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Volume 60, Issue 4
Displaying 1-20 of 20 articles from this issue
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Review
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Masami KuriyamaArticle type: Review
2012 Volume 60 Issue 4 Pages 419-428
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSEffective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.View full abstractDownload PDF (1402K)
Regular Articles
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Mio Tange, Miyako Yoshida, Yuka Nakai, Takahiro UchidaArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 429-434
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe purpose of this study was to compare the compatibility of ROCEPHINE® Intravenous, the original manufacturer’s ceftriaxone sodium preparation for injection, and seven generic versions thereof, with various calcium chloride injection 2%. The influence of calcium ion concentration, storage time and shaking strength on the appearance and quantity of insoluble microparticles in mixed solutions was examined using a light obscuration particle counter. In all products, the observed number of insoluble microparticles was proportional to the calcium ion concentration, storage time and shaking strength after the addition of calcium chloride solution. In several of the generic products, the number of insoluble microparticles was significantly higher than those of the original product, while in others it was lower. We evaluated the quality of the original and 7 generic preparations, measured the content of impurity and pH of the various ceftriaxone solutions, as impurity content and pH of solution are possible factor affecting compatibility. Three impurities were found in all products. The impurity content of several generic products, as estimated from their peak area on high performance liquid chromatography (HPLC), was significantly lower than that of the original product. pH of solution was difference between products. Although it was difficult that impurity and pH of solution verify critical factor affecting compatibility. The results show that there are differences in the appearance of insoluble microparticles between the original product and seven generic products, when calcium chloride injection 2% solution is added to the product.View full abstractDownload PDF (743K) -
Yue Wang, Qiaomei Jin, Guowu Lin, Taotao Yang, Zhanwei Wang, Yi Lu, Yi ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 435-441
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSSeries of 3-substituted of 6-aminosulfonyl-β-carbolines were designed and synthesized. In addition, the binding mode of these β-carboline derivatives with cyclin-dependent kinase 2 (CDK2) was studied by means of fluorescence measurements and molecular docking calculation. The results showed that replacement of 3-cyclohexylmethoxy group will increase the hydrophobic binding interaction with the deep hydrophobic pocket of CDK2 correlate to the higher binding intensity.View full abstractDownload PDF (1154K) -
Yutaka Inoue, Hironori Shimazaki, Isamu Murata, Masayuki Kimura, Ikuo ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 442-448
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe purpose of the present study was to evaluate the taste and smell of Tulobuterol Dry Syrup (TB-DS) in its original form (formulation A) and generic form (formulations B and C) by means of gustatory sensation tests and taste and smell sensors. In addition, the physicochemical properties of the syrups in a solid state were compared. Evaluation of sweetness with a powdered sample revealed significant differences between formulation A and formulation B and between formulation B and formulation C. In contrast, the results of principal component analysis (PCA) with a taste sensor revealed differences in principal component 1 (PC 1) among formulations A, B, and C. Smell sensor measurement of powdered samples revealed differences in products in terms of only PC 1, but these results were not related to the results of gustatory sensation testing with a smell sensor. Measurement of particle size distribution and scanning electron microscopy revealed differences in the particle diameter and particle surface shape for each product. Formulation B had the strongest absorption in the near-infrared spectrum, followed by formulation A and then formulation C. Accordingly, differences in preparations were presumably caused by variations in manufacturing specifications, such as types of additives and their content and coating methods used. In other words, the characteristics of each product were revealed by evaluation of their physical properties, sensing of taste and smell, and human gustatory sensation tests.View full abstractDownload PDF (1796K) -
Venkatapuram Padmavathi, Bhumireddy Chinnachennaiahgari Venkatesh, Akk ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 449-458
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe reactivity of gem cyanoester ketene dithiolates towards the development of a variety of heterocycles was studied and tested for antioxidant property. The compounds bis benzoxazolylmethylthiomethylene pyrazoles and isoxazoles displayed excellent radical scavenging activity when compared with the standard ascorbic acid.View full abstractDownload PDF (937K) -
Atsushi Sakurai, Toshiro Sakai, Kazuhiro Sako, Yoshie MaitaniArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 459-464
