Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 57, Issue 9
Displaying 1-24 of 24 articles from this issue
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Review
  • Explorative Study on Isoform-Selective Histone Deacetylase Inhibitors
    Takayoshi Suzuki
    Article type: Review
    2009 Volume 57 Issue 9 Pages 897-906
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.897
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    Histone deacetylases (HDACs) catalyze the deacetylation of the acetylated lysine residues of histones and non-histone proteins, and are involved in various fundamental life phenomena, such as gene expression and cell cycle progression. Thus far, eighteen HDAC family members (HDAC1—11 and SIRT1—7) have been identified, but the functions of the HDAC isoforms are not yet fully understood. In addition, some of the HDAC isoforms have been suggested to be associated with various disease states, including cancer and neurodegenerative disorders. Therefore, isoform-selective HDAC inhibitors are of great interest, not only as tools for probing the biological functions of the isoforms, but also as candidate therapeutic agents with few side effects. It was against this background that we initiated research programs to identify isoform-selective HDAC inhibitors. We designed HDAC inhibitors based on the three-dimensional structure of the enzyme and on the proposed catalytic mechanism of HDACs, and found several isoform-selective HDAC inhibitors. Furthermore, we elucidated the functions of HDAC6 by chemical genetic approaches using these inhibitors. The results of this research also suggested the feasibility of using isoform-selective HDAC inhibitors as therapeutic agents.
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Regular Articles
  • Design of Nateglinide Controlled Release Tablet Containing Erosion Matrix Tablet and Multiple Administration Study in Normal Beagle Dogs
    Chisato Makino, Hidetoshi Sakai, Akira Okano, Akira Yabuki
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 907-913
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.907
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    We designed a single unit type tablet formulation containing nateglinide to decrease both postprandial blood glucose level (PBG) and fasting blood glucose level (FBG) in normal beagle dogs. The tablet was a dry coated tablet comprising both a core tablet (an erosion matrix tablet: a controlled release portion(nateglinide: 90 mg)) and an outer shell (an immediate release portion (nateglinide: 60 mg)). The weight, the diameter and the hardness of the obtained tablet were 416.1 mg, 10 mmφ, about 60 N, respectively. The dissolution study of the obtained tablet in pH 1.2 or 6.8 showed that the nateglinide in the immediate release portion dissolved in almost 30 min., and that 30 min after the dissolution test started, the nateglinide in the controlled release portion had dissolved slowly. An in vivo single oral administration study using normal beagle dogs showed the bioavailability value of the obtained nateglinide dry coated tablets against nateglinide immediate release tablets was 73.6%, although the value of nateglinide controlled release tablets containing enteric coated granules was 57.2—60.8%. An in vivo multiple oral administration study (b.i.d. (interval: 12 h), 8 d) using normal beagle dogs showed the reproducibility of nateglinide absorption. In addition, decreases in both PBG and FBG were observed. The ability to decrease the blood glucose level did not weaken during a multiple administration. On the basis of the above results, a controlled release formulation containing a short-acting type oral blood glucose regulator, not only nateglinide but meglitinides (repaglinide, mitiglinide, etc.) was suggested to enable control of both PBG and FBG for moderate and severe diabetes patients.
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  • Design and Evaluation of Polymeric Ocular Drug Delivery System
    Ashish Prakash Gorle, Suredra Ganeshlal Gattani
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 914-919
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.914
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    The objective of the present study was to prepare ocular inserts of Gatifloxacin. The inserts were fabricated by solvent casting technique, with an aim by achieving once a day administration in the treatment of conjunctivitis. Inserts were evaluated for film thickness, weight variation, drug content, percentage moisture absorption and loss. In-vitro drug release studies were done using bi-chambered donar receiver compartment model. The optimized formulations were subjected to in-vivo studies using rabbits as an animal model and stability studies to assess the effectiveness of the formulations. Finally in-vitro and in-vivo correlation was established. In-vitro drug release data was treated according to zero, first, Korsemeyer Peppas and Higuchi kinetics to access the mechanism of drug release. Formulations were found to be uniform in physicochemical parameter with a fewer variations. Plasticizer was found to influence in mechanical properties as well as modify the drug release rate of the films. Prepared ocular inserts exhibited desired release within 24 h and found to be strongly revealing the efficacy of in vitro–in vivo correlation. From stability studies inserts were remained stable both physically and chemically. No burst effect but a prolonged drug release was observed from all formulations. Thus it achieves target such as increased residence time, prolonged drug release, reduction in frequency of administration and may improve the patient compliance.
