12% in the D1 method. The selectivity of the proposed methods was tested by the analysis of laboratory-prepared mixtures containing different percentages of the studied drugs and their acid degradates. The proposed methods were found selective for the determination of the intact drugs in the presence of up to 90% of their degradates in the TLC method and 70% for Lfx and 90% for Mfx and Sfx in the D1 method.
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  • Stereo Structure-Controlled and Electronic Structure-Controlled Estrogen-Like Chemicals to Design and Develop Non-estrogenic Bisphenol A Analogs Based on Chemical Hardness Concept
    Shigeki Kobayashi, Hidemi Shinohara, Kyoko Tabata, Naoko Yamamoto, Aki ...
    2006 Volume 54 Issue 12 Pages 1633-1638
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1633
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    The aim of this study was to elucidate the structure–activity relationship of bisphenol A (BPA) analogs using absolute hardness (η) and absolute electronegativity (χ) (chemical hardness) and to design a non-estrogen active BPA. To determine the structure–activity relationships of BPA analogs, we investigated MCF-7 cell proliferation stimulated by BPA analogs and an η–χ diagram based on the electronic structure of the BPA analogs. The results show that the actions of the environmental hormones BPA analogs have two chemical properties; (i) ‘stereo structure-controlled’ and (ii) ‘electronic structure-controlled’ estrogen-like chemical activities. Therefore, we designed and synthesized BPA analogs which do not possess these 2 characteristics, ((i) and (ii)), and demonstrate the non-estrogen activity of the analog.
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  • Two New Dioxopiperazine Derivatives, Arestrictins A and B, Isolated from Aspergillus restrictus and Aspergillus penicilloides
    Takeshi Itabashi, Natsuna Matsuishi, Tomoo Hosoe, Norihiro Toyazaki, S ...
    2006 Volume 54 Issue 12 Pages 1639-1641
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1639
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    In the course of searching for bioactive substances, two new dioxopiperazine derivatives, arestrictins A (1) and B (2), were isolated along with the known dioxopiperazine, cristatin A (3), and the known peptide, asperglucide (4), from the organic extract of the xerophilic fungi, Aspergillus restrictus and Aspergillus penicilloides. The absolute structures of 1 and 2, except for the configuration of the secondary alcohol in 1, were established by spectroscopic and chemical investigation. The absolute configuration of cristatin A (3) was also determined.
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  • Spectrophotometric Determination of Fluoxetine by Batch and Flow Injection Methods
    Abbas Afkhami, Tayyebeh Madrakian, Lida Khalafi
    2006 Volume 54 Issue 12 Pages 1642-1646
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1642
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    A rapid, simple, and accurate spectrophotometric method is presented for the determination of fluoxetine by batch and flow injection analysis methods. The method is based on fluoxetine competitive complexation reaction with phenolphthalein–β-cyclodextrin (PHP–β-CD) inclusion complex. The increase in the absorbance of the solution at 554 nm by the addition of fluoxetine was measured. The formation constant for fluoxetin–β-CD was calculated by non-linear least squares fitting. Fluoxetine can be determined in the range 7.0×10−6—2.4×10−4 mol l−1 and 5.0×10−5—1.0×10−2 mol l−1 by batch and flow methods, respectively. The limit of detection and limit of quantification were respectively 4.13×10−6 mol l−1 and 1.38×10−5 mol l−1 for batch and 2.46×10−5 mol l−1 and 8.22×10−5 mol l−1 for flow method. The sampling rate in flow injection analysis method was 80±5 samples h−1. The method was applied to the determination of fluoxetine in pharmaceutical formulations and after addition to human urine samples.
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  • Isolation and Structure of Four New Ceramides from the Starfish Luidia maculata
    Masanori Inagaki, Yuriko Ikeda, Satoshi Kawatake, Kazufumi Nakamura, M ...
    2006 Volume 54 Issue 12 Pages 1647-1649
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1647
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    A new sphingosine-type ceramide LMCer-1-1 (1) and three new phytosphingosine-type ceramides, LMCer-2-1 (2), LMCer-2-6 (3), and LMCer-2-7 (4), were isolated from the anti-hyperglycemic active ceramide molecular species LMCer-1 and LMCer-2, obtained from the less polar fraction of the chloroform–methanol extract of the whole bodies of Luidia maculata. The structures of these ceramides were determined on the basis of chemical and spectroscopic evidence as: (2S,3R,4E,2′R)-2-(2-hydroxyhexadecanoylamino)-16-methyl-4-octadecene-1,3-diol (1), (2S,3S,4R,2′R)-2-(2-hydroxyhexadecanoylamino)-16-methyl-octadecane-1,3,4-triol (2), (2S,3S,4R,2′R)-2-(2-hydroxydocosanoylamino)-hexadecane-1,3,4-triol (3), and (2S,3S,4R,2′R)-2-(2-hydroxydocosanoylamino)-14-methyl-hexadecane-1,3,4-triol (4).