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe purpose of this study was establishing a solid dispersion formulation containing a low glass transition temperature (Tg) and poorly water-soluble drug. Drug/polymer blends with differing physicochemical stabilities and oral absorption were prepared from copolyvidone (PVP-VA), polyvinylpyrrolidone (PVP) or hydroxypropylmethylcellulose (HPMC) by a hot melt extrusion. HPMC drastically increased the drug oral absorption property, while PVP-VA or PVP stabilized solid dispersions during storage by increasing the Tg in proportion to polymer concentration. Experimental Tg values corresponded closely with theoretical Tg values; indeed, the Tg values of solid dispersion with HPMC did not increase significantly compared to the Tg value for the drug alone. A solid dispersion formulation incorporating two different polymers—HPMC and either PVP-VA or PVP—maintained increased Tg, physicochemical stability, solubility, and bioavailability of the solid dispresions owing to each polymer. These findings suggested that both oral absorption and physicochemical stability of low-Tg drug will be improved using less amount of solid dispersion of combined two polymers than polymer alone.View full abstractDownload PDF (1228K) -
Namdev Borhade, Asif Rahimkhan Pathan, Somnath Halder, Manoj Karwa, Mi ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 465-481
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESS
Supplementary materialIn continuation of our efforts to discover novel nitric oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) as potentially “Safe NSAIDs,” we report herein the design, synthesis and evaluation of 21 new NO-NSAIDs of commonly used NSAIDs such as aspirin, diclofenac, naproxen, flurbiprofen, ketoprofen, sulindac, ibuprofen and indomethacin. These prodrugs have NO-releasing disulfide linker attached to a parent NSAID via linkages such as an ester (compounds 9–16), a double ester (compounds 17–24), an imide (compounds 25–30) or an amide (compounds 31–33). Among these NO-NSAIDs, the ester-containing NO-aspirin (9), NO-diclofenac (10), NO-naproxen (11), and the imide-containing NO-aspirin (25), NO-flurbiprofen (27) and NO-ketoprofen (28) have shown promising oral absorption, anti-inflammatory activity and NO-releasing property, and also protected rats from NSAID-induced gastric damage. NO-aspirin compound 25, on further co-evaluation with aspirin at equimolar doses, exhibited comparable dose-dependent pharmacokinetics, inhibition of gastric mucosal prostaglandin E2 (PGE2) synthesis and analgesic properties to those of aspirin, but retained its gastric-sparing properties even after doubling its oral dose. These promising NO-NSAIDs could therefore represent a new class of potentially “Safe NSAIDs” for the treatment of arthritic pain and inflammation.View full abstractDownload PDF (1358K) -
Laxmikant Ramvallabh Zawar, Sanjay Baburao BariArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 482-487
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe influence of microwave technology on the in vitro dissolution rate and in vivo antihyperglycemic activity of a poorly water soluble drug, repaglinide (RG) was studied. Solid dispersions were prepared by conventional fusion method and microwave method using poloxamer 188. The dispersions were characterized by solubility study, dissolution study, Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), X-ray powder diffraction (XRD) and scanning electron microscopy (SEM). Microwave generated solid dispersions exhibited remarkable improvement in solubility and dissolution rate compared to that of pure RG. Results of DSC, XRD and SEM study showed conversion of crystalline form of RG to amorphous form. In vivo studies revealed that the microwave generated solid dispersion showed significant improvements in antihyperglycemic activity as compared to RG alone, thus confirming the advantage of improved pharmacological activity of RG by microwave method. In conclusion, microwave method could be considered as simple, efficient and solvent free promising alternative method to prepare solid dispersion of poorly water soluble drug RG with significant enhancement in solubility, dissolution rate and antihyperglycemic activity.View full abstractDownload PDF (1708K) -
Maki Seki, Osamu Tsuruta, Yukio Aoyama, Aki Soejima, Hiroshi Shimada, ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 488-498
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSIn investigating potent sodium (Na+) channel blockers for the treatment of ischemic stroke, we synthesized a novel series of 3-amino-1-(5-indanyloxy)-2-propanol derivatives and evaluated their inhibitory effects on neuronal Na+ channels. The 3-amino-1-(5-indanyloxy)-2-propanol derivatives exhibited potent blocking activity for Na+ channels and a significantly low affinity for dopamine D2 receptors, which demonstrates a minimal clinical risk for extrapyramidal side effects. In particular, compound 4b, a 3-amino-1-(5-indanyloxy)-2-propanol derivative bearing a benzimidazole moiety, showed desirable neuroprotective activity in a rat transient middle cerebral artery occlusion model. Furthermore, compound 4b displayed a high binding affinity for neurotoxin receptor site 2 of the Na+ channels, which suggests that 4b would act as a use-dependent Na+ channel blocker in sustained depolarization during ischemic stroke.View full abstractDownload PDF (1189K) -