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  • Synthesis and Biological Activity of Enantiomeric Pairs of 5-(Alk-2-enyl)thiolactomycin and 5-[(E)-Cycloalk-2-enylidenemethyl]thiolactomycin Congeners
    Kohei Ohata, Shiro Terashima
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 920-936
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.920
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    The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure–activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2-enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.
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  • Study on Mechanism for Amorphous Drug Stabilization Using Gelucire 50/13
    Shamkant Laxman Shimpi, Kakasaheb Ramoo Mahadik, Anant Raghunath Parad ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 937-942
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.937
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    Methods of preparation and application of amorphous form are well established but it is equally important to note that devitrification of amorphous drugs has limited their applications. Present study was performed to investigate mechanism for amorphous drug stabilization using Gelucire in comparison with polyvinylpyrrolidone (PVP). Etoricoxib and celecoxib were taken as model drugs for this study, as etoricoxib has only proton accepting site for hydrogen bonding in comparison with celecoxib, which has both proton accepting and donating site. Solid dispersion of celecoxib with polyvinylpyrrolidone and Gelucire was prepared by spray drying and melt-granulation technique respectively. X-ray powder diffractometry and differential scanning calorimetry were used to study the physical state of the drug. Dissolution studies were performed to differentiate dissolution performance. Stability study samples were evaluated for physical state of the drug and dissolution performance. An IR study in correlation with molecular modeling was carried out to study the mechanism for stabilization. Dissolution of melt-granulation of amorphous celecoxib was improved significantly as compared to amorphous celecoxib and Celecoxib-PVP solid dispersion. Melt-granulation with lipid seemed to be more dominant than amorphization of drug for improving dissolution. Stability data revealed that PVP was significantly advantageous for amorphous form stabilization whereas Gelucire failed in case of Celecoxib. In contrast to this, our previous study revealed the stabilization ability of Gelucire for amorphous etoricoxib. Molecular modeling and IR studies revealed that H-bonding was predominant mechanism for stabilization. Out of two proposed mechanism for amorphous drug stabilization by lipids, H-bonding ability is more dominant than immobilization of molecule in lipid matrix.
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  • Calculating the Critical Relative Humidity from the Solubility of Electrolyte According to Extended Non-random Two Liquid Model
    Yingli Wang, Xiancheng Zhan, Chaoqun Xiang, Jia Chen, Lan Cao, Manzhou ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 943-947
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.943
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    According to thermodynamic principle, the critical relative humidity of electrolytes is closely related to their solubility. The authors explored the relationship theoretically and calculated the critical relative humidity of 21 electrolytes in the light of Raoult's law, modified Debye–Hückel model and extended non-random two liquid (NRTL) model from their solubility. The results indicate that the critical relative humidity values calculated by Raoult's law can not accord with the reported ones and there is a systematic error in high concentration range; the values calculated by modified Debye–Hückel model still can not accord with the reported ones well although without systematic error; and the values calculated by extended NRTL are comparable to the reported ones.
