Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 53, Issue 10
Displaying 1-36 of 36 articles from this issue
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Review
  • Development of Useful Reactions Involving Tandem Cyclizations Based on the Novel Reactivities of Allenic Compounds
    Hiroaki Ohno
    2005 Volume 53 Issue 10 Pages 1211-1226
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1211
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    This review highlights author's recent study on allenic compounds. In the first section, organocopper-mediated ring-opening reaction of ethynylaziridines and palladium-catalyzed reductive synthesis of allenes including those which are not accessible by other means, are described. In the second section, palladium-catalyzed stereoselective cyclization of allenes and tandem reaction leading to aziridines, pyrrolidines, benzoisoindoles, and cyclopropanes are presented. The final section presents aziridination and medium-ring formation by intramolecular reaction of bromoallenes, which are scarcely investigated until quite recently. The latter reaction is based on our recent discovery that bromoallenes can act as allylic dication equivalents in the presence of a palladium catalyst and alcohol.
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Regular Articles
  • Application of Multidimensional Scaling to Preformulation Sciences: A Discriminatory Tool to Group Microcrystalline Celluloses
    Celine Valeria Liew, Josephine Lay Peng Soh, Fei Chen, Daming Shi, Pau ...
    2005 Volume 53 Issue 10 Pages 1227-1231
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1227
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    Pre-formulation studies constitute the first step of any pharmaceutical product development and manufacture. Establishment of a comprehensive library of critical physical, chemical, biological and mechanical properties of all materials used for a formulation can be costly, tedious and time consuming, despite its importance in quality manufacturing management. This study seeks to demonstrate the pharmaceutical application of multidimensional scaling (MDS) by incorporating it as a pre-formulation tool for grouping an expanded range of microcrystalline celluloses (MCC). MDS presents the various MCC grades in two-dimensional space based on their torque rheological properties; thus conferring an extra dimension to the pre-formulation tool to facilitate the visualization of the relative positions of each MCC grade. Through this work, the utility of MDS for expediting pre-formulation studies, in particular, grouping of excipients that are available in different brands and grades can be amply exemplified.
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  • Anthraquinones from Ophiorrhiza hayatana OHWI
    Hsiu-Hui Chan, Chia-Ying Li, Amooru Gangaiah Damu, Tian-Shung Wu
    2005 Volume 53 Issue 10 Pages 1232-1235
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1232
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    Three new naturally occurring anthraquinones, ophiohayatone-A (1), -B (2), and -C (3), together with four known anthraquinones, were isolated from Ophiorrhiza hayatana OHWI (Rubiaceae). Structures of these new compounds were established by spectral methods.
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  • Design, Synthesis, and Structure–Activity Relationships of 3,4-Dihydropyridopyrimidin-2(1H)-one Derivatives as a Novel Class of Sodium/Calcium Exchanger Inhibitor
    Hirohiko Hasegawa, Masami Muraoka, Mikiko Ohmori, Kazuki Matsui, Atsuy ...
    2005 Volume 53 Issue 10 Pages 1236-1239
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1236
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    Design, synthesis, and structure–activity relationships for 3,4-dihydropyridopyrimidin-2(1H)-one derivatives, which are aza-3,4-dihydro-2(1H)-quinazolinone derivatives, as the sodium/calcium (Na+/Ca2+) exchanger inhibitors are discussed. These studies based on 3,4-dihydro-2(1H)-quinazolinone derivatives led to the discovery of a structurally novel and potent Na+/Ca2+ exchanger inhibitor, 3,4-dihydropyridopyrimidin-2(1H)-one derivative (26), with an IC30 value of 0.02 μM. Compound 26 directly inhibited the Na+-dependent Ca2+ influx via the Na+/Ca2+ exchanger after Na+-free treatment in cardiomyocytes.
