Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
50 巻, 7 号
選択された号の論文の26件中1~26を表示しています
Regular Articles
  • Toshio Oguchi, Yuichi Tozuka, Takehisa Hanawa, Mayuko Mizutani, Nahomi ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 887-891
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    The solid-state complexation between cholic acid (CA) and either methyl p-hydroxybenzoate (MPB) or ibuprofen (IBP) was investigated. Powder X-ray diffractometry, IR spectroscopy and thermal analysis suggested the complex formation between CA and MPB as well as between CA and IBP by co-grinding method. The stoichiometry of CA–MPB was 1 : 1 while that of CA–IBP was 2 : 1, reflecting the effect of guest size on complex formation. The guest compounds were assumed to be included in the channel of complexes formed by hydrogen bonds among CA molecules.
  • Chellan Vijaya Raghavan, Chithambaram Muthulingam, Joseph Amaladoss Jo ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 892-895
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    The colon specific drug delivery systems based on polysaccharides; locust bean gum and chitosan in the ratio of 2 : 3, 3 : 2 and 4 : 1 were evaluated using in vitro and in vivo methods. The in vitro studies in pH 6.8 phosphate buffer containing 2% w/v rat caecal contents showed that the cumulative percentage release of mesalazine after 26 h were 31.25±0.56, 46.25±0.96, 97.5±0.26 (mean±S.D.), respectively. The in vivo studies conducted in nine healthy male human volunteers for the various formulations revealed that, the drug release was initiated only after 5 h (i.e.) transit time of small intestine and the bioavailability (AUC0→t*) of the drug was found to be 85.24±0.10, 196.08±0.12, 498.62±0.10 μg h/ml 26 (mean±S.D.), respectively. These studies on the polysaccharides demonstrated that the combination of locust bean gum and chitosan as a coating material proved capable of protecting the core tablet containing mesalazine during the condition mimicking mouth to colon transit. In particular, the formulation containing locust bean gum and chitosan in the ratio of 4 : 1 held a better dissolution profile, higher bioavailability and hence a potential carrier for drug targeting to colon.
  • Li-hua Xie, Xuan Wang, Purusotam Basnet, Naoko Matsunaga, Seiichi Yama ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 896-899
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    Micellar electrokinetic chromatography (MEKC) conditions were developed to analyze the constituents of Scutellariae Radix (SR) and Scutellaria baicalensis roots. Using the MEKC method, the major flavonoid constituents of baicalin, baicalein and wogonin of wild and cultivated S. baicalensis roots were compared. In a preliminary comparison of electropherogram, one special peak was found in a wild sample but not in a 2-year-cultivated one. The compound corresponding to the peak was isolated and identified as a phenylethanoid glycoside, acteoside, by comparing the 1H- and 13C-NMR spectral data with that of the authentic compound. This is the first time acteoside has been isolated from the Scutellaria genus. It could only be found in SR derived from wild S. baicalensis roots and 4-year-cultivated plants, but not in plant materials cultivated for 3 years. Applying the MEKC method established in this study, rapid and simultaneous determinations of acteoside together with 3 flavonoids in samples were achieved. The method can thus be used for the quality control of SR in a shorter analysis period than HPLC.
  • Da Wei Li, Eun Bang Lee, Sam Sik Kang, Jin Ee Hyun, Wan Kyun Whang
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 900-903
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    By bioassay-guided separation, a known saponin, kalopanaxsaponin A (1) and a new saponin, pictoside A (2) were isolated from the stem bark of Kalopanax pictus as anti-inflammatory components when evaluated by vascular permeability test. Another novel saponin, pictoside B (3) was also isolated but was inactive in the test system used. The structures of pictosides A and B were elucidated as caulophyllogenin 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside (2) and pictogenin (3β,6β,16α,23-tetrahydroxyolean-12-ene-28-oic acid) 3-O-α-L-arabinopyranoside (3), respectively, by spectral analysis and by chemical degradation. Kalopanaxsaponin A and pictoside A showed significant anti-inflammatory activity at the oral doses of 50 mg/kg.
  • Eleni Rekka, Michael Chrysselis, Ioanna Siskou, Angeliki Kourounakis
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 904-907
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    The relationship between free radicals and acute or chronic inflammation has been well established. We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. Furthermore, some synthetic azulene analogues have been found to possess anti-inflammatory activity. In this investigation we report the synthesis of five 3-alkyl or 3-(hydroxy)alkylazulene-1-carboxylic acids and esters, from tropolone, via the corresponding furanone. The synthesised compounds were tested for their effect on the peroxidation of rat hepatic microsomal membrane lipids, applying the 2-thiobarbituric acid test. Their anti-inflammatory activity was evaluated in vitro by the offered inhibition of soybean lipoxygenase. All the tested molecules were found to inhibit lipid peroxidation by 100% at 1 mM. They were also found to considerably inhibit lipoxygenase activity. The above results are discussed in relation to the structure and physicochemical properties of the examined azulene derivatives.