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  • Analyses of Biologically Active Steroids: Antitumor Active OSW-1 and Cardiotonic Marinobufotoxin, by Matrix-Assisted Laser Desorption/Ionization Quadrupole Ion Trap Time-of-Flight Tandem Mass Spectrometry
    Hiroko Kasai, Masayoshi Tsubuki, Kazutake Shimada, Toshio Nambara, Tos ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 948-956
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.948
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    Naturally occurring constituents of biological or pharmaceutical interest often exist in the form of glycosides or conjugates. Mass spectral investigations of these compounds require soft ionization techniques if information on molecular mass, sugar sequence, or conjugate content is desired. In this study, matrix-assisted laser desorption/ionization (MALDI) quadrupole ion trap (QIT) time-of-flight tandem mass spectrometry (TOF-MSn) was used to identify both OSW-1, an acetylated cholestane diglycoside showing antitumor activity, and the cardiotonic steroid, bufotoxin. Each molecular-related ion was identified, and subsequent collision-induced dissociation experiments in which a molecular-related ion was selected as a precursor ion produced the characteristic product ions that are essential for structural elucidation. OSW-1 and its analogue with a modified side chain, thienyl OSW-1, were synthesized, and bufotoxins, i.e., marinobufotoxin and its homologue, marinobufagin 3-pimeloylarginine ester, were isolated from toad venom. On MALDI-TOF-MS, sodium-adduct [M+Na]+ ions were observed in the steroid glycosides, although protonated [M+H]+ ions were relatively more abundant than sodium-adduct [M+Na]+ ions in the bufotoxins. On the basis of tandem MS results, we propose key fragmentation pathways. The sugar moiety or side chain from the precursor ion was eliminated in OSW-1. However, characteristic product ions originating from the cleavage of the side chain with an ester formation were observed in the bufotoxins. Post-source decay (PSD) on MALDI-TOF-MS is also described when evaluating α-cyano-4-hydroxycinnamic acid or 2,5-dihydroxybenzoic acid as a matrix to obtain useful ions required for the identification of compound.
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  • Absolute Stereostructures of Olibanumols A, B, C, H, I, and J from Olibanum, Gum-Resin of Boswellia carterii, and Inhibitors of Nitric Oxide Production in Lipopolysaccharide-Activated Mouse Peritoneal Macrophages
    Masayuki Yoshikawa, Toshio Morikawa, Hideo Oominami, Hisashi Matsuda
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 957-964
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.957
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    Three new monoterpenes, olibanumols A (1), B (2), and C (3), and three new triterpenes, olibanumols H (4), I (5), and J (6), were isolated from olibanum, the exuded gum-resin from Boswellia carterii BIRDW. Their structures including the absolute configuration were determined by chemical and physicochemical evidence. Among the constituents, olibanumols A (1), H (4), and I (5), and isofouquierol (12) exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.
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  • Preparation of Four Types of Coenzyme Q10/γ-Cyclodextrin Supramolecular Complexes and Comparison of Their Pharmaceutical Properties
    Taishi Higashi, Katsunori Nishimura, Ayumi Yoshimatsu, Haruna Ikeda, K ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 965-970
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.965
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    In this study, we prepared four kinds of complexes of Coenzyme Q10 (CoQ10) with γ-cyclodextrin (γ-CyD) by the kneading methods and the solubility methods with or without heating, and compared their pharmaceutical properties. Differential scanning calorimetrical curves and powder X-ray diffraction patterns showed that the complexes formed pseudorotaxane-like supramolecular structure, although included free γ-CyD and CoQ10, when prepared by the kneading method and solubility method without heating. At the preparation process, a heating improved the complexation of CoQ10 with γ-CyD in the both methods. The dispersion rate of CoQ10 in water increased in the order of CoQ10 alone≈physical mixture with γ-CyD≪solubility/heating product<solubility product<kneading/heating product<kneading product, possibly due to submicron-ordered particle formulation. Of the various ointments containing CoQ10 alone, the release of CoQ10 from hydrophilic ointment was fastest. In addition, the release rate of CoQ10 from hydrophilic ointment in the solubility/heating product was markedly increased, compared to that in the CoQ10/γ-CyD physical mixture and the other complexes. The fast release of CoQ10 from hydrophilic ointment could be involved in propylene glycol in the ointment. These results suggest that supramolecular complexes of CoQ10 with γ-CyD can be prepared by various methods, and among various complexes the pseudorotaxane-like CoQ10/γ-CyD complexes prepared by the solubility method with heating have the potential for preparation of ointments.