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  • Two New Glycosides from the Soft Coral Sinularia firma
    Rajesh Kumar, Vijai Lakshmi
    2006 Volume 54 Issue 12 Pages 1650-1652
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1650
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    Two new glycosides, named Firmacosides A and B, together with known fatty esters, batyl alcohol, Δ5,20 sterol and sphingosine derivatives have been isolated from the soft coral Sinularia firma TIX-DUR. On the basis of spectroscopic analysis (1H-NMR, 13C-NMR, 1H–1H COSY, HMQC, HMBC and FAB-MS), Firmacoside A was established as hexadecanyl-1-O-α-D-arabinopyranosyloxy (1→4)-α-D-arabinopyranosyloxy (1→4)-α-D-arabinopyranoside (1), and firmacoside B was elucidated as docosanyl-1-O-α-D-arabinopyranosyloxy (1→4)-3-O-acetyl-α-arabinopyranosyloxy (1→4)-α-D-arabinopyranoside (2).
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  • Synthesis of Heterocyclic Compounds via Nucleophilic Aroylation Catalyzed by Imidazolidenyl Carbene
    Yumiko Suzuki, Tomonori Toyota, Akira Miyashita, Masayuki Sato
    2006 Volume 54 Issue 12 Pages 1653-1658
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1653
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    Xanthones and acridones were synthesized from 3,4-difluoronitrobenzene and 2-fluorobenzaldehydes in two or three steps. The key step was nucleophilic aroylation catalyzed by imidazolidenyl carbene. The nucleophilic aroylation of 3,4-difluoronitrobenzene afforded 2,2′-difluoro-4-nitrobenzophenones. The cyclization of the difluorobenzophenones with O-nucleophile and N-nucleophile yielded 3-nitroxanthones and 3-nitroacridones, respectively. Indazole, quinolino[2,3-b]quinoxaline, and thianaphtho[2,3-b]quinoxaline derivatives were also synthesized via nucleophilic aroylation of 2,3-dichloroquinoxaline followed by cyclization with nucleophiles.
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  • Fungal Citridone D Having a Novel Phenylfuropyridine Skeleton
    Takashi Fukuda, Yasunari Sakabe, Hiroshi Tomoda, Satoshi Omura
    2006 Volume 54 Issue 12 Pages 1659-1661
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1659
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    Citridone D was isolated from the culture broth of Penicillium sp. FKI-1938 by solvent extraction, silica gel column chromatography and HPLC. The structure of citridone D was elucidated by spectroscopic analysis including NMR analysis. Citridone D was found to have a novel phenylfuropyridine skeleton different from those of other citridones. Citridone D potentiated miconazole activity against Candida albicans.
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  • Biomimetic Synthesis of (±)-Galanthamine and Asymmetric Synthesis of (−)-Galanthamine Using Remote Asymmetric Induction
    Manabu Node, Sumiaki Kodama, Yoshio Hamashima, Takahiro Katoh, Kiyohar ...
    2006 Volume 54 Issue 12 Pages 1662-1679
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1662
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    (±)-Galanthamine (1) was synthesized in excellent yield by applying PIFA-mediated oxidative phenol coupling of N-(4-hydroxy)phenethyl-N-(3′,4′,5′-trialkoxy)benzyl formamide (15b) as a key step. Because of the symmetrical characteristics of the pyrogallol moiety in the substrate (15b), the phenol coupling resulted in a sole coupling product except for volatile components from the oxidizing agent. On the basis of the successful results of the above strategy, (−)-galanthamine (1) was synthesized by employing a novel remote asymmetric induction, where conformation of the seven-membered ring in the product of the phenol coupling was restricted by forming a fused-chiral imidazolidinone ring with D-phenylalanine on the benzylic C–N bond of the tri-O-alkylated gallyl amino moiety. The conformational restriction and successive debenzylation of the protected hydroxyl groups on the pyrogallol ring caused diastereoselective cyclization to yield a cyclic ether having the desired stereochemistry for the synthesis of (−)-1.
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  • Starting Point to Molecular Design: Efficient Automated 3D Model Builder Key3D
    Miho Yamada Mizutani, Kensuke Nakamura, Tazuko Ichinose, Akiko Itai
    2006 Volume 54 Issue 12 Pages 1680-1685
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1680
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    Obtaining three-dimensional (3D) structures from structural formulae is a crucial process in molecular design. We have developed a new 3D model builder, Key3D, in which the simplified distance geometry technique and structure optimization based on the MMFF force field are combined. In an evaluation study using 598 crystal structures, the high performance and accuracy of Key3D were demonstrated. In the “flexible-fitting” test, which is focused on practical usefulness in the molecular design process, 88% of the Key3D structures acceptably reproduced the reference crystal structures (root-mean-square deviation <0.6 Å) upon rotation of acyclic bonds. These results indicate that Key3D will be very effective in providing starting points for practical molecular design.
