Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 53, Issue 2
Displaying 1-24 of 24 articles from this issue
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Regular Articles
  • Epoxidation with an Electrocatalytic P-450 Model System in an Acidic Solution
    Takashi Michida, Chika Saiki, Chie Yamasaki, Yumiko Yamaoka
    2005 Volume 53 Issue 2 Pages 151-152
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.151
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    An electrochemical P-450 model system using meso-tetraphenylporphyrinatomanganese(III) chloride (MnTPP), imidazole and acetic acid was tested in an acetonitrile solution, and epoxide was obtained with a good current efficiency. The results of cyclic voltammetry revealed that acid plays an important role in the second electron transfer.
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  • Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. III. Synthesis and Antitumor Activity of 3-Phenylpiperazinyl-1-trans-propenes
    Hiroyuki Naito, Satoru Ohsuki, Ryo Atsumi, Megumi Minami, Mineko Mochi ...
    2005 Volume 53 Issue 2 Pages 153-163
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.153
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    A series of novel 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor activity against some tumor models when administered both intraperitoneally and orally. Compounds with the 3-chloropyridin-2-yl group (9g) and the 3-fluoro-5-substituted phenylpiperazinyl group (29b, c, and e) showed significantly potent cytotoxicity by in vitro testing. Among them, the 3-cyano-5-fluorophenyl derivative (29b) exhibited potent antitumor activity against several tumor cells including human carcinoma without causing undesirable effects in mice.
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  • Neoclerodane Diterpenoids from Ajuga taiwanensis
    Yu-Yi Chan
    2005 Volume 53 Issue 2 Pages 164-167
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.164
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    Phytochemical investigation of Ajuga taiwanensis resulted in the isolation of seven neoclerodane diterpenes, four of which ajugalide-A (1), -B (2), -C (3), and -D (4), are new and the remaining three are known diterpenes, ajugamacrin B (5), ajugapantin A (6), and ajugamarin C1 (7). Their structures were elucidated in spectral and chemical transformation studies.
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  • New Sphingolipids and a Sterol from a Lobophytum Species of the Indian Ocean
    Pendyala Muralidhar, Muthyala Muralikrishna Kumar, Nallamothu Krishna, ...
    2005 Volume 53 Issue 2 Pages 168-171
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.168
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    Chemical investigation of a soft coral species of the genus Lobophytum has resulted in the isolation of three new sphingolipids—(2S,3S,4R)-2-nonadecanoylamino-octadecane-1,3,4-triol (1), (2S,3R,4E,8E)-[(2′R)-2′-hydroxyheptadecanoylamino]-4,8-octadecadiene-1,3-diol (2), 1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2′R)-2′-hydroxynonadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol (3) and a sterol—(24S)-ergost-5-en-3β,7β-diol (4) along with the known sphingolipid—(2S,3R,4E,8E)-2-hexadecanoylamino-4,8-octadecadien-1,3-diol (5) which showed cytotoxicity against human peripheral blood mononuclear cells (PBMC).
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  • Quantitative Determination Method for Trace Amount of Penicillin Contaminants in Commercially Available Drug Product by HPLC Coupled with Tandem Mass Spectrometry
    Wataru Takada, Toshikazu Adachi, Noriaki Kihara, Satoshi Kitamura, Ter ...
    2005 Volume 53 Issue 2 Pages 172-176
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.172
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    A quantitative determination method for trace amount of penicillin contaminants in an active pharmaceutical ingredient (API) has been developed. Selective extraction of penicillin contaminants from the matrix containing API and specific separation among penicillin contaminants were achieved through an on-line column switching technique with gradient elution, followed by tandem mass spectrometric determination. Validation was conducted on the developed method in terms of specificity, linearity, accuracy, precision, and detection limit, and appeared reasonable. The detection limit was estimated as 0.03 ng/ml or lower of the concentration of penicillin contaminants in the preparation, corresponding to 4 parts par billion (ppb) against the API. This fulfilled the regulatory requirement by the authorities.
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  • A Dammarane Glycoside Derived from Ginsenoside Rb3
    Kejiang He, Yong Liu, Yi Yang, Peng Li, Ling YAng
    2005 Volume 53 Issue 2 Pages 177-179
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.177
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    A dammarane glycoside, designated compound Mx (C-Mx), was isolated from the hydrolysate of 20(S)-protopanaxadiol type ginsenosides containing G-Rb3 from Panax notoginseng leaves with crude snailase. Its chemical structure was elucidated to be 20-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl-20(S)-protopanaxadiol on the basis of spectral analysis. Its cytotoxicity against breast cancer cell line MCF-7 and effects on the sensitivity to doxocubicin of doxocubicin-resistant MCF-7 cells were also investigated. The new compound showed moderate cytotoxicity and partial reversal of doxocubicin resistance.