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  • Androgen Modulators from the Roots of Paeonia lactiflora (Paeoniae Radix) Grown and Processed in Nara Prefecture, Japan
    Kazuto Washida, Yoshiyuki Itoh, Takashi Iwashita, Kyosuke Nomoto
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 971-974
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.971
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    The monoterpene glycoside, 3′-O-galloylpaeoniflorin (1), and four known compounds, 6′-O-galloylalbiflorin (2), pentagalloylglucose (3), 6′-O-benzoylpaeoniflorin (4) and 6′-O-galloylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan, as androgen modulators. Their structures were elucidated based on spectroscopic analysis. Compounds 2 and 3 showed strong androgen receptor (AR) binding activity (IC50 values 33.7 and 4.1 μg/ml, respectively), 1, 4 and 5 showed weak activity (20, 31 and 12% at 120 μg/ml, respectively). However, paeoniflorin (6) and albiflorin (7), the structures of which are related to 1, 2, 4 and 5, showed no activity. These results suggested that both the structure of albiflorin and the galloyl moiety are important for 2 to show strong AR binding activity. Furthermore, compounds 1—5 inhibited growth of an androgen-dependent LNCaP-FGC (prostate cancer cell line), and were indicated to be AR antagonists. Compounds 2 and 3 might be candidates as safe, natural anti-androgens.
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  • Two New Cleistanthane Diterpenes and a New Isocoumarine from Cultures of the Basidiomycete Albatrellus confluens
    Zhong-Yu Zhou, Rong Liu, Meng-Yuan Jiang, Ling Zhang, Yun Niu, Ying-Ch ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 975-978
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.975
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    Two new cleistanthane-type diterpenes, 3α,5α,8β-trihydroxycleistanth-13(17),15-dien-18-oic acid (1) and 8β-hydroxy-18-norcleistanth-4(5),13(17),15-trien-3-one (2), a new isocoumarine, 3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine (3), along with three known aurovertins, aurovertins B (4), C (5) and E (6), four known polyesters, orbuticin (7), BK223A (8), BK223B (9) and 15G256α-2-me (10), and a known isocoumarine, 3R-6-hydroxymellein (11), were isolated from cultures of the basidiomycete Albatrellus confluens. The structures of these compounds were established on the basis of spectroscopic and chemical methods.
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  • Synthesis and Evaluation of Pyrrolin-2-one Compounds, a Series of Plasminogen Activator Inhibitor-1 Inhibitors
    Hiroshi Miyazaki, Tsuyoshi Ogiku, Hiroshi Sai, Yasunori Moritani, Akio ...
    Article type: Regular Article
    2009 Volume 57 Issue 9 Pages 979-985
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.979
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    A novel series of furan-2-one and pyrrolin-2-one derivatives having PAI-1 (plasminogen activator inhibitor-1) inhibitory activity were synthesized and evaluated for their antithrombotic activity in a rat arterial thrombosis model. Among the synthesized compounds, 5f (T-1776Na) was found to have good selectivity for PAI-1 over other enzymes and high antithrombotic activity.
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Notes
  • Lupane Triterpene Glycosides from Leave of Acanthopanax koreanum and Their Cytotoxic Activity
    Nguyen Xuan Nhiem, Nguyen Huu Tung, Phan Van Kiem, Chau Van Minh, Yan ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 986-989
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.986
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    One new lupane-triterpene glycoside, acankoreoside I (1), and four known compounds, acankoreoside A (2), acankoreoside D (3), acankoreoside F (4), and acantrifoside A (5), were isolated from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D- and 2D-NMR spectroscopy. The structure of new compound 1 was determined to be 3α,11α,30-trihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester. The cytotoxic activities of these compounds were evaluated with four cancer cell lines such as A-549 (lung), HL-60 (acute promyelocytic leukemia), MCF-7 (breast), and U-937 (leukemia). Compound 1 showed growth inhibitory effect in A-549, HL-60, and MCF-7 cell lines with the IC50 values of 8.2 μM, 12.1 μM, and 28.6 μM, respectively, whereas it was less active in the U937 cell line (the IC50 >100 μM).
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  • Chemical Examination of the Sponge Phycopsis sp.
    Chinni Mahesh Kondempudi, Rajaram Singanaboina, Narasimhulu Manchala, ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 990-992
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.990
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    Two new compounds 7α,8α-epoxy theonellin isothiocyanate (1) and 5α,8α-epidioxyergosta-6Z,22Z,25-trien-3β-ol (2) along with two known compounds, theonellin isothiocyanate (3) and theonellin formamide (4) have been isolated from the sponge Phycopsis sp. Compound 2 showed cytotoxic activity against HL-60 and U937 human cancer cell lines with IC50 values of 5.96±0.02 and 31.72±0.55 μg/ml, respectively.
