Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 61, Issue 8
Displaying 1-14 of 14 articles from this issue
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  • The Epoxidation of the Olefins by meso-Tetraphenylporphyrinatochromium(3+) Chloride as an Electrochemical P-450 Model Compound
    Takashi Michida, Takuryu Omichi
    2013 Volume 61 Issue 8 Pages 799-801
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-00806
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    An electrochemical P450 model compound consisting of meso-tetraphenylporphyrinatochromium(3+) chloride (CrTPP), imidazole, and acetic acid was used in acetonitrile containing alkenes. The corresponding epoxides were obtained in better yields compared to a similar electrochemical P450 model compound using meso-tetraphenylporphyrinatomanganese(3+) chloride. The results of cyclic voltammetry and controlled potential electrolysis suggest that electrochemically reduced CrTPP reacts with dissolved oxygen to oxidize alkenes to epoxides.
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  • Fingerprint Analysis and Simultaneous Determination of Phenolic Compounds in Extracts of Curculiginis Rhizoma by HPLC-Diode Array Detector
    Qingya Bian, Hui Yang, Chi-on Chan, Dengping Jin, Daniel Kam-Wah Mok, ...
    2013 Volume 61 Issue 8 Pages 802-808
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01058
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    Curculiginis Rhizoma (Curculigo orchioides GAERTN.) is a well-known Chinese herbal medicine, as well as an important Rasayana drug in India. Current criteria of quality control on this herb are to quantitatively analyze single compound curculigoside, which fail to comprehensively evaluate quality of this herb. In this paper, a simple and reliable HPLC coupled with diode array detector (DAD) method was developed to evaluate the quality of Curculiginis Rhizoma through establishing chromatographic fingerprint and simultaneously quantitating four phenolic compounds, orcinol glucoside, orcinol, 2,6-dimethoxybenzoic acid and curculigoside. The fingerprint displayed eleven common peaks, and the similarity index of different samples was in a range of 0.890–0.977. Validation of the method was acceptable, with 96.03–102.82% accuracy in recovery test and inter and intra-day precisions were less than 2%. This developed method by having a combination of chromatographic fingerprint and quantitation analysis could be applied to the quality control of Curculiginis Rhizoma.
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  • Quetiapine Free Base Complexed with Cyclodextrins to Improve Solubility for Parenteral Use
    Noriko Ogawa, Mayumi Kaga, Tomohiro Endo, Hiromasa Nagase, Takayuki Fu ...
    2013 Volume 61 Issue 8 Pages 809-815
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00157
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    Quetiapine, an antipsychotic drug used for schizophrenia treatment, is poorly water soluble, and therefore, administration of the more water-soluble quetiapine fumarate is preferred. Absorption of quetiapine through biological membranes may be improved by enhancing the solubility of the quetiapine base, the non-ionic form. In this study, the currently used salt form was converted into the free base (oily material). We employed cyclodextrins (CDs) as pharmaceutical additives to improve the solubility of the quetiapine base. The formation of quetiapine–β-cyclodextrin (β-CD) complexes was studied by phase solubility studies, continuous variation method, NMR spectroscopy, and powder X-ray diffraction. The formation of a poorly water-soluble complex was confirmed by the phase solubility study, and the interaction between quetiapine and β-CD in water was confirmed by NMR spectroscopy. In addition, the effects of β-CD derivatives (glucosyl-β-CD, maltosyl-β-CD, 2-hydroxypropyl-β-CD, dimethyl-β-CD, and trimethyl-β-CD) on the solubility of the quetiapine base were studied. The findings indicated that the aforementioned hydrophilic β-CD derivatives could be used as pharmaceutical additives of quetiapine for parenteral formulations as a result of the improved solubility of the quetiapine base because of inclusion complexation. Therefore, converting the currently used salt form into the free base, investigating the free base as a candidate for CD inclusion, and converting the oily material such as the free base into a powder by forming an inclusion complex that is easy to deal with is considered a worthwhile approach that may lead to novel formulations of the drug in question.
