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Volume 52, Issue 3
Displaying 1-20 of 20 articles from this issue
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Regular Articles
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Huong Doan Thi Mai, Thomas Gaslonde, Sylvie Michel, Michel Koch, Fran& ...2004 Volume 52 Issue 3 Pages 293-297
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSA series of cis-1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine diacid hemiesters and dicarbamates were prepared by acylation of cis-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one. The cytotoxicity of the dicarbamates depended on the steric hindrance of the esterifying groups at positions 1 and 2. Diacid hemiesters displayed significant in vitro cytotoxic activities and induced cell cycle perturbations similar to those obtained with cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1) currently under preclinical development. cis-1-Acetoxy-2-hemiglutaryloxy-1,2-dihydrobenzo[b]acronycine was the most promizing compound of the series, inducing complete inhibition of tumor growth when tested against C38 colon adenocarcinoma implanted in mice.View full abstractDownload PDF (100K) -
Atsuko Fukui, Ryuta Fujii, Yorinobu Yonezawa, Hisakazu Sunada2004 Volume 52 Issue 3 Pages 298-302
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThe release properties of phenylpropanolamine hydrochloride (PPA) from ethylcellulose (EC) matrix granules prepared by an extrusion granulation method were examined. The release process could be divided into two parts; the first and second stages were analyzed by applying square-root time law and cube-root law equations, respectively. The validity of the treatments was confirmed by the fitness of a simulation curve with the measured curve. In the first stage, PPA was released from the gel layer of swollen EC in the matrix granules. In the second stage, the drug existing below the gel layer dissolved and was released through the gel layer. The effect of the binder solution on the release from EC matrix granules was also examined. The binder solutions were prepared from various EC and ethanol (EtOH) concentrations. The media changed from a good solvent to a poor solvent with decreasing EtOH concentration. The matrix structure changed from loose to compact with increasing EC concentration. The preferable EtOH concentration region was observed when the release process was easily predictable. The time and release ratio at the connection point of the simulation curves were also examined to determine the validity of the analysis.View full abstractDownload PDF (105K) -
Anthony Amaechi Attama, Petra Obioma Nnamani, Michael Umale Adikwu, Fl ...2004 Volume 52 Issue 3 Pages 303-306
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThe thermodynamic parameters of the charge transfer complex between chloranilic acid and haloperidol were studied. Haloperidol in pure form and in dosage form was assayed in this study. The method was based on charge transfer complex formation between the drug, which acted as an n-donor, and chloranilic acid, which acted as a π acceptor in a non aqueous solvent. The complex stoichiometry was found to be 1 : 2 (haloperidol : chloranilic acid) with the maximum absorption band at a wavelength of 576 nm. The complex obeyed Beer's law. The thermodynamic parameters investigated included stability constant, molar absorptivity, free energy change, enthalpy, and entropy. The method was successfully applied in the analysis of commercially available haloperidol tablets without interference from its excipients, with good precision and reproducibility, compared with the official assay method (non aqueous titration) described for haloperidol in the compendium.View full abstractDownload PDF (78K) -
Peddaiahgari Vasu Govardhana Reddy, Yarragudi Bathal Reddy Kiran, Cira ...2004 Volume 52 Issue 3 Pages 307-310
