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Volume 53, Issue 4
Displaying 1-24 of 24 articles from this issue
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Regular Articles
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Satoru Watano, Takumi Okamoto, Yoshinobu Sato, Yoshifumi Osako2005 Volume 53 Issue 4 Pages 351-354
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSScale-up of wet granulation in a vertical high shear mixer was conducted. Pharmaceutical excipient powders composed of lactose, cornstarch and micro-crystallinecellulose, and hydroxypropylcellulose as a binder were mixed together and then granulated with purified water under various operating conditions and vessel scales. A novel internal stress measurement system was developed and stress of normal and tangential directions that granules received from the agitator blade during the granulation was continuously measured. The results indicated that granules received stress mainly from the tangential direction, which also showed the largest value near at the vessel wall. The effects of the agitator tip speed and the centrifugal acceleration on the measured stress was investigated. It was found that the tip speed of the agitator blade could be the main factor for the granule growth. The physical properties such as strength, size distribution and compressibility of granules prepared by changing the operating conditions and the vessel scales were evaluated and the scale-up characteristics of high shear granulation were investigated experimentally. The results showed that these physical properties had linear correlations with the tip speed. It was finally concluded that the scale-up of high shear granulation could be well conducted by means of the tip speed of the agitator blade.View full abstractDownload PDF (217K) -
Okiko Miyata, Hiroshi Asai, Takeaki Naito2005 Volume 53 Issue 4 Pages 355-360
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe imino 1,2-Wittig rearrangement of hydroximates containing a furan ring provides a novel method for the synthesis of β-hydroxy-α-amino acids. Upon treatment with LDA, hydroximates smoothly underwent the rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into both cis- and trans-oxazolidinones with high stereoselectivity. The cis- and trans-oxazolidinones were stereoselectively converted into erythro- and threo-β-hydroxyphenylalanines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.View full abstractDownload PDF (197K) -
Hideki Kanho, Sayaka Yaoya, Nobuo Kawahara, Takahisa Nakane, Yoichi Ta ...2005 Volume 53 Issue 4 Pages 361-365
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3,4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalcohol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyranosylvanillylalcohol was obtained as the main product. In the case of 3,4-dimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.View full abstractDownload PDF (206K) -
Yue Wang, Nobuo Okabe2005 Volume 53 Issue 4 Pages 366-373
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe crystal structures of the series of four ternary complexes, [Pd(phen)(2,6-PDCA)]·4H2O (1) (phen=1,10-phenanthroline; 2,6-PDCA=2,6-pyridinedicarboxylic acid), [Pd(bpy)(2,3-PDCA)]·3H2O (2) (bpy=2,2′-bipyridineand; 2,3-PDCA=2,3-pyridinedicarboxylic acid) and [Pd(phen)(PHT)]·2.5H2O (3) (PHT=o-phthalic acid ) and [Pd(bpy)(PHT)]·1.5H2O (4), are determined and the coordination modes of palladium(II) ternary complexes are characterized. All complexes take the mononuclear Pd(II) complexes, in which central Pd(II) atom of each complex has a similar distorted square-planar four coordination geometry. In all complexes, the aromatic heterocyclic compounds, phen and bpy, behave as a bidentate N, N′ ligand. In the complex 1 and 2, 2,6-PDCA and 2,3-PDCA behave as a bidentate N, O ligand, and in complex 3 and 4, PHT behaves as a bidentate O, O′ ligand.View full abstractDownload PDF (1387K) -
Hideji Tanaka, Xiangli Liu, Daichi Kawabata, Hiroshi Chuman, Chisako Y ...2005 Volume 53 Issue 4 Pages 374-377