Hiroaki Aoshima, Toshio Miyase, Tsutomu WarashinaArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 499-507
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSEight new caffeic acid oligomers, clinopodic acids J–Q (1–8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC50 (19 µM) among the 22 compounds isolated from this plant.View full abstractDownload PDF (2096K) -
Tomoko Yamaguchi, Shinya Watanabe, Yuriko Matsumura, Yoshikazu Tokuoka ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 508-512
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSVanadium complexes with different ligands were synthesized and evaluated for antiproliferative activity on U937 cells. The alkyl chain length of the ligands affected the antiproliferative activity, and two complexes—3b and 4—exhibited strong activities with IC50 values of 6.02 and 3.90 μM respectively. Annexin V staining and DNA ladder formation indicated that these complexes induced apoptosis in U937 cells.View full abstractDownload PDF (2254K) -
Dun Wang, Like Hou, Lirong Wu, Xin YuArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 513-520
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe design, synthesis and biological evaluation of a novel series of oxazinyl isoflavonoids is described. Several analogs were shown to exhibit growth inhibitory effects against SKOV-3, DU-145 and HL-60 human colon cancer cell lines with IC50 values in the micromolar range. The cellular potency of compounds 7e and 12h were found to have greater in vitro inhibitory activities than phenoxodiol, the parental compound currently in late-stage clinical trials for the treatment of cancer. The results shown are suitable for further lead optimization.View full abstractDownload PDF (955K) -
Azza Taher Taher, Amira Atef HelwaArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 521-530
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSStarting from 6-aryl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4a–d), a series of mono- and dialkyl derivatives 5a–j and 6a, b was synthesized. Hydrazinolysis of 4a, b, d and 5d afforded the hydrazino derivatives 7a–c which were cyclised to give the triazolopyrimidinones 8a–c and the pyrimidotriazinones 9a–c through the reaction with formic acid and chloroacetyl chloride, respectively. Most of the newly synthesized compounds were evaluated for their in-vitro antitumor activity. Compounds 6a and b displayed promising anticancer activity against leukaemia, non-small cell lung, melanoma, and renal cancer. On the other hand, all compounds prepared were screened for their in-vitro antibacterial and antifungal activities. Compounds 5h and j showed significant activity against Staphylococcus aureus, while compounds 5e, 7c and 8c displayed moderate inhibitory activity against Candida albicans.View full abstractDownload PDF (741K) -
Ying Li, Shota Yoshida, Yvonne Chondo, Hossam Nassar, Ning Tang, Yuki ...Article type: Regular Article
2012 Volume 60 Issue 4 Pages 531-535
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSAn on‑line concentration and fluorescence determination HPLC for polycyclic aromatic hydrocarbons (PAHs) in seawater was proposed. An online concentration column packed with octadecyl polyvinyl alcohol polymer, a pump and a column switching valve were introduced in the conventional HPLC with a fluorescence detector. Only 1.0–100 mL seawater sample was introduced into the concentration column at 1.0 mL min−1 without any other pretreatment except filtration. Then the trapped PAHs totally flew into the separation column and eluted separately to be detected fluorogenically. The proposed method had good linearity with correlation coefficients (r) ranged from 0.951 to 0.998, and limits of detection ranged from 0.002 to 0.50 ng L−1 for 15 PAHs as 100 mL seawater was loaded. The sensitivity of the method was 10 to 100 times higher than those reported by other works. The proposed method was applied to the determination of PAHs in the seawater samples collected in the Japan Sea with satisfactory results and to check the present benzo[a]pyrene concentration at the beaches in Noto peninsula, Japan polluted with C-heavy oil spilled from the tanker in 1997.View full abstractDownload PDF (522K) -
Shingo Kikuchi, Yoshinori Onuki, Hideto Kuribayashi, Kozo TakayamaArticle type: Regular Article
2012 Volume 60 Issue 4 Pages 536-542
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSWe reported previously that sustained release matrix tablets showed zero-order drug release without being affected by pH change. To understand drug release mechanisms more fully, we monitored the swelling and erosion of hydrating tablets using magnetic resonance imaging (MRI). Three different types of tablets comprised of polyion complex-forming materials and a hydroxypropyl methylcellulose (HPMC) were used. Proton density- and diffusion-weighted images of the hydrating tablets were acquired at intervals. Furthermore, apparent self-diffusion coefficient maps were generated from diffusion-weighted imaging to evaluate the state of hydrating tablets. Our findings indicated that water penetration into polyion complex tablets was faster than that into HPMC matrix tablets. In polyion complex tablets, water molecules were dispersed homogeneously and their diffusivity was relatively high, whereas in HPMC matrix tablets, water molecule movement was tightly restricted within the gel. An optimal tablet formulation determined in a previous study had water molecule penetration and diffusivity properties that appeared intermediate to those of polyion complex and HPMC matrix tablets; water molecules were capable of penetrating throughout the tablets and relatively high diffusivity was similar to that in the polyion complex tablet, whereas like the HPMC matrix tablet, it was well swollen. This study succeeded in characterizing the tablet hydration process. MRI provides profound insight into the state of water molecules in hydrating tablets; thus, it is a useful tool for understanding drug release mechanisms at a molecular level.View full abstractDownload PDF (7386K)