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSSeveral new class of phosphorus heterocyclic compounds containing exocyclic P–C link such as 6-(2′-chloroethyl)/(allyl)/(benzyl)-1,2,4,8,10,11-hexachloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides (5—7), 2-(2″-chloroethyl)/(allyl)-6-(1,1-dimethylethyl)-3-cyclohexyl-3,4-dihdro-2H-1,3,2-benzoxazaphosphorin 2-oxides (9, 10), 2-(2″-chloroethyl-2,3-dihydro-3-(4′-bromophenyl)-1H-naphth[1,2-e][1,3,2]-oxazaphosphorin 2-oxide (12), 2-(2″-chloroethyl)/(allyl)-2,3-dihydro-5-benzoyl-1H-1,3,2-benzodiazaphosphole 2-oxides (14, 15), 4-phenyl-2-(2″-chloroethyl)-1H-1,3,3a,5,6-pentaza-2-phosphapentalene 2-oxide (17) and 4-benzyl-2-(2″-chloroethyl)-1H-1,3,3a,5,6-pentaza-2-phospha-pentalene 2-oxide (19) were synthesized by reacting equimolar quantities of corresponding diol (4)/diamines (13, 16, 18), 2-cyclohexylaminomethyl-4-t-butylphenol (8) and 1-(4′-bromoanilinomethyl)-2-naphthol (11), with respective phosponyl dichlorides (1—3) in dry toluene/toluene-tetrahydro-furan/pyridine in the presence of triethylamine at various temperatures. Their structures were established by IR, 1H-, 13C- and 31P-NMR spectral data. The mass spectral data were given for compounds 9, 12 and 15. The title compounds were screened for antibacterial activity against Staphylococcus aureus and Escherichia coli and antifungal activity on Aspergillus niger and Helminthosporium oryzae. Most of the compounds possess significant activity.View full abstractDownload PDF (101K) -
Hiroko F. Kasai, Masayoshi Tsubuki, Yohichiro Matsumoto, Mika Shirao, ...2004 Volume 52 Issue 3 Pages 311-315
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSGas chromatographic separations of the stereoisomers of menthol derivatives, important intermediates in the synthesis of physiologically active natural products, were carried out on several substituted β-cyclodextrin (CD) columns, including per-O-methyl-β-cyclodextrin (PME-β-CD), heptakis(2,3-di-O-acetyl-6-tert-butyldimethylsilyl)-β-CD (DIAC-6-TBDS-β-CD), and heptakis(2,3-di-O-methyl-6-tert-butyldimethylsilyl)-β-CD (DIME-6-TBDS-β-CD) as chiral stationary phases (CSPs). With the DIME-6-TBDS-β-CD column, a separation of the Z- and E-isomers of methylidenementhol was accomplished; no separation was achieved with the other columns. The stereoisomers of methylidenementhol and the corresponding tert-butyldimethylsilyl (TBS) ether were separated on both the β-CD and the heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TME-β-CD) columns by high-performance liquid chromatography (HPLC) with a mobile phase involving acetonitrile and H2O. For the separation of the Z- and E-isomers of methylidenementhol, the TME-β-CD column was superior. In contrast, the β-CD column was preferable in the case of the corresponding TBS ether.View full abstractDownload PDF (118K) -
Jaskiran Kaur, Narendra Nath Ghosh, Ramesh Chandra2004 Volume 52 Issue 3 Pages 316-321
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSA new series of N-substituted bis-(tetrahydropapaverine) ring systems have been synthesised in expectation of better antispasmodic activity in comparison with papaverine. The synthesis of the targeted heterocycles is described along with a discussion of their structure activity relationship. The general synthetic methods of bis-(tetrahydropapaverine) analogues involve tetrahydropapaverine, various piperazines, diisocyanates and diisothiocyanates as starting materials. Pharmacological evaluation involves the in vitro antispasmodic activity on a freshly removed guinea pig ileum using a force displacement transducer amplifier connected to a physiograph. Among the analogues synthesized in the present study, N,N′-bis-[2-carbamoyl-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolinyl]piperazine (22), was found to be the most potent muscle relaxant (IC50: 0.31 μM).View full abstractDownload PDF (147K) -
Shinji Ohmori, Yasuo Ohno, Tadashi Makino, Toshio Kashihara2004 Volume 52 Issue 3 Pages 322-328