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe chloroform/water distribution coefficients (KD) of sixteen diazine compounds were determined by a stepwise flow ratiometry. An aqueous solution of analyte was delivered and merged with chloroform. The flow rate ratio of both the phases was varied stepwise under a constant total (chloroform+aqueous) flow rate. The analyte was extracted to chloroform while both the phases, which were segmented by each other, were passing through an extraction coil. The segmented stream was then led to a UV/Vis detector directly without phase-separation. The absorbance of the chloroform and aqueous phases (Ao and Aa, respectively) was each measured at the maximum absorption wavelength of the analyte. The plots of A−1 against Rf, (ARf)−1 against Rf−1, and ARf against A gave straight lines, where A was Ao, Aa or the sum of them (AS). The KD of the analyte was calculated from the slopes and intercepts of the plots. The log KD values obtained for the analytes (−0.5—1.4) were agreed well with the values measured by a shake-flask method. The present method is simple, rapid (5 min/determination) and applicable to the volatile compounds with reasonable precision (standard deviation of log KD<0.07).View full abstractDownload PDF (149K) -
Viqar Uddin Ahmad, Afsar Khan, Umar Farooq, Farzana Kousar, Saleha Sul ...2005 Volume 53 Issue 4 Pages 378-381
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThree new tricyclic cis-clerodane type diterpenoids trivially named as limbatolide A (1), limbatolide B (2) and limbatolide C (3) have been isolated from the roots of Otostegia limbata along with two known compounds; oleanic acid and β-sitosterol. The structure elucidation of the new compounds was based primarily on two-dimensional (2D) NMR techniques. Compounds 1—3 displayed inhibitory potential in a concentration-dependent manner against acetylcholinesterase (AChE; EC 3.1.1.7) and butyrylcholinesterase (BChE; EC 3.1.1.8) enzymes, respectively.View full abstractDownload PDF (103K) -
Fumiaki Kisa, Koji Yamada, Masafumi Kaneko, Masanori Inagaki, Ryuichi ...2005 Volume 53 Issue 4 Pages 382-386
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSFive glucocerebroside molecular species, SJC-1-SJC-5, have been isolated from the less polar lipid fraction of a chloroform/methanol extract of the sea cucumber Stichopus japonicus. The structures of these glucocerebroside molecular species were determined on the basis of chemical and spectroscopic evidence. SJC-1, SJC-2, and SJC-3 are typical sphingosine- and phytosphingosine-type glucocerebroside molecular species with nonhydroxylated and hydroxylated fatty acyl moieties. SJC-4 and SJC-5 are also sphingosine-type glucocerebroside molecular species with hydroxylated fatty acyl moieties, although they are new glucocerebroside molecular species with unique sphingosine bases.View full abstractDownload PDF (200K) -
Hisashi Matsuda, Toshio Morikawa, Teruki Ohgushi, Tomoko Ishiwada, Nor ...2005 Volume 53 Issue 4 Pages 387-392
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe methanolic extract from the flowers of Angelica furcijuga KITAGAWA was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. From the methanolic extract, two new glycosides, hyuganosides IV and V, were isolated together with 28 known constituents. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. Furthermore, the inhibitory effects of 11 coumarin constituents on nitric oxide production were examined. Among them, 3′-angeloyl-cis-khellactone (IC50=82 μM), (S)-(−)-oxypeucedanin (57 μM), imperatorin (60 μM), isoepoxypteryxin (53 μM), and isopteryxin (8.8 μM) showed inhibitory activity.View full abstractDownload PDF (226K) -
Teppei Kumemura, Tominari Choshi, Aki Hirata, Mitsuko Sera, Yohhei Tak ...2005 Volume 53 Issue 4 Pages 393-397
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSA total synthesis of a new furo[3,2-h]isoquinoline alkaloid TMC120-B (2), isolated from Aspergillus ustus together with two related compounds, has been completed in sixteen steps. The key step is the synthesis of the appropriate 3,7,8-trisubstituted isoquinoline framework (23) based on a thermal electrocyclic reaction of the 1-aza 6π-electron system involving the benzene double bond. In addition, the microwave assisted electrocyclic reaction of this system was newly performed.View full abstractDownload PDF (173K) -
Chisako Yamagami, Akira Hamasaki, Yukiko Kumagai, Tetsuhiro Moritoki, ...2005 Volume 53 Issue 4 Pages 398-401