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  • Water Vapor Adsorption Behavior of Sodium Deoxycholate Anhydrous Forms
    Makoto Ono, Hiroyuki Anzai, Yuichi Tozuka, Kunikazu Moribe, Toshio Ogu ...
    2005 Volume 53 Issue 2 Pages 180-183
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.180
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    Pseudopolymorphism of sodium deoxycholate (NaDC) was investigated. Intact NaDC (dihydrate) was dried at 60 °C under reduced pressure resulting an anhydrous amorphous phase. On the other hand, intact NaDC was altered to an anhydrous crystalline form by heating at 200 °C. The water vapor adsorption and desorption isotherms of dehydrated NaDCs were determined using an automatic gravimetric water vapor adsorption analyzer. In the case of NaDC dehydrated at 60 °C, the weight was increased in rising relative humidity and it was transformed into the NaDC tetrahydrate above 60% RH, which was identified by TG/DTA and powder X-ray diffraction. During the water vapor adsorption process of the sample dehydrated at 200 °C, the NaDC dihydrate was obtained in the range of 50 to 70% RH and then transformed into the NaDC octahydrate above 85% RH. The NaDC octahydrate was characterized by TG/DTA and powder X-ray diffraction for the first time. During the desorption process, the octahydrate was changed to the tetrahydrate between 80 and 40% RH.
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  • Discovery of a Novel and Potent Human and Rat β3-Adrenergic Receptor Agonist, [3-[(2R)-[[(2R)-(3-Chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetic Acid
    Hiroshi Harada, Yoshimi Hirokawa, Kenji Suzuki, Yoichi Hiyama, Mayumi ...
    2005 Volume 53 Issue 2 Pages 184-198
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.184
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    In search for potent and selective β3-adrenergic receptor (β3-AR) agonists as potential drugs for the treatment of type II diabetes and obesity, a novel series of 1-(3-chlorophenyl)-2-aminoethanol derivatives were prepared and evaluated for their biological activity at human β1-, β2-, and β3-ARs and rat β3-AR expressed in Chinese hamster ovary (CHO) cells. Replacement of the right-hand side (RHS, benzene ring) in the ‘first generation’ β3-AR agonists BRL 37344 and CL 316243 with a 1H-indole ring gave compound 31 with unique pharmacological properties among β3-AR agonists. Initial in vitro assays showed that 31 possesses modest rat and human β3-ARs agonistic activity. Introduction of various substituent into the indole nucleus of 31 afforded a number of compounds with good β3-ARs agonistic activity. In particular, 90 having a carboxylic acid functionality at the 7-position of the indole nucleus showed the most potent human β3-AR agonistic activity. Finally, optical resolution of 90 led to the identification of the most promising compound, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetic acid (96, AJ-9677). This compound exhibited potent human β3-AR agonistic activity (EC50=0.062 nM, IA=116%) with 210- and 103-fold selectivity over human β2-AR and β1-AR, respectively. Compound 96 also exhibited potent rat β3-AR agonistic activity (EC50=0.016 nM, IA=110%). Moreover, repeated oral administration of 96 inhibited body weight gain and significantly decreased glucose, insulin, free fatty acid, and triglyceride concentrations in plasma in KK-Ay/Ta mice. On the basis of this pharmacological profile, 96 entered clinical development as a drug for the treatment of type II diabetes and obesity.
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  • Reactions of 1-Naphthols with π-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation
    Tetsuya Takeya, Hiromu Kondo, Tsuyoshi Otsuka, Hirohisa Doi, Iwao Okam ...
    2005 Volume 53 Issue 2 Pages 199-206
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.199
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    We investigated the reactions of various 1-naphthols (NPOHs; 1) with p-benzoquinones (Qs), such as 1,4-benzoquinone (BQ) and p-chloranil (CA), as π-electron acceptors. With electron-rich NPOHs 1a—c, oxidative biaryl coupling and subsequent dehydrogenation reaction took place selectively to give the corresponding 2,2′-binapthyl-1,1′-quinones 3a—c in excellent yield. In the case of electron-deficient NPOHs 1e, f, two different types of reactions occurred in the presence of SnCl4 and ZrO2 under similar conditions: SnCl4 mediated oxidative dimerization and trimerization of NPOH, while ZrO2 promoted electrophilic arylation of Qs with NPOH. The resulting products 3 would be useful synthetic intermediates for naturally occurring diosindigo B, biramentaceone and violet-quinone.