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  • Culcitiolides E–J, Six New Eremophilane-Type Sesquiterpene Derivatives from Senecio culcitioides
    Taichi Mitsui, Ken-ichiro Hayashi, Mikiko Kawai, Masahiro Kido, Hiroyu ...
    2013 Volume 61 Issue 8 Pages 816-822
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00243
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    Culcitiolides E–J (1–6), six new eremophilane-type sesquiterpenes, were isolated from the stem of Senecio culcitioides SCH. BIP. (Asteraceae). The structures were determined by detailed NMR spectral analysis. The inhibitory activities of these compounds against nuclear factor κB (NF-κB)-dependent gene expression were assessed. Culcitiolides E, H, and I potently inhibited NF-κB-induced gene expression at 20 µM.
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  • Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives
    Nobuko Mibu, Kazumi Yokomizo, Satoshi Takemura, Nami Ueki, Saki Itohar ...
    2013 Volume 61 Issue 8 Pages 823-833
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00308
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    We describe the synthesis and biological evaluation of newly designed 2,4,6-trisubstituted symmetrical 1,3,5-triazine (TAZ) derivatives. Among the tested trisubstituted symmetrical TAZ derivatives, various C3- or CS-symmetrical alkoxy-amino-substituted TAZ derivatives showed significant antiviral activity against herpes simplex virus type 1 (HSV-1) and/or cytotoxic activity against Vero cells. The structure–activity relationships for anti-HSV-1 activity of these symmetrical 2,4,6-trisubstituted TAZ derivatives are also described. Experimental results indicated that a CS-symmetrical TAZ structure with introduction of two alkoxy groups and one amine moiety seems to be the minimally required structure for anti-HSV-1 activity.
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  • Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and in Vitro Studies
    Fatma Abdel-Fattah Ragab, Nagwa Mohamed Abdel-Gawad, Hanan Hanna Georg ...
    2013 Volume 61 Issue 8 Pages 834-845
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00314
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    Some 1-(4-chlorophenyl or benzenesulfonamide)-2,3- and/or 4-substituted-1H-pyrazol-5(4H)-one derivatives were synthesized and screened for their anti-inflammatory and analgesic activities, in addition to their ulcerogenic liability. They were found to be active as anti-inflammatory and analgesic agents. Compound 6b was found to be the most active as anti-inflammatory agent and compound 9b was found to be the most active one as anti-inflammatory and analgesic agent. On the other hand, cyclooxygenase-1/-2 (COX-1)/COX-2 isozyme selectivity was also done and the tested compounds showed equal inhibition to both isoforms. Moreover, 2D-quantitative structure–activity relationship (QSAR) studies revealed well predictive and statistically significant and cross validated QSAR model that helps to explore some expectedly potent compounds.
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  • Synthesis of Am80 (Tamibarotene) Prodrug Candidates, Congeners and Metabolites
    Hideaki Muratake, Yohei Amano, Takahiro Toda, Kiyoshi Sugiyama, Koichi ...
    2013 Volume 61 Issue 8 Pages 846-852
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00356
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    Compound 1 (IT-M-07000) was previously reported as a candidate prodrug of Am80 (Tamibarotene; used to treat acute promyelocytic leukemia), and shown to be efficiently metabolized to Am80 via β-oxidation. Here, we describe in detail the synthesis of 1, together with another tetradeuterated candidate prodrug, IT-YA-00616 (2), as well as two congeners, and several metabolic intermediates of 1 previously detected in mouse plasma.