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThe purpose of this study was to improve the impact toughness of sugar-coated tablets manufactured by a dusting method. The effects of sugar-coating formulations, which were the sugar-coating suspension formulations and the dusting powder formulations, on impact toughness of sugar-coated tablets were investigated. Impact toughness of sugar-coated tablets was measured by the friability test. We found that the dusting powder formulation was a control factor in impact toughness of sugar-coated tablets manufactured by the dusting method. The dusting method using dusting powder containing 20% microcrystalline cellulose (MCC, Avicel PH-F20) was a useful method for improvement of the impact toughness of sugar-coated tablets. The mechanism of improvement of impact toughness was that MCC in the subcoating layer resulted in a tight bond between the subcoating layer and the smoothing layer and prevented separation of the two layers on impact, because MCC improved the wettability of the subcoating layer, increased the surface roughness of the subcoating layer, and played the role of a binder between the two layers. We confirmed that the MCC between the subcoating layer and the smoothing layer acts to prevent separation of the two layers by impact. We demonstrated that MCC is a suitable material for sugar-coating in order to improve the impact toughness of sugar-coated tablets.View full abstractDownload PDF (576K) -
Shinji Ohmori, Yasuo Ohno, Tadashi Makino, Toshio Kashihara2004 Volume 52 Issue 3 Pages 329-334
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThe purpose of this study was to clarify the effect of moisture on the impact toughness of sugar-coated tablets manufactured by the dusting method. We demonstrated that moisture plays an important role in the impact toughness of sugar-coated tablets. Moisturizing the sugar-coating layer resulted in enhancement of impact toughness of sugar-coated tablets, while reducing moisture in the sugar-coating layer resulted in weakening of the impact toughness. This was due to the characteristics of sucrose, the main ingredient of the sugar-coating layer, which is a soft and non-fragile material at high moisture levels, but hard and fragile at low moisture levels. We also demonstrated that friability as an indicator of impact toughness changed with time, and friability should be measured at 14 d after manufacture. This is due to moisture movement from outer sugar-coating layer into the inner sugar-coated tablets. Incorporating microcrystalline cellulose (MCC) in the subcoating layer resulted in sugar-coating layers with high resistance against impact even though moisture content of sugar-coated tablets was low. We confirmed the high impact toughness of the sugar-coated tablets with MCC whose moisture content was low from the results of both free fall and friability tests. We suggest that the dusting method using dusting powder containing MCC is a useful method for the production of sugar-coated tablets containing moisture sensitive drugs.View full abstractDownload PDF (92K) -
Kazuhiro Nojima, Yasuko Yamaashi2004 Volume 52 Issue 3 Pages 335-338
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSUpon exposure to sunlight, or to artificial light at wavelengths longer than 290 nm, sulfur dioxide in air underwent oxidation to give sulfur trioxide in the presence of air pollutants such as biacetyl (2,3-butanedione), benzaldehyde and nitrogen dioxide, but not in their absence. Only nitrogen dioxide completely oxidized sulfur dioxide to sulfur trioxide.View full abstractDownload PDF (91K) -
Yasushi Sasai, Yukinori Yamauchi, Shin-ichi Kondo, Masayuki Kuzuya2004 Volume 52 Issue 3 Pages 339-344
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSMechanically induced free radical (mechanoradical) formation of several substituted celluloses such as carboxylmethyl cellulose, chitin, and chitosan was studied based on electron-spin resonance (ESR) in comparison with those of plasma-induced radicals. Room temperature ESR spectra had multicomponent spectra and were different in pattern from each other. The mechanoradical concentration gradually decreased after reaching the maximum value in each substituted polysaccharide, accompanied by a decrease in molecular weight in the course of vibratory milling. One of the most intriguing facts is that the component radicals are all glucose-based radicals as in the case of plasma irradiation, although it is known that mechanoradicals are formed by 1,4-glucosidic bond cleavage of polysaccharides.View full abstractDownload PDF (198K) -
Pei-Lin Wu, Fu-Wen Lin, Tian-Shung Wu, Chang-Sheng Kuoh, Kuo-Hsiung Le ...2004 Volume 52 Issue 3 Pages 345-349