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  • Preparation and Evaluation of Solid Dispersion for Nitrendipine–Carbopol and Nitrendipine–HPMCP Systems Using a Twin Screw Extruder
    Liang Wang, Fu De Cui, Tomokazu Hayase, Hisakazu Sunada
    2005 Volume 53 Issue 10 Pages 1240-1245
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1240
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    In the present study, we prepared solid dispersions of the poorly water-soluble drug nitrendipine (NIT) using the twin screw extruder method with high-molecular-weight substances, hydroxypropylmethylcellulosephthalate (HPMCP) and Carbopol (CAR), as carriers. Powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC) evaluation showed that solid dispersions can be formed when NIT–HPMCP and NIT–CAR mixtures are treated with the twin screw extruder method. Fourier Transformation IR Spectroscopy (FT-IR) obtained with NIT–HPMCP and NIT–CAR solid dispersions indicated the presence of hydrogen bonding between the drug and the carriers. NIT–CAR solid dispersions were found to give somewhat higher dissolution than crystalline NIT and physical mixtures, while the dissolution of NIT–HPMCP solid dispersions was markedly decreased compared with the crystalline NIT and physical mixtures. These findings indicated that CAR has a greater ability to improve the dissolution of NIT than HPMCP when a twin screw extruder was employed to prepare the solid dispersions. The twin screw extruder method can be used as a simple and effective method for the preparation of solid dispersions to improve the dissolution properties of poorly water-soluble drugs when choosing proper polymers as carriers.
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  • Synthesis of Ibuprofen Eugenol Ester and Its Microemulsion Formulation for Parenteral Delivery
    Xiuli Zhao, Dawei Chen, Ping Gao, Pingtian Ding, Kexin Li
    2005 Volume 53 Issue 10 Pages 1246-1250
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1246
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    The purpose of this study was to investigate the possibility of parenteral delivery of poorly water-soluble lipophilic drugs using a phospholipid-based microemulsion system. Ibuprofen eugenol ester (IEE), a highly lipophilic compound, was synthesized from ibuprofen and eugenol, and isolated as an amorphous whitish solid with a melting point at 40.2±0.1 °C, which structure was confirmed by IR, 1H-NMR and MS spectra. A pharmaceutically acceptable microemulsion system using Miglyol 812, soybean phosphatidylcholine (SbPC) and poly (ethylene glycol) (660)-12-hydroxystearate (Solutol® HS-15), and PEG400 and ethanol as oil phase, surfactants and cosurfactants, respectively, was presented and characterized in terms of stability, droplet size distribution (DSD) and their solubilization capacity of IEE. The solubility of IEE in the optimized microemulsion formulation consisting of 6.4% ibuprofen eugenol, 9.6% Miglyol 812, 6% SbPC, 6% HS-15, 8.4% PEG400, 3.6% ethanol and 60% distilled water (w/w) was about 21000 times higher than that in water. The ibuprofen blood concentration after intravenous administration of microemulsions was determined and compared with that of ibuprofen solution. It was concluded that the presented microemulsion system might be a promising intravenous dosage form of poorly water-soluble lipophilic drugs.
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  • Fluorimetric Determination of Ascorbic Acid in Vitamin C Tablets Using Methylene Blue
    Yusuf Dilgin, Gürel Nişli
    2005 Volume 53 Issue 10 Pages 1251-1254
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1251
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    In this study, a simple and sensitive fluorimetric method was described for the determination of Ascorbic Acid (AA). The procedure is based on the reaction between AA and Methylene Blue (MB). The fluorescence intensity of MB was measured at excitation and emission of 664 and 682 nm, respectively. MB concentration was decreased as a function of decreasing fluorescence intensity due to forming colorless form of MB (Leuco-MB) in the reaction between AA and MB. A linear relationship was obtained between the decreasing fluorescence intensity and the concentration of AA in the range of 3.0×10−7—6.0×10−6 mol·l−1. The detection limit was 2.5×10−7 mol·l−1. The proposed method was applied successfully for the determination of AA in Vitamin C tablets.
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  • Biologically Active Glycosides from Asteroidea, 41. Isolation and Structure Determination of Glucocerebrosides from the Starfish Linckia laevigata
    Tomoki Maruta, Takeshi Saito, Masanori Inagaki, Osamu Shibata, Ryuichi ...