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSWe recently proposed a new hydrogen-accepting scale, SHA, on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, the same approach was applied to a series of compounds with a common hydrogen-donor group. Thus the SHA values for monosubstituted phenols were calculated and used for correlating their log Poct values (Poct: 1-octanol/water partition coefficient) with log PCL (PCL: chloroform/water partition coefficient) and log PE (PE: butyl ether/water partition coefficient). It was demonstrated that the SHA parameter works effectively, providing excellent correlations whose physicochemical meanings are well rationalized in terms of hydrogen-bonding characteristics of the substituents.View full abstractDownload PDF (91K) -
Isao Kinoyama, Nobuaki Taniguchi, Eiji Kawaminami, Eisuke Nozawa, Hiro ...2005 Volume 53 Issue 4 Pages 402-409
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSA novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this series trans-N-4-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2,4-difluorophenyl)-2,5-dimethylpiperazine-1-carboxamide (18g, YM-175735) exhibited the most potent antiandrogenic activity. Compared to bicalutamide, YM-175735 is an approximately 4-fold stronger AR antagonist and has slightly increased antiandrogenic activity, suggesting that YM-175735 may be useful in the treatment of prostate cancer.View full abstractDownload PDF (240K) -
Seiji Miwatashi, Yasuyoshi Arikawa, Ken-ichi Naruo, Keiko Igaki, Yasum ...2005 Volume 53 Issue 4 Pages 410-418
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSA novel series of 4-phenyl-5-pyridyl-1,3-thiazole analogues possessing potent in vitro inhibitory activity against p38 mitogen-activated protein kinase and the release of tumor necrosis factor-α (TNF-α) from human monocytic THP-1 cells stimulated by lipopolysaccharide has been identified. Subsequent structure–activity relationship (SAR) studies and optimization for absorption, distribution, metabolism, and elimination (ADME) profiles led to the identification of compounds 7g and 10b as orally active lead candidates that block the in vivo production of proinflammatory cytokine (TNF-α). In pharmacokinetic studies, compound 10b showed good oral administration in mice and demonstrated significant in vivo anti-inflammatory activity in an anti-collagen monoclonal antibody-induced arthritis mouse model (minimum effective dose (MED)=30 mg/kg). Further elucidation of this class of compounds may provide novel anti-inflammatory agents, such as anti-rheumatoid arthritis drugs.View full abstractDownload PDF (334K)
Notes
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Jun Cheng, Yu-Ying Zhao, Bin Wang, Liang Qiao, Hong Liang2005 Volume 53 Issue 4 Pages 419-421
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSFrom the stems of Millettia nitida var. hirsutissima, three new isoflavone glycosides, formononetin 7-O-β-D-(6″-ethylmalonyl)-glucopyranoside (1, hirsutissimiside A), 5-O-methyl genistein 7-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (3, hirsutissimiside B), retusin 7,8-di-O-β-D-glucopyranoside (4, hirsutissimiside C) and two known isoflavone glycosides (2) and (5) have been isolated. The structures of the compounds were determined by spectroscopic and chemical means.View full abstractDownload PDF (99K) -
Anamai Thetkathuek, Matthew Keifer, Wijitr Fungladda, Jaranit Kaewkung ...2005 Volume 53 Issue 4 Pages 422-424
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSWe sought to investigate the early biological effects of chlorpyrifos among 53 Thai fruit farm workers by measuring the plasma cholinesterase (PChE) and red blood cell cholinesterase (AChE) activities, a biomarker of organophosphate (OPs) pesticide during one fruit crop. The ChE activity (Vm/Km) was spectrophotometrically analyzed before and after exposing to chlorpyrifos. The Vm/Km values of both non-spraying and spraying seasons are found as normal distribution pattern. The median PChE and AChE activities among farm workers in the non-spraying season were 2.3×10−3 s−1 and 7.26×10−5 s−1, respectively. The median PChE and AChE activities of the farm workers in the spraying season were 2.02×10−3 s−1 and 5.95×10−5 s−1, respectively. The mean Vm/Km values of PChE shifted left (t-test, p=0.013), indicating a decrease in PChE activity in the farm workers exposed to chlorpyrifos. However, the Vm/Km values of AChE in nonspraying season and in the spraying season were not different (t-test, p=0.246). We propose that PChE activity can be used as a biomarker for monitoring early toxicity induced by chlorpyrifos insecticide.View full abstractDownload PDF (259K) -
