Electrochemical oxidation of anti-tumor agent, etoposide.

Abstract:

:As part of a search for new potent derivatives, electrochemical oxidation of etoposide (1) was carried out under controlled potential (500 mV) to yield 1,2-dehydroetoposide (4), 4'-O-demethyl-1,2,3,4-tetradehydro-4-dehydroxy-podophyllotox in (5) and 1,2,3,4-tetradehydroetoposide (6). They showed no cytotoxicity against B16-melanoma.

authors

Obata R,Ohnuma T

doi

10.1248/cpb.41.1846

subject

Has Abstract

pub_date

1993-10-01 00:00:00

pages

1846-7

issue

10

eissn

0009-2363

issn

1347-5223

journal_volume

41

pub_type

杂志文章
  • Synthesis and biological activity of the metabolites of N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline fumarate (SK-946).

    abstract::Three metabolites of N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline fumarate (SK-946), a novel central muscarinic cholinergic receptor agonist, were prepared to confirm their proposed structures, and tested for muscarinic receptor affinity in vitro. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.880

    authors: Suzuki T,Inagaki H,Hamajima H,Uesaka H,Hori K,Ikami T

    更新日期:1999-06-01 00:00:00

  • Temperature-Dependent Formation of N-Nitrosodimethylamine during the Storage of Ranitidine Reagent Powders and Tablets.

    abstract::The purpose of this study was to elucidate the effect of high-temperature storage on the stability of ranitidine, specifically with respect to the potential formation of N-nitrosodimethylamine (NDMA), which is classified as a probable human carcinogen. Commercially available ranitidine reagent powders and formulations...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00431

    authors: Abe Y,Yamamoto E,Yoshida H,Usui A,Tomita N,Kanno H,Masada S,Yokoo H,Tsuji G,Uchiyama N,Hakamatsuka T,Demizu Y,Izutsu KI,Goda Y,Okuda H

    更新日期:2020-10-01 00:00:00

  • Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.

    abstract::Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric, monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of Cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic dat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2083

    authors: Hatano T,Ogawa N,Kira R,Yasuhara T,Okuda T

    更新日期:1989-08-01 00:00:00

  • Biologically active glycosides from Asteroidea, 41. Isolation and structure determination of glucocerebrosides from the starfish Linckia laevigata.

    abstract::A new glucocerebroside, linckiacerebroside A (1) and a known glucocerebroside S-2a-3 (2), have been isolated from the cerebroside molecular species obtained from the less polar fraction of the CHCl3/MeOH extract of the starfish Linckia laevigata, together with three pseudo homogeneous glucocerebroside, 3, 4, and 5. Th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1255

    authors: Maruta T,Saito T,Inagaki M,Shibata O,Higuchi R

    更新日期:2005-10-01 00:00:00

  • Study of 1,3,5-triazine-based catalytic amide-forming reactions: effect of solvents and basicity of reactants.

    abstract::Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid-base equilibrium among re...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00368

    authors: Kunishima M,Kitamura M,Tanaka H,Nakakura I,Moriya T,Hioki K

    更新日期:2013-01-01 00:00:00

  • Evaluation of new pregnane derivatives as 5alpha-reductase inhibitor.

    abstract::The objective of this study was to synthesize several new pregnane derivatives and evaluate them as antiandrogens. From the commercially available 16-dehydropregnenolone acetate (7), two new steroidal compounds were synthesized: 17alpha-hydroxy-17beta-methyl-16beta-phenyl-D-homoandrosta-1,4,6-triene-3,20-dione (18) an...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.525

    authors: Cabeza M,Heuze I,Bratoeff E,Ramírez E,Martínez R

    更新日期:2001-05-01 00:00:00

  • Synthesis and biological activities of metabolites of mosapride, a new gastroprokinetic agent.