    2005 Volume 53 Issue 10 Pages 1255-1258
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1255
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    A new glucocerebroside, linckiacerebroside A (1) and a known glucocerebroside S-2a-3 (2), have been isolated from the cerebroside molecular species obtained from the less polar fraction of the CHCl3/MeOH extract of the starfish Linckia laevigata, together with three pseudo homogeneous glucocerebroside, 3, 4, and 5. The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidence.
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  • Solvolysis of (4,5)-anti-4-Aryl-5-tosyloxy-2(E)-hexenoate Derivatives
    Machiko Ono, Takeru Ehara, Hirofumi Yokoyama, Nobuyoshi Ohtani, Youko ...
    2005 Volume 53 Issue 10 Pages 1259-1265
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1259
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    The solvolysis reaction of (4,5)-anti-4-aryl-5-tosyloxy-2(E)-hexenoates 4a—k gave (4,5)-anti-4-aryl-5-hydroxy-2(E)-hexenoates 2a—k and (4,5)-anti-5-aryl-4-hydroxy-2(E)-hexenoates 5a—k along with the complete inversion. This 1,2-aryl migration was induced by treatment with heating in water-saturated nitromethane. On the basis of the substituent effect on the aromatic ring, this 1,2-aryl migration is thought to proceed via the σ-bridged phenonium ion. The product selectivity between 2a—k and 5a—k was found to be subtly governed by the substituent and substitution pattern in the aromatic ring of the substrates 4a—k.
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  • Palladium-Catalyzed Allylation of Acidic and Less Nucleophilic Anilines Using Allylic Alcohols Directly
    Yi-Chun Hsu, Kim-Hong Gan, Shyh-Chyun Yang
    2005 Volume 53 Issue 10 Pages 1266-1269
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1266
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    The direct activation of C–O bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isoproxide and 4 Å molecular sieves. The acidic and less nucleophilic anilines such as diphenylamine, phenothiazine, 4-cyanoaniline, and nitroanilines are efficiently allylated under palladium catalysis using allylic alcohols as allylating reagents.
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  • Sub- and Supercritical Chiral Separation of Racemic Compounds on Columns with Stationary Phases Having Different Functional Groups
    Hiroko F. Kasai, Masayoshi Tsubuki, Sohichiro Matsuo, Toshio Honda
    2005 Volume 53 Issue 10 Pages 1270-1276
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1270
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    Separation of the enantiomers of each of three different racemates, neutral rac-α-tetralol, acidic rac-2-phenylpropionic acid, and basic rac-1-phenylethylamine, using subcritical and supercritical fluid chromatography with two different chiral stationary phases, heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (Sumichiral OA-7500 column) and tris(3,5-dimethylphenylcarbamate) of amylose (Chiralpak AD-H column), was compared. The elution order of the enantiomers of the three racemates was determined, and the effects of the type of alcohol modifier, column oven temperature, mobile phase composition, flow rate, and pressure were examined. The most appropriate column oven temperature depended on both the type of alcohol modifier and the compound analyzed. Lower alcohol content improved the peak separation of both rac-α-tetralol on the Sumichiral OA-7500 column and rac-1-phenylethylamine on the Chiralpak AD-H column, while the same phenomenon was not observed with either rac-α-tetralol or rac-2-phenylpropionic acid on the Chiralpak AD-H column. Decreasing outlet pressure improved the peak separation obtained with rac-2-phenylpropionic acid, but had little effect on either rac-α-tetralol or rac-1-phenylethylamine.
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  • Synthesis of Linear Tripeptides for Right-Hand Segments of Complestatin
    Yaeko Yamada, Ai Akiba, Shiho Arima, Chiharu Okada, Kiminari Yoshida, ...