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  • The New Method for Introduction of an Allyl Group into the Angular Position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one and Its Application to Chiral Wieland–Miescher Type Compound Synthesis
    Kou Hiroya, Taisuke Takahashi, Katsunori Shimomae, Takao Sakamoto
    2005 Volume 53 Issue 2 Pages 207-213
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.207
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    The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initially formed one. Two diastereomeric Wieland–Miescher type compounds, having the allyl group at the angular position, were synthesized as optically pure forms.
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  • New Cassane-Type Diterpenes of Caesalpinia crista from Myanmar
    Surya Kant Kalauni, Suresh Awale, Yasuhiro Tezuka, Arjun Hari Banskota ...
    2005 Volume 53 Issue 2 Pages 214-218
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.214
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    Seven new cassane-type diterpenes, caesalpinin MF—ML (1—7), and a new norcassane-type diterpene, norcaesalpinin MD (8), have been isolated from the CH2Cl2 extract of seed kernels of Caesalpinia crista from Myanmar, together with sixteen known cassane-type diterpenes, 7-acetoxybonducellpin C, caesaldekarin e, caesalmin C, caesalmin G, 2-acetoxycaesaldekarin e, ζ-caesalpin, caesalpinin D, caesalpinin E, caesalpinin F, caesalpinin H, caesalpinin I, caesalpinin J, caesalpinin K, caesalpinin M, caesalpinin N, and caesalpinin O. The structures of the isolated compounds were elucidated by the use of spectroscopic techniques.
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  • Resveratrol Derivatives from Upuna borneensis
    Tetsuro Ito, Miyuki Furusawa, Toshiyuki Tanaka, Zulfiqar Ali, Ibrahim ...
    2005 Volume 53 Issue 2 Pages 219-224
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.219
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    Four new resveratrol derivatives, upunaphenols B (1), C (4), D (5) (resveratrol tetramer) and E (6, resveratrol dimer with a C6–C1 unit), together with nine known resveratrol oligomers and resveratrol were isolated from an acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structures of new compounds were determined by spectral analysis including 1D and 2D NMR experiments.
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  • New Phenolic Glycosides from the Seeds of Cucurbita moschata
    Kazuo Koike, Wei Li, Lijuan Liu, Emiko Hata, Tamotsu Nikaido
    2005 Volume 53 Issue 2 Pages 225-228
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.225
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    Five new phenolic glycosides, cucurbitosides A—E (1—5), were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as 2-(4-hydroxy)phenylethanol 4-O-(5-O-benzoyl)-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (1), 2-(4-hydroxyphenyl)ethanol 4-O-[5-O-(4-hydroxy)benzoyl]-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (2), 4-hydroxybenzyl alcohol 4-O-(5-O-benzoyl)-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (3), 4-hydroxybenzyl alcohol 4-O-[5-O-(4-hydroxy)benzoyl]-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (4) and 4-hydroxyphenyl 5-O-benzoyl-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.
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Notes
  • A New and Known Cytotoxic Aryltetralin-Type Lignans from Stems of Bursera graveolens
    Tsutomu Nakanishi, Yuka Inatomi, Hiroko Murata, Kaori Shigeta, Naoki I ...
    2005 Volume 53 Issue 2 Pages 229-231
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.229
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    A new 4α-aryltetralin-type lignan called burseranin (1) and a known analogous lignan picropolygamain (2) were isolated along with known triterpenes, lupeol and epi-lupeol from the methanol extract of stems of Bursera graveolens, which showed a remarkable inhibitory activity against human HT1080 fibrosarcoma cells. The whole structure of 1 was established based on combined spectral studies and the absolute structure for 2 was first confirmed by CD spectral evidence. In addition, cytotoxic activities of the stem (methanol) extract and its components are evaluated in this paper.
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  • ent-Pimarane-Type Diterpenoids from Siegesbeckia orientalis L.
    Phan Minh Giang, Phan Tong Son, Hideaki Otsuka
    2005 Volume 53 Issue 2 Pages 232-234
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.232
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    A new ent-pimarane glucoside, named hythiemoside B (4), was isolated from the aerial part of Siegesbecikia orientalis L. (Asteraceae) together with four known ent-pimarane-type diterpenoids: darutigenol (1), darutoside (2), hythiemoside A (3), and ent-(15R),16,19-trihydroxypimar-8(14)-ene 19-O-β-D-glucopyranoside (5). The structure of the new compound was elucidated by spectroscopic analyses and chemical transformation. The NMR data of compounds 1 (1H-) and 5 (1H- and 13C-) were also compiled in this study on the basis of 2D experiments.