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  • Preparation of Tricyclic Lactam Model Compounds of Renieramycin and Saframycin Anticancer Natural Products from Common Intermediate
    Keiyo Nakai, Masashi Yokoya, Naoki Saito
    2013 Volume 61 Issue 8 Pages 853-869
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00361
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    Tricyclic lactam model compounds of the left half (ABC ring) of renieramycin and saframycin anticancer natural products were prepared from common intermediate 6a. Readily available alcohol 6a was converted into enamide 8, and this was followed by transformation into 6b through a hydrobromination reaction in a stereoselective manner. Some diastereomers at C-6 to C-11a of the tricyclic lactam model compounds having several functional groups at C-6 were prepared from 6a or 6b in good yields. We presented also an unexpected reductive acetylation of the p-quinone to produce the corresponding 3,4-dehydro derivative.
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Notes
  • The Effect of Indium(III) Triflate in Oxone-Mediated Oxidative Methyl Esterification of Aldehydes
    Tomoko Mineno, Mai Sakai, Akira Ubukata, Kazuhide Nakahara, Hitoshi Yo ...
    2013 Volume 61 Issue 8 Pages 870-872
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00072
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    An oxidative methyl esterification of aldehydes was effectively achieved. The trivalent indium reagent, indium(III) triflate, was revealed to accelerate the reactions in many cases. Aromatic aldehydes with various substituents were subjected to this method, and each produced the corresponding methyl esters in good to excellent yields within a relatively short reaction time.
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  • Study on Antitubercular Constituents from the Seeds of Nigella glandulifera
    Lian-li Sun, Ming Luan, Wei Zhu, Shuai Gao, Qian-lan Zhang, Chan-juan ...
    2013 Volume 61 Issue 8 Pages 873-876
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    Advance online publication: May 24, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00216
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    Two new compounds with five known compounds have been isolated from EtOH extract of the seeds of Nigella glandulifera. On the basis of their spectroscopic and chemical evidence, the new compounds were elucidated as methoxynigeglanine (1) and 6-methoxythymol-3-O-β-D-glucopyranoside (4). Compounds 1–4 showed moderate antitubercular activity against Mycobacterium tuberculosis strain H37Rv with minimal inhibitory concentration (MIC) values of 32–250 µg/mL.
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  • Synthesis and Biopharmaceutical Studies of JLTN as Potential Dasatinib Prodrug
    Fei Liu, Li-Wei Lang, Ji Jiang, Hua-Jun Lu, Jian-Min Wang, Shih-Chen W ...
    2013 Volume 61 Issue 8 Pages 877-881
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    Advance online publication: May 16, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00248
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    Dasatinib was identified as a potent orally administered Src/Abl kinase inhibitor with excellent antiproliferative activity against Philadelphia chromosome-positive chronic myelogenous leukemia in chronic phase. The low bioavailability of Dasatinib may be due to both incomplete oral absorption and first-pass metabolism. A prodrug, JLTN, was synthesized to minimize the first-pass effect of Dasatinib and improve the oral bioavailability following oral administration via targeting intestinal peptide transporter and enhancing chemical stability. Biological evaluation data indicated that there was a 150%-fold increase in oral bioavailability of this prodrug compared to the parent drug Dasatinib in monkeys.
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  • Study of 1,3,5-Triazine-Based Catalytic Amide-Forming Reactions: Effect of Solvents and Basicity of Reactants
    Munetaka Kunishima, Masanori Kitamura, Hiroyuki Tanaka, Ichiro Nakakur ...
    2013 Volume 61 Issue 8 Pages 882-886
    Published: August 01, 2013
    Released on J-STAGE: August 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00368
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    Supplementary material
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    Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid–base equilibrium among reactants. In dichloromethane, a representative aprotic solvent, a strongly basic catalyst gave amides in higher yields than weakly basic catalysts, regardless of the basicity of the acid neutralizer, which is called the proton capture agent (PCA). In contrast, in protic solvents, such as methanol or aqueous methanol, weakly basic catalysts gave amides in somewhat better yields than the strongly basic catalysts. In general, PCAs with weakly basic properties are favorable, because those with strongly basic properties tend to give byproducts arising from the reaction between CDMT and the substrate amine.
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