    2005 Volume 53 Issue 10 Pages 1277-1290
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1277
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    This paper concerns a synthetic study of the right-hand segment of complestatin, an inhibitor of gp120-CD4 receptor. The effective synthesis of four important precursors for the right-hand segment of complestatin is described. Two of them are the precursor tripeptides for macrolactamization to the right-hand segment of complestatin at the last step and the other two are the precursor tripeptides for ring-closing reaction using Suzuki and Stille coupling, respectively, to the right-hand segment of complestatin at the last step. These compounds and the synthetic procedure will serve for both the synthesis of the right-hand segment and total synthesis of complestatin in the near future. In addition, consideration of the smooth acidic isomerization of complestatin to chloropeptin was carried out by density functional theory (DFT) calculation.
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  • Crystal Structures of Palladium(II) Ternary Complexes of 5-X-2-Aminobenzoic Acid with 1,10-Phenanthroline and Their Interaction with Calf Thymus DNA (Where X=Cl, Br and I)
    Yue Wang, Nobuo Okabe, Mamiko Odoko
    2005 Volume 53 Issue 10 Pages 1291-1295
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1291
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    The crystal structures of a series of three palladium(II) ternary complexes of 5-halogeno-2-aminobenzoic acid (5-X-AB, where X=Cl, Br and I) with 1,10-phenanthroline [Pd(5-Cl-AB)(phen)] (1), [Pd(5-Br-AB)(phen)] (2) and [Pd(5-I-AB)(phen)] (3) have been determined, and their coordination geometries and the crystal architecture characterized. All of the complexes are an isostructure in which each Pd(II) atom has basically similar square planar coordination geometry. The substitute halogen group at 5-position of AB plays an important role in producing the coordination bonds of the carboxylate and amino groups in which the carboxylate O atom and the amino N atom act as the negative monodentate ligand atoms. The coordination bond distances of O–Pd increase in the order 1<2<3, while those of N–Pd decrease in the same order. The binding of the complexes to the calf thymus DNA has also been studied by the fluorescence method. Each of the complexes shows high binding propensity to DNA which can be reflected as the relative order 1<2<3.
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  • Prediction of Solvents Suitable for Crystallization of Small Organic Molecules
    Kozo Hosokawa, Junichi Goto, Noriaki Hirayama
    2005 Volume 53 Issue 10 Pages 1296-1299
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1296
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    Selection of suitable solvent is essential for crystallization of pharmaceuticals. Based on chemical structures of 6397 compounds and 15 single solvents that were used to obtain their single crystals, correlations between the molecular characteristics and the solvents have been investigated by cheminformatics methods. Decision-tree and Bayesian-probability methods have been applied to make classification models. These two models are complementary in character in the present case. It has been proven that the prediction of the solvent rankings for particular compounds by use of the classification models is satisfactory from the practical point of view. The present study has demonstrated that cheminformatics methods could greatly help rational crystallization of small organic molecules such as pharmaceuticals.
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  • Methyl Migrated Cassane-Type Furanoditerpenes of Caesalpinia crista from Myanmar
    Surya Kant Kalauni, Suresh Awale, Yasuhiro Tezuka, Arjun Hari Banskota ...
    2005 Volume 53 Issue 10 Pages 1300-1304
    Published: 2005
    Released on J-STAGE: October 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.1300
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    From the CH2Cl2 extract of seed kernels of Caesalpinia crista from Myanmar, two rare and biogenetically interesting methyl migrated cassane-type furanoditerpenes [caesalpinins MM (1) and MN (2)] and two normal cassane-type furanoditerpenes [caesalpinins MO (3) and MP (4)] have been isolated, together with eight known cassane-type diterpenes, 1-deacetoxy-1-oxocaesalmin C (5), 1-deacetylcaesalmin C (6), caesalmin C (7), bonducellpin C (8), caesaldekarin e (9), 2-acetoxycaesaldekarin e (10), 2-acetoxy-3-deacetoxycaesaldekarin e (11), and norcaesalpinin E (12). Among the known compounds, compounds 5 and 6 were for the first time isolated from a natural source. The structures of these compounds were elucidated by the use of spectroscopic techniques.
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