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  • Flavanoids and Pterocarpans from the Bark of Erythrina fusca
    Phongsak Innok, Thitima Rukachaisirikul, Apichart Suksamrarn
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 993-996
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.993
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    Three new isomeric flavanones, fuscaflavanones A1 (1), A2 (2) and B (3), together with six known flavanones, lupinifolin (4), lonchocarpol A (5), a mixture of lonchocarpols C1 and C2 (6a, b), and a mixture of lonchocarpols D1 and D2 (7a, b), five pterocarpans, sandwicensin (8), phaseollidin (9), erythrabissin I (10), and a mixture of dolichins A and B (11a, b), one chalcone, isobavachalcone (12), and one isoflavone, wighteone (13), were isolated from the bark of Erythrina fusca LOUR. Their structures were elucidated on the basis of spectroscopic data. Some isolates were tested for antiplasmodial and cytotoxic activities and it was found that 5 and 9 exhibited moderate antiplasmodial activity against Plasmodium falciparum. For cytotoxicity, compounds 1, 4, 5, 9 and 12 showed moderate to weak activity against KB, BC and NCI-H187 cells, whereas 2 exhibited only weak activity against KB cells.
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  • Four New Bibenzyl Derivatives from Dendrobium candidum
    Yan Li, Chun-Lan Wang, Ya-Jun Wang, Fang-Fei Wang, Shun-Xing Guo, Jun- ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 997-999
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.997
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    Four new bibenzyl derivatives, namely, dendrocandins F—I (1—4), were isolated from the stems of Dendrobium candidum. Their structures were elucidated by the analysis of spectroscopic data. Dendrocandins F and G represent the fourth and fifth example of bisbibenzyl derivates with a dibenzopyran ring between two units, respectively. Dendrocandin H represents the first example of a bibenzyl derivative formed by a bibenzyl and a 1,4-phenanthraquinone unit via a dibenzopyran ring. Compounds 1—4 were examined for antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay.
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  • Triterpenoid Saponins from the Stem Bark of Acanthopanax brachypus HARMS
    Hao-Bin Hu, Xu-Dong Zheng, Hong Cao, Xiao-Qiang Guo, Huai-Sheng Hu
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1000-1003
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1000
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    Two new triterpenoid saponins, brachyposide A (1) {3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester} and brachyposide B (2) {3-O-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→3)-β-D-glucuronopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester}, together with four known triterpenoid saponins, including tabguticoside A, nipponoside D, palmatoside E and ciwujianoside A1, were isolated from the stem bark of Acanthopanax brachypus. Their structures were elucidated on the basis of spectroscopic and chemical evidence.
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  • Design, Synthesis and Discovery of 1-(2-(6-Chloro-3-methylsulfonyl)-naphthyl)-1H-pyrazole-5-carboxylamides as Highly Potent Factor Xa Inhibitors
    Zhaozhong Jon Jia, Robert Murry Scarborough, Penglie Zhang, Sherin Hal ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1004-1007
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1004
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    Based upon the biphenyl 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides reported in our previous communications, we designed and discovered 2-(6-chloro-3-methylsulfonyl)-naphthyl as an optimal factor Xa S1 binding element. Employing a key Diels–Alder reaction of 1,4-dihydro-2,3-benzoxathiin-3-oxide with maleic anhydride and a key Cu(I)-mediated methylsulfonylation, we prepared two biphenyl 1-(2-(6-chloro-3-methylsulfonyl)-naphthyl)-1H-pyrazole-5-carboxylamides as highly potent factor Xa inhibitors with Ki values of 0.065 nM and 0.045 nM respectively, and demonstrated the synergistically enhanced binding interaction in the factor Xa S1 site.