    abstract::In order to confirm the proposed structures of two metabolites 3 and 4 of the gastroprokinetic agent mosapride [4-amino-5-chloro-2-ethoxy-N-([4-(4-fluorobenzyl)-2-morpholinyl] methyl)benzamide, 2], the compounds were synthesized and their biological activity was examined. The structures of the metabolites were confirm...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.699

    authors: Kato S,Morie T,Yoshida N

    更新日期:1995-04-01 00:00:00

  • Continuous monitoring of unbound flomoxef levels in rat blood using microdialysis and its new pharmacokinetic analysis.

    abstract::Microdialysis sampling method coupled to high-performance liquid chromatography with UV detection was applied to continuous monitoring of in vivo unbound flomoxef concentration in rat blood. By comparison with ultrafiltration method, it was demonstrated that it gave reliable results for the unbound drug monitoring in ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.808

    authors: Saisho Y,Umeda T

    更新日期:1991-03-01 00:00:00

  • The influence of aggregation of porphyrins on the efficiency of photogeneration of hydrogen peroxide in aqueous solution.

    abstract::The pH-dependence of the ability of coproporphyrin (CP) and uroporphyrin (UP) to photogenerate hydrogen peroxide (H2O2) in aqueous solution was investigated, with special attention to the structure-activity relationship related to the aggregation of the porphyrins. It was found that the efficiency was strongly depende...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1004

    authors: Komagoe K,Tamagake K,Katsu T

    更新日期:2006-07-01 00:00:00

  • Phospholipid dependency of hepatic uridine diphosphate-glucuronyltransferase in the developing fetus of the rat.

    abstract::The developmental change of uridine diphosphate-glucuronyltransferase (UDPGT) was studied using hepatic microsomes of rat fetuses on days 18 and 21 of gestation. Total phospholipid content was higher on day 21 than on day 18, although no significant difference in the composition between the two stages was observed. Li...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2454

    authors: Nanbo T

    更新日期:1991-09-01 00:00:00

  • Sesquiterpenes from the fruiting bodies of Ramaria formosa and their human neutrophil elastase inhibitory activity.

    abstract::Two new sesquiterpene derivatives (1 and 2), ramarin A (1) and ramarin B (2), together with three known compounds (3-5) were isolated from the fruiting bodies of Ramaria formosa. The structures of the two sesquiterpenes were established by extensive spectroscopic studies and chemical evidence. The inhibitory activity ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00051

    authors: Kim KC,Lee IS,Yoo ID,Ha BJ

    更新日期:2015-01-01 00:00:00

  • Development of a simple system for dehydrocondensation using solid-phase adsorption of a water-soluble dehydrocondensing reagent (DMT-MM).

    abstract::It has been indicated that hydrophilic solid powder to which aqueous solution of a novel dehydrocondensing reagent DMT-MM is adsorbed becomes a simple solid-phase dehydrocondensing reagent of low cost. Reaction in a liquid--liquid biphasic system on the surface of a solid phase with a large area was accelerated by sus...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1223

    authors: Watanabe Y,Fuji T,Hioki K,Tani S,Kunishima M

    更新日期:2004-10-01 00:00:00

  • Synthesis and pharmacological activity of 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4- pyrrolidinyl]benzamide (TKS159) and its optical isomers.

    abstract::Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1-ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, r...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1650

    authors: Yanagi T,Kitajima A,Anzai K,Kodama K,Mizoguchi J,Fujiwara H,Sakiyama H,Kamoda O,Kamei C

    更新日期:1999-11-01 00:00:00

  • An approach for decontamination of beta-lactam antibiotic residues or contaminants in the pharmaceutical manufacturing environment.

    abstract::An effective procedure for decontamination of beta-lactam antibiotic residues or contaminants in the pharmaceutical manufacturing environment was investigated. Decontamination with solutions of hydrochloric acid, sodium hydroxide, hydrogen peroxide and hydroxylamine as agents for degradation was assessed. According to...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1340

    authors: Fukutsu N,Kawasaki T,Saito K,Nakazawa H

    更新日期:2006-09-01 00:00:00

  • Inhibitory effects of perillosides A and C, and related monoterpene glucosides on aldose reductase and their structure-activity relationships.