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  • Lignan and Neolignan Derivatives from Magnolia denudata
    Jun Li, Makoto Tanaka, Katsuki Kurasawa, Tsuyoshi Ikeda, Toshihiro Noh ...
    2005 Volume 53 Issue 2 Pages 235-237
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.235
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    A new tricyclo[4.2.0.02,8]octane-type neolignan, 6-allyl-7-(3,4-dimethoxyphenyl)- 2,3-dimethoxy-8-methyl-tricyclo[4.2.0.02,8]oct-3-en-5-one, together with 15 known lignan and neolignan derivatives have been isolated from the flower buds of Magnolia denudata DESR. and the structures of these compounds have been elucidated based on the 1H- and 13C-NMR spectra and two-dimensional NMR methods such as HMBC, HMQC, and NOESY.
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  • Eudesmane Sesquiterpenes from the Aquatic Fungus Beltrania rhombica
    Vatcharin Rukachaisirikul, Chutanat Kaewbumrung, Souwalak Phongpaichit ...
    2005 Volume 53 Issue 2 Pages 238-240
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.238
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    From the ethyl acetate extract of the culture broth of Beltrania rhombica, two new eudesmane sesquiterpenes, named rhombidiol (1) and rhombitriol (2), were isolated and characterized along with five enantiomers of known sesquiterpenes: (−)-β-eudesmol, (−)-pterocarpol, (−)-chrysanthemol, (−)-longilobol and (−)-5β-hydroxy-β-eudesmol. Their structures were determined by analysis of 1D and 2D NMR data and comparison of spectral data and physical data with those previously reported.
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  • Acaricidal Daphnane Diterpenoids from Trigonostemon reidioides (KURZ) CRAIB roots
    Noppamas Soonthornchareonnon, Monnun Sakayarojkul, Masahiko Isaka, Van ...
    2005 Volume 53 Issue 2 Pages 241-243
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.241
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    A new daphnane diterpenoid, rediocide F (1), was isolated together with three known compounds, rediocides A (2), C (3) and E (4), from the hexane extract of Trigonostemon reidioides roots by bioassay-guided fractionation for acaricidal activity on Dermatophagoides pteronyssinus, Thai common house dust mite. The structure of rediocide F (1) was established as the demethyl analog of rediocide C (3) on the basis of spectral analysis. Compounds 1—4 exhibited potent activity against D. pteronyssinus with respective LC50 values of 2.53, 0.78, 5.59 and 0.92 μg/cm2.
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  • Bioactive Pyranoxanthones from the Roots of Calophyllum blancoi
    Ya-Ching Shen, Li-Tang Wang, Ashraf Taha Khalil, Lien Chai Chiang, Pei ...
    2005 Volume 53 Issue 2 Pages 244-247
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.244
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    Phytochemical investigation of the roots of Calophyllum blancoi growing in Taiwan resulted in the isolation of three new pyranoxanthones, blancoxanthone (1), acetyl blancoxanthone (2) and 3-hydroxyblancoxanthone (3), in addition to two known pyranoxanthones, pyranojacaeubin (4) and caloxanthone (5). Structural characterization of the isolated compounds was determined by spectral analyses especially 2-D NMR. Biological study of the isolated xanthones revealed that blancoxanthone (1) exhibited significant anti-coronavirus activity.
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  • Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes
    Iwao Okamoto, Wataru Funaki, Sachiyo Nobuchika, Mika Sawamura, Eiichi ...
    2005 Volume 53 Issue 2 Pages 248-252
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.248
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    The combination of electrolysis and the FeIII(PA)3/O2/CH3CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with α-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for α-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.
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  • Prediction of Solubility of Drugs by Conductor-Like Screening Model for Real Solvents
    Hirotaka Ikeda, Kouji Chiba, Atsushi Kanou, Noriaki Hirayama
    2005 Volume 53 Issue 2 Pages 253-255
    Published: 2005
    Released on J-STAGE: February 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.253
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    The solubility of drugs in solvents is fundamentally important for drug development and manufacturing. As the experimental measurements of the solubility are extremely laborious tasks, reliable prediction methods are highly required. We have employed the conductor-like screening model for real solvents (COSMO-RS) in predicting the solubility of drugs and drug-like compounds in various solvent systems. We also evaluated the salt effect on the solubility of caffeine using this method. The present results demonstrated that COSMO-RS has reasonably reproduced the experimental data and have proved that this method is generally available in predicting the solubility of drugs.
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