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThree new compounds: begonanline (1), nantoamide (2) and methyl (S)-glycerate (3) as well as forty-four known compounds have been isolated and characterized from the rhizomes of Begonia nantoensis. The structures of these compounds were determined by spectral analyses and/or X-ray crystallography. Among them, cucurbitacin B (4), dihydrocucurbitacin B (5), cucurbitacin E (6), dihydrocucurbitacin E (7), cucurbitacin I (8), and (−)-auranamide (9) showed cytotoxicity against four human cancer cell lines. 3β,22α-Dihydroxyolean-12-en-29-oic acid (10), indole-3-carboxylic acid (11), 5,7-dihydroxychromone (12), and (−)-catechin (13) demonstrated significant activity against HIV replication in H9 lymphocyte cells.View full abstractDownload PDF (95K)
Notes
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Kotaro Iida, Youhei Hayakawa, Hirokazu Okamoto, Kazumi Danjo, Hans Lue ...2004 Volume 52 Issue 3 Pages 350-353
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThe effect of the surface layering time of lactose carrier particles on the dry powder inhalation properties of salbutamol sulfate was investigated. Lactose carrier particles were layered with vegetable magnesium stearate by physical mixing. In the present study, drug/carrier powder mixtures were designed consisting of micronized salbutamol sulfate and lactose carriers with various particle surface conditions prepared by surface layering. These powder mixtures were aerosolized by a Jethaler®, and the in vitro deposition properties of salbutamol sulfate were evaluated by a twin impinger. Compared with the powder mixed with unlayered lactose carrier, the in vitro inhalation properties of the powder mixture prepared using the surface layering lactose carrier were significantly different, showing that the in vitro inhalation properties of the drug/carrier powder mixtures were improved. In vitro deposition properties (RP) increased with surface layering time. Using this surface layering system would thus be valuable for increasing the inhalation properties of dry powder inhalation.View full abstractDownload PDF (203K) -
Shigenobu Arihara, Akemi Umeyama, Shinya Bando, Shinji Imoto, Mikako O ...2004 Volume 52 Issue 3 Pages 354-358
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSThree new diterpenes, sugikurojins A—C (1—3) were isolated from the black heartwood of Cryptomeria japonica. The structure of sugikurojin A was deduced to be 19-hydroxy-6,7-dehydroferruginol on the basis of extensive NMR experiments. Sugikurojin B was a dimer of 6,7-dihydroxyferruginol and 6,7-dehydroferruginol with a 6-O-11′ linkage. Sugikurojin C was a dimeric ferruginol with 6-O-7′ and 7-O-6′ linkages. Also obtained in this investigation were the known compounds formosaninol (4), 15 sesquiterpenes (5—19), 16 diterpenes (20—35), three phenylpropanoids (36—38), and a phenolic compound (39).View full abstractDownload PDF (96K) -
Hiromitsu Takayama, Hayato Ishikawa, Mariko Kitajima, Norio Aimi, Baba ...2004 Volume 52 Issue 3 Pages 359-361
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSA new yohimbine-type indole alkaloid (1) was isolated from the stem bark of Mitragyna africanus (WILLD.) collected in Nigeria, along with known seven Corynanthe-type oxindole alkaloids, two secoiridoids, three lignans, and a quinovic acid derivative. Their structures were elucidated by spectroscopic analyses.View full abstractDownload PDF (68K) -
Naoko Negi, Yu Jinguji, Kaori Ushijima, Shinobu Ikeda, Yuko Takemura, ...2004 Volume 52 Issue 3 Pages 362-364
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSTwo new acridone dimers, glycobismines-F (1) and -G (2), were isolated from the roots of Glycosmis citrifolia collected in Taiwan. The structures of the new compounds were determined based on spectral analysis.View full abstractDownload PDF (80K) -
Hideharu Uchiki, Hiroyuki Miyachi2004 Volume 52 Issue 3 Pages 365-367
