Download the Free Unbound MEDLINE PubMed App to your smartphone or tablet.
Available for iPhone, iPad, iPod touch, and Android.
Chem Pharm Bull [journal]
- Germacranolides and their Diversity of Eupatorium heterophyllum Collected in PR China. [JOURNAL ARTICLE]
- Chem Pharm Bull (Tokyo) 2014 Sep 10.
Eight new hydroperoxides and a new enone of germacrane-type sesquiterpenoids were isolated from the aerial parts of eight different samples of Eupatorium heterophyllum DC. (Asteraceae) collected in PR China. The structures were determined based on spectroscopic analyses. Seven of the eight samples produced hiyodorilactone A as a major constituent, while one afforded neither hiyodorilactone nor hydroperoxide. The results indicated the presence of diversity within this species.
- Synthesis of Antifungal Evaluation of 2H-[1,2,3]Triazolo[4,5-g]isoquinoline-4,9-diones. [JOURNAL ARTICLE]
- Chem Pharm Bull (Tokyo) 2014 Sep 5.
2H-[1,2,3]Triazolo[4,5-g]isoquinoline-4,9-diones and 2H-[1,2,3]triazolo[4,5-g]quinoline-4,9-diones were synthesized and tested for in vitro antifungal activity against pathogenic fungi. Many of those synthesized showed potent antifungal activity. Compounds 3a, 3b, 3g, and 3h completely inhibited the growth of all fungal species tested at the MIC level of 0.8~12.5 μg/mL. The results suggest that 2H-[1,2,3]triazolo[4,5-g]isoquinoline-4,9-diones could be antifungal agents.
- Synthesis and Antibacterial Activity of Cinnamaldehyde Acylhydrazone with a 1,4-Benzodioxan Fragment as a Novel Class of Potent β-Ketoacyl-Acyl Carrier Protein Synthase III (FabH) Inhibitor. [JOURNAL ARTICLE]
- Chem Pharm Bull (Tokyo) 2014 Sep 5.
Fatty acid biosynthesis is essential for bacterial survival. β-Ketoacyl-acyl carrier protein (ACP) synthase III (FabH), is a particularly attractive antibacterial target, since it is central to the initiation of fatty acid biosynthesis. Three series of 21 cinnamaldehyde acylhydrazone derivatives, A3-A9, B3-B9, and C3-C9, were synthesized and evaluated for FabH-inhibitory activity. Compound B6 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis (MIC values: 1.56-3.13 μg/mL) and was comparable with the positive control. Docking simulation by positioning compound B6 in the FabH structure active site was performed to explore the possible binding model.
- A Lanostane Triterpenoid and Three Cholestane Sterols from Tilia kiusiana. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):937-41.
Kiusianins A-D (1-4) were isolated from the leaves of a Japanese endemic plant, Tilia kiusiana, together with 14 known compounds. The structures of a new lanostane-type triterpenoid 1 and three new cholestane-type sterols 2-4 were elucidated by spectroscopic methods, including two dimensional (2D) NMR. All the compounds isolated were evaluated for their cytotoxicity against two human cancer cell lines, HeLa and HL-60.
- Inhibition of the thioesterase activity of human Fatty Acid synthase by 1,4- and 9,10-diones. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):933-6.
Fatty acid synthase (FASN) is the enzyme that synthesizes fatty acids de novo in human cells. Although FASN is generally expressed at low levels in most normal tissues, its expression is highly upregulated in many cancers. Consistent with this notion, inhibition of FASN activity has demonstrated potential to halt proliferation and induce cell death in vitro and to block tumor growth in vivo. Consequently, FASN is widely recognized as a valuable therapeutic target. In this report, we describe a variety of 1,4-quinones and 9,10-anthraquinones, including several natural compounds and some newly synthesized compounds, that potently inhibit the thioesterase (TE) domain of FASN. Inhibition of recombinant TE activity, inhibition of cellular FASN, and cytotoxicity in human prostate cancer cell lines and normal fibroblasts, is shown for the most potent inhibitors. Collectively, the data illustrate the novel inhibitory capacity of the 1,4-quinone and 9,10-anthraquinone pharmacophores against FASN.
- α-Heteroarylation of Ketones via the Umpolung Reaction of N-Alkoxyenamine. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):927-32.
A new method has been developed for the umpolung α-heteroarylation of ketones via an N-alkoxyenamine. The treatment of ketones with tris(heteroaryl)aluminum reagents in the presence of isoxazolidine gave the corresponding α-heteroarylated ketones in moderate to good yields.