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  • Synthesis of 1,4-Diphenylbutadiene Derivatives: Novel Inducer of Tissue-Type Plasminogen Activator (t-PA) in Cultured Bovine Endothelial Cells
    Hiroshi Sai, Tsuyoshi Ogiku, Hiroshi Ohmizu, Akio Ohtani
    2006 Volume 54 Issue 12 Pages 1686-1693
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1686
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    (E,E)-1,4-Diphenylbutadiene derivatives were synthesized by utilizing the Stobbe reaction of dimethyl succinate as a key step. Their stereoisomers were also synthesized stereoselectively by means of the cross-coupling reaction of the vinylstannanes and the vinylbromides, which were obtained from the propiolic acid esters by stereoselective hydrostannation, as a key step. To discover novel stimulators of fibrinolysis in vascular endothelial cells, the synthesized compounds were added to cultured bovine endothelial cells to determine the activity of the plasminogen activator in the conditioned medium. Of the synthesized compounds, three compounds were found to stimulate the activity of the plasminogen activator in endothelial cells. In addtition, these compounds inhibited thrombus formation in a rat model of venous thrombosis.
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  • Antiproliferative Constituents from Umbelliferae Plants. IX. New Triterpenoid Glycosides from the Fruits of Bupleurum rotundifolium
    Toshihiro Fujioka, Keisuke Yoshida, Hiroko Shibao, Tsuneatsu Nagao, Mi ...
    2006 Volume 54 Issue 12 Pages 1694-1704
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1694
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    The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. Bioactivity-guided fractionation of the MeOH extract led to the isolation of four new triglycosides of 13β,28-epoxy oleanane-type triterpenes, named rotundiosides O, Q, S and T; 12 new glycosides of oleanane-type triterpenes, named rotundiosides J—N, P, R, U—Y, and others; echinocystic acid 3-O-sulfate; and three known oleanane-type triterpene glycosides, rotundiosides A, F and G. The structures of the new isolates were determined based on chemical and spectroscopic evidence. The GI50 of isolates against MK-1, HeLa and B16F10 cell lines are reported.
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  • Five New Phenylethanoid Glycosides from the Whole Plants of Lamium purpureum L.
    Nanoko Ito, Tamotsu Nihei, Rie Kakuda, Yasunori Yaoita, Masao Kikuchi
    2006 Volume 54 Issue 12 Pages 1705-1708
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1705
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    Five new phenylethanoid glycosides, lamiusides A (1), B (2), C (3), D (4) and E (5), were isolated from the whole plants of Lamium purpureum L. (Labiatae) together with seven known compounds (6—12). On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 2-(3,4-dihydroxyphenyl)ethyl-O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-(4-O-trans-caffeoyl)-β-D-glucopyranoside (1), 2-(3,4-dihydroxyphenyl)ethyl-O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-(4-O-trans-feruloyl)-β-D-glucopyranoside (2), 2-(3,4-dihydroxyphenyl)ethyl-O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-(6-O-trans-caffeoyl)-β-D-glucopyranoside (3), 2-(3,4-dihydroxyphenyl)-R,S-methoxy-ethyl-O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-(4-O-trans-caffeoyl)-β-D-glucopyranoside (4) and 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1→6)-(4-O-cis-feruloyl)-β-D-glucopyranoside (5). In addition, the radical-scavenging activities of compounds 1—4 on 1,1-diphenyl-2-picrylhydrazyl radical were examined.
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  • Mono- and Dihydroxylated Metabolites of Thalidomide: Synthesis and TNF-α Production-Inhibitory Activity
    Takanori Nakamura, Tomomi Noguchi, Hisayoshi Kobayashi, Hiroyuki Miyac ...
    2006 Volume 54 Issue 12 Pages 1709-1714
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1709
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    Mono- and dihydroxylated metabolites of thalidomide were efficiently prepared and characterized, and their inhibitory activity on tumor necrosis factor (TNF)-α production in the human monocytic leukemia cell line THP-1 was evaluated. 5,N-Dihydroxythalidomide was a much more potent TNF-α production inhibitor than thalidomide.
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  • Chemistry of Unprotected Amino Acids in Aqueous Solution: Direct Bromination of Aromatic Amino Acids with Bromoisocyanuric Acid Sodium Salt under Strong Acidic Condition
    Yuusaku Yokoyama, Tomotsugu Yamaguchi, Masanori Sato, Eri Kobayashi, Y ...
    2006 Volume 54 Issue 12 Pages 1715-1719
    Published: 2006
    Released on J-STAGE: December 01, 2006
    DOIhttps://doi.org/10.1248/cpb.54.1715
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    Brominations of unprotected aromatic amino acids such as phenylalanine, tyrosine, and glycine, with bromoisocyanuric acid mono sodium salt (BICA-Na) were conducted in 60% aq. H2SO4 at 0 °C to give a mixture of mono-brominated products in good yield. Unexpectedly, meta-bromophenylglycine was obtained as main product accompanied by ortho- and para-substituted products, while phenylalanine gave only ortho- and para-substituted products. Bromination of 2-phenylethylamine or benzylamine showed a tendency similar to the corresponding amino acids.
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