Shuji Yasuike, Yoshihito Kishi, Shin-ichiro Kawara, Jyoji Kurita2005 Volume 53 Issue 4 Pages 425-427
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSBenzoins are simply oxidized to benzils in excellent yields with a catalytic amount of triarylstibanes under an aerobic condition. This catalytic oxidation is heteroatom-specific in the antimony compound and no reaction take place with other group 15 reagents such as triphenylphosphane, -arsane and -bismuthane. The reaction should involve an oxidation–reduction cycle between stibane Sb(III) and stiborane Sb(V) under air.View full abstractDownload PDF (92K) -
Phan Van Kiem, Chau Van Minh, Hoang Thanh Huong, Jung Joon Lee, Young ...2005 Volume 53 Issue 4 Pages 428-430
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSA new cassane diterpenoid, caesaldecan, was isolated from Caesalpinia decapetala with eight known compounds, spathulenol, 4,5-epoxy-8(14)-caryophyllene, squalene, lupeol, trans-resveratrol, quercetin, astragalin, and stigmasterol. The 1H- and 13C-NMR spectra of the new compound were completely assigned by using a combination of 2D NMR techniques, namely, 1H–1H COSY, HMQC, HMBC, and ROESY.View full abstractDownload PDF (95K) -
Kotaro Iida, Hiroaki Todo, Hirokazu Okamoto, Kazumi Danjo, Hans Leuenb ...2005 Volume 53 Issue 4 Pages 431-434
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSAn attempt was made to produce carrier particles for dry powder inhalation with lactose carrier particles surface-coated using a Wurster fluidized bed. The lactose carrier particles were coated with lactose aqueous solution containing hydroxypropyl methyl cellulose (HPMC) as a binder using a Wurster coating apparatus. Drug/carrier powder mixtures were prepared consisting of micronized salbutamol sulfate and lactose carriers under various particle surface conditions. These powder mixtures were aerosolized by a Jethaler®, and the in vitro deposition properties of salbutamol sulfate were evaluated by a twin impinger. The in vitro inhalation properties of the powder mixture prepared using the coated lactose carrier differed significantly compared with those of the powder mixture prepared using the uncoated lactose carrier, indicating improvements in in vitro inhalation properties of sulbutamol sulfate. In vitro inhalation properties increased with the surface coating time. This surface coating system would thus be valuable for increasing the in vitro inhalation properties of dry powder inhalation with lactose carrier particles.View full abstractDownload PDF (430K) -
Madeleine Blanc, Maud Martin, Sabrina Okombi, Ahcène Boumendjel2005 Volume 53 Issue 4 Pages 435-436
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSThe synthesis of conveniently substituted 2′-amino-α,β-epoxychalcones is described. They were obtained through Darzens condensation of 2′-amino-3′,5′-dimethoxy-α-chloroacetophenone with benzaldehydes. The latter can undergo different cyclization possibilities and afford a variety of flavonoid analogs with biological potential.View full abstractDownload PDF (85K) -
Yufu Sagara, Morihiro Mitsuya, Minaho Uchiyama, Yoshio Ogino, Toshifum ...2005 Volume 53 Issue 4 Pages 437-440
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSSynthesis and structure–activity relationship of a new class of muscarinic M3 selective antagonists were described. In the course of searching for a muscarinic M3 antagonist with a structure distinct from those of the 2-(4,4-difluorocyclopentyl)-2-phenylacetamide derivatives, we identified a thiazole-4-carboxamide derivative (1) as a lead compound in our in-house chemical collection. Since this compound (1) showed relatively low binding affinity (Ki=140 nM) for M3 receptors in the human binding assays, we tried to improve its potency and selectivity for M3 over M1 and M2 receptors by derivatization of 1 through a combinatorial approach. A solution-phase parallel synthesis effectively contributed to the optimization of each segment of 1. Thus, we have identified a cyclooctenylmethyl derivative (3e) and a cyclononenylmethyl derivative (3f) as representative M3 selective antagonists in this class.View full abstractDownload PDF (200K) -
Mohammad Abu Hena Mostofa Kamal, Tomohiro Nabekura, Shuji Kitagawa2005 Volume 53 Issue 4 Pages 441-443