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  • Two New Taxoids from the Leaves and Stems of Taxus chinensis
    Fu-Sheng Wang, Gui-Rong Shi
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1008-1010
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1008
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    Two new taxoids called 7,13-dideacetyl-9,10-debenzoyl-7β,9α-p-hydroxylbenzylidenedioxy-taxchinin C (1) and 7,13-dideacetyl-2,9,10-debenzoyl-2-tigloyl-7β,9α-p-hydroxylbenzylidenedioxy-taxchinin C (2) were isolated from the leaves and stems of Taxus chinensis. They represent the first examples of taxoids containing the 5/7/6-membered ring system with 7β,9α-p-hydroxylbenzylidenedioxy groups, the structures of which were elucidated based on spectroscopic analyses, especially 1D and 2D NMR spectra.
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  • Saponins from the Processed Rhizomes of Polygonatum kingianum
    He-Shui Yu, Bai-Ping Ma, Li-Ping Kang, Tao Zhang, Feng-Juan Jiang, Jie ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1011-1014
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1011
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    Two new spirostanol saponins, named kingianoside H (1) and kingianoside I (2), were isolated from the processed rhizomes of Polygonatum kingianum, along with a known triterpenoid saponin ginsenoside-Rc (3), four known spirostanol saponins Tg (4), (5), polygonatoside C1 (6) and ophiopogonin C′ (7). The structures of the new compounds were elucidated by detailed spectroscopic analyses, including 1D and 2D NMR techniques and chemical methods. Compounds 3 and 5 were first reported from the genus Polygonatum. Compounds 4, 6 and 7 are reported for the first time from the processed Polygonatum kingianum.
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  • Pungent Aromatic Compound from New Zealand Liverwort Hymenophyton flabellatum
    Masao Toyota, Ikuko Omatsu, John Braggins, Yoshinori Asakawa
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1015-1018
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1015
    JOURNAL FREE ACCESS
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    Ether extract of the New Zealand liverwort Hymenophyton flabellatum produced a pungent principle. The structure has been identified as known compound, 1-(2,4,6-trimethoxy-phenyl)-but-2(E)-en-1-one by means of its spectral data, previously isolated from the fern Arachinoides standishii. Further isolation of the extract of this species afforded eight aromatic compounds whose structures were determined by spectral analysis. Those compounds were shown to be biogenetically and structurally related to the pungent compound of this species.
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  • Interaction of Polyphenolic Metabolites with Human Serum Albumin: A Circular Dichroism Study
    Akiko Nozaki, Toshikiro Kimura, Hideyuki Ito, Tsutomu Hatano
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1019-1023
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1019
    JOURNAL FREE ACCESS
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    Binding sites of polyphenolic compounds on human serum albumin (HSA) were investigated using induced Cotton effects on the circular dichroism (CD) spectra. Polyphenolic compounds used in this study are known to be metabolites from tannins and their related polyphenols in food and medicinal plants. The present investigation revealed that the structural differences markedly affected the binding of the compounds to HSA. Protocatechuic acid, together with its methylated compounds vanillic and isovanillic acids, were assigned to be bound to sites I and II of HSA, based on the competitive relationships with site-I-binding phenylbutazone (PB) and site-II-binding diazepam (DP). 4-O-Methylgallic acid, which is the metabolite from gallic acid, was bound to site I on HSA, while gallic acid did not affect the binding of PB and DP at the concentration examined. Neither ellagic acid nor its metabolite urolithin A was competitive with PB and DP on HSA. The addition of digitoxin did not affect the induced CD of the polyphenolic acids examined.
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  • Chiral Amidophosphane–Rhodium(I)-Catalyzed Asymmetric Conjugate Arylation of Acyclic Enones with Arylboronic Acids
    Qian Chen, Masami Kuriyama, Xinyu Hao, Takahiro Soeta, Yasutomo Yamamo ...
    Article type: Notes
    2009 Volume 57 Issue 9 Pages 1024-1027
    Published: September 01, 2009
    Released on J-STAGE: September 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1024
    JOURNAL FREE ACCESS
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    A catalytic asymmetric conjugate arylation of acyclic α,β-unsaturated ketones with arylboronic acids was catalyzed by 3 mol% of chiral amidomonophosphane 1–rhodium(I) in the presence of potassium hydroxide in a mixture of 1,4-dioxane and water at 70 °C to afford 1,4-conjugate arylated acyclic ketones with high enantiomeric excess in high chemical yield. Thirteen examples of the reaction demonstrate the general applicability of the catalytic system.
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