Notes
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Min-Soo Kim, Ha-Seung Song, Hee Jun Park, Sung-Joo HwangArticle type: Note
2012 Volume 60 Issue 4 Pages 543-547
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe aims of this study were to identify how the solvent selection affects particle formation and to examine the effect of the initial drug solution concentration on mean particle size and particle size distribution in the supercritical antisolvent (SAS) process. Amorphous atorvastatin calcium was precipitated from seven different solvents using the SAS process. Particles with mean particle size ranging between 62.6 and 1493.7 nm were obtained by varying organic solvent type and solution concentration. By changing the solvent, we observed large variations in particle size and particle size distribution, accompanied by different particle morphologies. Particles obtained from acetone and tetrahydrofuran (THF) were compact and spherical fine particles, whereas those from N-methylpyrrolidone (NMP) and dimethylsulfoxide (DMSO) were agglomerated, with rough surfaces and relatively larger particle sizes. Interestingly, the mean particle size of atorvastatin calcium increased with an increase in the boiling point of the organic solvent used. Thus, for atorvastatin particle formation via the SAS process, particle size was determined mainly by evaporation of the organic solvent into the antisolvent phase. In addition, the mean particle size was increased with increasing drug solution concentration. In this study, from the aspects of particle size and solvent toxicity, acetone was the better organic solvent for controlling nanoparticle formation of atorvastatin calcium.View full abstractDownload PDF (4285K) -
Takaya Hoshikawa, Kei Tanji, Jun-ichi Matsuo, Hiroyuki IshibashiArticle type: Note
2012 Volume 60 Issue 4 Pages 548-553
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSIntramolecular [2+2] cycloaddition of γ,δ-unsaturated ketenes derived from hex-5-enoyl chloride derivatives gave bicyclo[2.1.1]hexan-5-ones with complete regioselectivity.View full abstractDownload PDF (476K) -
Hari Prasad Devkota, Masato Watanabe, Takashi Watanabe, Shoji YaharaArticle type: Note
2012 Volume 60 Issue 4 Pages 554-556
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSOne new C-methyl flavanone glucoside, farrerol 4′-O-β-D-glucopyranoside (1) was isolated from the aerial parts of Diplomorpha canescens (MEISN.) C. A. MEYER. Fourteen known phenolic compounds such as farrerol (2), luteolin 7-methyl ether 5-O-β-D-glucopyranoside (3), (−)-pinoresinol (4), (−)-lariciresinol (5), (−)-dihydrosesamin (6), (±)-dehydrodiconiferyl alcohol (7), rutarensin (8), umbelliferone (9), coniferyl aldehyde (10), sinapyl aldehyde (11), p-coumaric acid methyl ester (12), p-hydroxybenzaldehyde (13), p-hydroxyacetophenone (14) and syringaldehyde (15) were also isolated for the first time from this plant. Structure of 1 was determined on the basis of spectroscopic data including two dimensional (2D)-NMR, circular dichroism (CD) and by the application of Klyne’s rule.View full abstractDownload PDF (512K) -
Ping-Chung Kuo, Yi-Hsien Chen, Yann-Lii Leu, Chieh-Hung Huang, Yu-Ren ...Article type: Note
2012 Volume 60 Issue 4 Pages 557-561
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSA new and efficient synthetic pathway employed the aldol condensation between the acetophenone (3) and vanillin derivative (4) resulted in the precursor chalcone intermediate (14). The target compound viscolin (1) could be afforded through the hydrogenation of the chalcone and followed by deprotection. The present strategy described the development of a more efficient procedure that allowed large-scale production of viscolin for the further research of biological activity both in vitro and in vivo.View full abstractDownload PDF (505K) -
Naoko Fujiwara, Masako Kinoshita, Akira Uchida, Machiko Ono, Keisuke K ...Article type: Note
2012 Volume 60 Issue 4 Pages 562-570
Published: April 01, 2012
Released on J-STAGE: April 01, 2012
JOURNAL FREE ACCESSThe reactions of (±)-α-epoxy drimenol (4) and (±)-α-epoxy drimenyl cyanide (6) with acids (proton acid or Lewis acid) selectively gave the rearranged aldehyde (±)-13 and (±)-15 having the hydroindane skeleton, respectively, while the reactions of (±)-4 and (±)-6 with Dibal-H selectively afforded the allyl alcohol (±)-14 and (±)-16, respectively. The reactions of (8aR)-6 and (8aS)-6 with Dibal-H were applied for the determination of the absolute structure of natural 7β-acetoxy-ent-labda-8(17),13(14)E-dien-15-ol (18). The reaction of (±)-α-epoxy bicyclofarnesol (5) and (8aS)-5 with proton acid selectively provided the rearranged ketol (±)- and (8aS)-31 having the hydroindane skeleton, respectively. The optically active (8aS)-31 was converted to the natural (9S)-austrodoric acid (33).View full abstractDownload PDF (997K)
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