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSpH-dependency of skin permeability to salicylic acid was examined in excised guinea pig dorsal skin. Permeation followed the pH-partition theory at acidic pH. However, above pH 5.0 the observed permeability coefficients were larger than the estimated values obtained from the ratio of the undissociated forms. These findings are quite different from those obtained using the same drug and a silicone rubber membrane, in which permeability coefficients were consistent with the pH-partition theory. The findings suggested that permeation of salicylate as anions occurred at a neutral skin pH. The permeability coefficient of the ionized form was estimated to be about 1.6% of the nonionized form. We also examined the skin permeability of salicylate and its five 5-substituents and two 3-substituents at pH 7.4. We investigated the relationship between their permeability coefficients and the physico-chemical properties of the substituents. Multi regression analysis on the permeability coefficients showed a parabolic relationship between the values of the hydrophobic parameter (π) and the logarithms of the permeability coefficients. These findings suggested that the ionic permeation pathway of salicylate derivatives is controlled by hydrophobic as well as hydrophilic properties.View full abstractDownload PDF (74K) -
Takashi Masuko, Koichi Metori, Yasuo Kizawa, Tadashi Kusama, Muneharu ...2005 Volume 53 Issue 4 Pages 444-447
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSPolyamines, especially spermine, inhibit N-methyl-D-aspartate (NMDA) receptors as open channel blockers. Two types of water-soluble NMDA receptor antagonist, ACCn (1) and TGCn (2), with a 1,4,7,10-tetraazacyclododecane cyclic polyamine group, were synthesized and the effects of both compounds on NMDA receptors were studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. These compounds inhibited macroscopic currents in both NR1/NR2A and NR1/NR2B receptor subtypes in oocytes voltage-clamped at −70 mV. Inhibition by the compounds of NR1/NR2A receptors were more prominent than that of NR1/NR2B receptors. The inhibitory effects of ACCn (1) on both NMDA receptors were more potent than those of TGCn (2).View full abstractDownload PDF (181K) -
Hiroyuki Koshio, Tsukasa Ishihara, Hiroyoshi Yamada, Fukushi Hirayama, ...2005 Volume 53 Issue 4 Pages 448-450
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSA practical and cost-effective procedure has been developed for the synthesis of 7-methyl-2-naphthalenecarbonitrile, the precursor of the anticoagulant agents YM-60828 or YM-96765. This new route generates the key intermediate in only two steps from readily available 3-cyanopropionaldehyde dimethyl acetal and m-tolualdehyde, without requiring chromatographic purification. The synthesis involves condensation of the cyano derivative with the aldehyde and subsequent cyclodehydration.View full abstractDownload PDF (74K)
Communications to the Editor
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Eriko Ueda, Yutaka Yoshikawa, Hiromu Sakurai, Yoshitane Kojima, Naemi ...2005 Volume 53 Issue 4 Pages 451-452
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSWe found alpha-glucosidase inhibitory effect of Zn(II) complex with 6-methyl-2-picolinmethylamide (6mpa-ma) which showed the highest blood glucose lowering effect in Zn(II) complexes with picolinamide derivatives in KK-Ay mice. The Zn(II) complex showed strong alpha-glucosidase inhibitory activity greater by about eighty times (substrate: maltose) and forty times (substrate: sucrose) compared with acarbose.View full abstractDownload PDF (184K) -
Xifeng Li, Min Kyung Kim, Uk Lee, Se-Kwon Kim, Jung Sook Kang, Hong Da ...2005 Volume 53 Issue 4 Pages 453-455
Published: 2005
Released on J-STAGE: April 01, 2005
JOURNAL FREE ACCESSNew 3-amino-5-ethenylcyclopentenones, myrothenones A (4) and B (5), were isolated together with known 6-n-pentyl-α-pyrone (1), trichodenone A (2), and cyclonerodiol (3) from the marine algicolous fungus of genus of Myrothecium. The structure and absolute stereochemistry of the new compounds were established by spectral interpretation and X-ray analysis. Compounds 1 and 4 exhibited a tyrosinase inhibitory activity with IC50 value of 0.8 and 6.6 μM, respectively, which are more active than kojic acid (IC50, 7.7 μM) currently being used as a functional personal-care compound.View full abstractDownload PDF (94K)
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