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSIn order to investigate the reason why phenylpropanoic acid derivative (KCL), a potent, human peroxisome proliferator-activated receptor (PPAR) α-selective agonist, shows this selectivity, we analyzed the binding modes of KCL and a related compound to the ligand-binding domain of human PPARα and rat PPARα by means of computer-aided molecular modeling. We concluded that the characteristic specificity of KCL is due to a specific hydrophobic contact between the hydrophobic tail part (the 4-trifluoromethyl group) and the key amino acid Ile272 located on the helix three region of the human PPARα ligand binding domain. We propose a possible binding mode of KCL with the ligand-binding domain of human PPARα. This binding model should offer important insights for further structural design of subtype-selective PPARα agonists for the treatment of altered metabolic homeostasis, such as dyslipidemia, obesity, and diabetes.View full abstractDownload PDF (242K) -
Satomi Nakatani, Yukinori Yamamoto, Masahiko Hayashi, Kanki Komiyama, ...2004 Volume 52 Issue 3 Pages 368-370
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSCycloanthranilylproline (1) and its derivatives (2—4) were isolated from field-collected fruit-bodies of a myxomycete Fuligo candida and their structures were elucidated by spectral data. Compound 4, which was contained in the water-soluble fraction of the extract of this myxomycete, was unstable and quite susceptible to decarboxylation to yield compound 2, which was a major constituent of the EtOAc-soluble fraction of this extract.View full abstractDownload PDF (64K) -
Genta Kakiyama, Takashi Iida, Takaaki Goto, Nariyasu Mano, Junichi Got ...2004 Volume 52 Issue 3 Pages 371-374
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSA method for the synthesis of 3α,7α,14α-trihydroxy-5β-cholan-24-oic acid which is a possible candidate of bile acid metabolite in vertebrates was developed. The principal reactions involved were 1) stereoselective remote-hydroxylation of methyl ursodeoxycholate diacetate with dimethyldioxirane, 2) site-selective protection at C-3 by tert-butyldimethylsilylation of the resulting 3α,7α,14α-trihydroxy ester, 3) oxidation of the diol with pyridinium dichromate adsorbed on activated alumina, 4) stereoselective reduction of the 7-ketone with zinc borohydride, and 5) cleavage of the protecting group at C-3 with p-toluenesulfonic acid. A facile elimination of the 14α-hydroxy group under an acidic or neutral condition is also described. The synthetic reference compound is now available for comparison with unidentified biliary bile acids detected in vertebrate bile.View full abstractDownload PDF (85K)
Communications to the Editor
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Yong Li, Xifeng Li, Se-Kwon Kim, Jung Sook Kang, Hong Dae Choi, Jung R ...2004 Volume 52 Issue 3 Pages 375-376
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSA new diketopiperazine alkaloid, golmaenone (1) and related alkaloids, neoechinulin A (2) and L-alanyl-L-tryptophan anhydride (3), have been isolated from the culture broth of the marine-derived fungus Aspergillus sp. The structure and absolute stereochemistry of the new compound (1) was assigned by spectroscopic methods and the advanced Marfey's method. Compounds 1 and 2 exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 values of 20 and 24 μM, respectively, which are similar to the positive control, ascorbic acid (IC50, 20 μM). Compounds 1 and 2 also showed an ultraviolet-A (UV-A) (320—390 nm) protecting activity with ED50 values of 90 and 170 μM, respectively, which are more active than oxybenzone (ED50, 350 μM) currently being used as sunscreen.View full abstractDownload PDF (56K) -
Naganori Numao, Hisashi Fujii, Yoshiyuki Fukazawa, Nobutaka Hanagata, ...2004 Volume 52 Issue 3 Pages 377-379
Published: 2004
Released on J-STAGE: March 01, 2004
JOURNAL FREE ACCESSIn the sequence Fourier analysis (SFA) of specific interactions such as those between fibroblast growth factors (FGFs)/FGF receptors (FGFRs), bone morphogenetic proteins (BMPs)/BMP receptors (BMPRs), or tumor repressor protein p53/mouse double minute 2 homolog (MDM2), the characteristic frequency peak(s) could be observed with the hydrophobic scale for 20 amino acids as well as 4 nucleotides as the physicochemical parameter, but not successfully with the absolute electronegativity scale. This result implies that these two independent scales should be appropriately selected in various specific ligand–protein interactions, though the critical difference has to be determined.View full abstractDownload PDF (129K)
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