  • Tomio Shimizu, Masaya Ishizaki, Nobuo Nitada
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 908-921
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    The regio- and stereoselectivity of the 1,3-dipolar cycloaddition reactions of C-aryl-N-alkylaldonitrones (1a—e) with some alkenes were found to be affected significantly by the addition of Lewis acid. The rate of the reaction was also affected by adding the Lewis acid. In the reactions using allyl alcohol as a dipolarophile an addition of Lewis acid caused a remarkable acceleration of the reaction and a great change in the stereoselectivity. In the reactions using ethyl acrylate as a dipolarophile the regioselectivity was reversed whether the reaction was performed in the presence or the absence of Lewis acid; i.e. isoxazolidine-5-carboxylates were obtained mainly in the absence of Lewis acid although isoxazolidine-4-carboxylates were obtained mainly in the presence of Lewis acid. When the reaction of C,N-diarylaldonitrones (1k, 1m, 1n) with ethyl acrylate was carried out in the presence of Lewis acid, the cleavage of the N–O bond of the cycloadducts giving γ-aminoalcohols was also observed besides a reverse phenomenon of regioselectivity.
  • Toshihiko Kaneko, Richard S. J. Clark, Norihito Ohi, Tetsuya Kawahara, ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 922-929
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    During a search for novel, orally-active inhibitors of upregulation of adhesion molecules such as intercellular adhesion molecule-1 (ICAM-1), we found a new series of 10H-pyrazino[2,3-b][1,4]benzothiazine derivatives to be potent ICAM-1 inhibitors. Of these compounds, N-[1-(10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)piperidin-4-yl]-N′,N′-dimethylsulfamide 7p showed the potent oral inhibitory activities against neutrophil migration in a murine interleukin-1 (IL-1) induced paw inflammation model. The synthesis and structure–activity relationships of these amide derivatives are described.
  • Masako Kinoshita, Mahisa Ohtsuka, Daisuke Nakamura, Hiroyuki Akita
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 930-934
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    First synthesis of (+)-α-polypodatetraene (1) and (+)-γ-polypodatetraene (2) was achieved from (+)-albicanol (6) and (−)-drimenol (8), respectively. The absolute structure of natural (+)-2 was established to be (5S,9S,10S)-polypoda-7,13(E),17(E),21-tetraene.
  • Naoko Morisaki, Hisayoshi Kobayashi, Yumiko Yamamura, Masuo Morisaki, ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 935-940
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    Steroidal allylic alcohols formed Na+ adduct ion peaks [M+Na]+ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na+. The adduct ion was stable and did not undergo dehydroxylation. We suggest that the Na+ adduction will be useful for the molecular weight determination of allylic alcohols which are susceptible to dehydroxylation under FAB mass spectrometric conditions. Na+ adduct ions of α,β-unsaturated carbonyl compounds were also investigated.
  • Yoshimi Hirokawa, Hiroshi Harada, Takashi Yoshikawa, Naoyuki Yoshida, ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 941-959
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    In search of a dopamine D2 and serotonin 5-HT3 receptors dual antagonist as a potential broad antiemetic agent, a number of benzamides were prepared from 4-amino-5-chloro-2-methoxybenzoic acid derivatives and 6-amino-1,4-dialkylhexahydro-1,4-diazepines and evaluated for their binding affinity for the dopamine D2 and the serotonin 5-HT3 receptors using rat brain synaptic and rat cortical membranes, respectively. From the results of both in vitro receptor binding and in vivo biological assays for the dopamine D2 receptor, 1-ethyl-4-methylhexahydro-1,4-diazepine ring was selected as an optimum amine moiety. Introduction of one methyl group on the nitrogen atom at the 4-position and/or modification of the substituent at the 5-position of the 4-amino-5-chloro-2-methoxybenzoyl moiety caused a marked increase in the dopamine D2 receptor binding affinity along with a potent 5-HT3 receptor binding affinity. Among the compounds, 5-chloro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-2-methoxy-4-methylaminobenzamide (82), 5-bromo (110), and 5-iodo (112) analogues exhibited a much higher affinity for the dopamine D2 receptor than that of metoclopramide (IC50=17.5—61.0 nM vs. 483 nM). In particular, 82 showed a potent antagonistic activity for both receptors in vivo tests. Optical resolution of the racemate 82 brought about a dramatic change in the pharmacological profile with the (R)-enantiomer exhibiting a strong affinity for both the dopamine D2 and the 5-HT3 receptors, while the corresponding (S)-enantiomer had a potent and selective serotonin 5-HT3 receptor binding affinity.
  • Hiromitsu Takayama, Hayato Ishikawa, Mariko Kitajima, Norio Aimi
    原稿種別: Regular Article
    専門分野: [not specified]
    2002 年 50 巻 7 号 p. 960-963
    発行日: 2002年
    公開日: 2002/07/01
    ジャーナル フリー
    Lead tetraacetate oxidation of a Corynanthe-type indole alkaloid, mitragynine, produced mainly 7-acetoxyindolenine derivative (2) together with a dimeric compound (4) as a minor product. The novel structure having a bridge between the C-11′ and C-7 positions in the respective indolenine parts and its formation mechanism were studied.
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