- Synthesis and anticancer evaluation of benzyloxyurea derivatives. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):898-905.
A series of novel benzyloxyurea derivatives was designed, synthesized by substituting different benzyls or phenyls on N,N'-positions of the hydroxyurea (HU). These target compounds were evaluated for their anticancer activity in vitro against human leukemia cell line K562 and murine leukemia cell line L1210 in comparison with HU by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Some of the compounds showed promising anticancer activity against the cells. Molecular docking experiments with Saccharomyces cerevisiae R1 domain indicated that 4a and 4f' have stronger affinity than 4m and 4n. Flow cytometry study showed that compound 4g exerted greater apoptotic activity against K562 cells line than HU.
- Adsorption of Tungsten onto Zeolite Fly Ash Produced by Hydrothermally Treating Fly Ash in Alkaline Solution. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):892-7.
Fly ash (FA) was hydrothermally treated in an alkaline solution to produce zeolite fly ash (Z-FA). The properties of the FA and Z-FA were investigated. The amounts of tungsten (W) adsorbed onto the FA and Z-FA surfaces were evaluated. Z-FA was produced by hydrothermally treating FA in an alkaline solution. The specific surface area and pore volume of the Z-FA were greater than those of the FA. More W was adsorbed onto the Z-FA surface than onto the FA surface. The adsorption isotherms for W were fitted using both the Freundlich and Langmuir equations. The equilibrium concentrations of W adsorbed onto the FA and Z-FA surfaces were subsequently reached within 20 h. The pseudo-second-order model more accurately described the data than did the pseudo-first-order model. Sodium hydroxide solutions (1-50 mmol/L) were used to easily recover W from Z-FA, indicating that Z-FA was useful for recovering W from aqueous solutions.
- Synthesis and Biological Evaluation of 3-Methyl-5-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione Derivatives for the Treatment of Diet-Induced Obesity. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):883-91.
Triglycerides are the main part of fats and half of the lipids in hepatocytes, and play an important role in metabolism as energy sources and transporters of dietary fat. In this study, 33 derivatives based on 3-methyl-5-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione were synthesized and evaluated for their lipid-lowering activity. Among them, compound 1i was found to exhibit potent triglyceride-lowering potency in 3T3-L1 adipocytes which was comparable to that of the adenosine monophosphate-activated protein kinase (AMPK) agonist Acadesine (AIACR). Furthermore, oral administration of 1i at a dose of 50 mg kg(-1) d(-1) for 5 weeks could reduce the mean body weight and liver weight by 12.02% and 32.00%, respectively, and regulated serum levels of triglycerides in diet-induced obese mice. The results indicate that compound 1i is a potential small-molecule for the treatment of diet-induced obesity and related diseases.
- Fabrication, Characterization and Pharmacokinetic Evaluation of Doxorubicin-Loaded Water-in-Oil-in-Water Microemulsions Using a Membrane Emulsification Technique. [Journal Article]
- Chem Pharm Bull (Tokyo) 2014; 62(9):875-82.
Doxorubicin (DOX)-loaded water-in-oil-in-water (W/O/W) microemulsions were produced using a shirasu-porous-glass (SPG) membrane emulsification technique. Soybean oil was used as the oil phase; polyglycerol polyricinoleate (PGPR) or tetraglycerol polyricinoleate (TGPR) was used as the surfactant to stabilize the feed W/O emulsions, while Tween 20 was used in the external water phase to stabilize oil droplets containing water droplets. Increasing the feed pressure from 50 to 90 kPa increased the particle size of W/O/W emulsions, whereas it was decreased by increasing the agitator speed. The smallest particle sizes of multiple emulsions were obtained at the feed pressure of 50 kPa and agitator speed of 350 rpm. Under this set of conditions, the increase in the concentration of PGPR or TGPR showed a decrease in the particle size of DOX-loaded W/O/W emulsions. The optimized formulation comprising of 5% w/v PGPR and 3% w/v Tween 20 in the oil phase and external water phase, respectively, with 0.5% w/v of DOX had a particle size of 0.440±0.007 µm and polydispersity index of 0.220±0.087, which was supported by the transmission electron microscopy image. The formulations showed a sustained release profile in phosphate buffer solution (pH 7.4). The plasma concentrations of DOX after intravenous administration to rats were prolonged and gave approximately 17-fold higher area under the drug concentration-time curve (AUC) compared to free DOX solution. Thus, these results demonstrated that the SPG membrane emulsification technique could be used as a promising technique to prepare W/O/W microemulsions for delivering DOX with sustained release characteristics and better bioavailability.