    abstract::Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent type of inhibition of rat lens aldose reductase by perillosides A a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.920

    authors: Fujita T,Ohira K,Miyatake K,Nakano Y,Nakayama M

    更新日期:1995-06-01 00:00:00

  • New bicyclic taxane diterpenoids from Taxus sumatrana.

    abstract::Investigation of an acetone extract of the leaves and twigs of Taxus sumatrana has resulted in the isolation of two new bicyclic taxoids, tasumatrols M (1), and N (2) and a new baccatin III derivative, tasumatrol O (3) together with the previous known 7-deacetylcanadensene (4) and 2alpha,7beta,13alpha-triacetoxy-5alph...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.808

    authors: Shen YC,Hsu SM,Lin YS,Cheng KC,Chien CT,Chou CH,Cheng YB

    更新日期:2005-07-01 00:00:00

  • The practical synthesis of a uterine relaxant, bis(2-[[(2S)-2-([(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl]amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy]-N,N-dimethylacetamide) sulfate (KUR-1246).

    abstract::The synthetic route for a uterine relaxant, bis(2-[[(2S)-2-([(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl]amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy]-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1018

    authors: Yanagi T,Kikuchi K,Takeuchi H,Ishikawa T,Nishimura T,Yamamoto I

    更新日期:2001-08-01 00:00:00

  • A new gluco indole alkaloid, 3, 4-dehydro-5-carboxystrictosidine, from Peruvian Uña de Gato (Uncaria tomentosa).

    abstract::A new gluco indole alkaloid, 3,4-dehydro-5-carboxystrictosidine, was obtained from Peruvian Uña de Gato (Cat's Claw, original plant: Uncaria tomentosa) together with two known gluco indole alkaloids. This compound was the first example of isolation of a gluco monoterpenoid indole alkaloid having a 3,4-dihydro-beta-car...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1410

    authors: Kitajima M,Hashimoto K,Yokoya M,Takayama H,Aimi N,Sakai SI

    更新日期:2000-10-01 00:00:00

  • Decomposition of linear dodecylbenzenesulfonate by simultaneous treatment with ozone and ultraviolet irradiation: rapid disappearance of formed mutagens.

    abstract::The decomposition products and mutagenic activity in Salmonella typhimurium strains TA98, TA100 and TA104 in the presence and absence of S9 mix of linear dodecylbenzenesulfonate (DBS) in aqueous solution after ozone treatment alone or simultaneous treatment with ozone and ultraviolet (UV) irradiation (ozone/UV treatme...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1597

    authors: Murakami K,Matsumoto H,Kinouchi T,Ohnishi Y

    更新日期:1992-06-01 00:00:00

  • Synthesis and antibacterial activity of some imidazo[1,2-a]pyrimidine derivatives.

    abstract::A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The "in vitro" antibacterial activity of these compounds and their corresponding alpha-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1170

    authors: Rival Y,Grassy G,Michel G

    更新日期:1992-05-01 00:00:00

  • Metabolic fate of [14C]triglyceride-entrapped lactosylceramide-bearing liposomes after intravenous injection into mouse.

    abstract::We investigated the distribution and fate of liposomes after their intravenous injection into a mouse. Liposomes were composed of dimyristoylphosphatidylcholine, cholesterol and dicetylphosphate (7:2:1, molar ratio) with or without lactosylceramide. They were characterized as small unilamellar vesicles, approximately ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1016

    authors: Yoshioka S,Banno Y,Okano Y,Ohki K,Mizukami Y

    更新日期:1992-04-01 00:00:00

  • Three novel cantharidin-related compounds from the Chinese blister beetle, Mylabris phalerata Pall.

    abstract::Three novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.807

    authors: Nakatani T,Konishi T,Miyahara K,Noda N

    更新日期:2004-07-01 00:00:00

  • Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.

    abstract::Total synthesis of the biologically important axane sesquiterpenes, gleenol (1) and axenol (2), was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in exc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1606

    authors: Nakazaki A,Era T,Kobayashi S

    更新日期:2007-11-01 00:00:00

  • Hepatic calcium-binding protein regucalcin decreases Ca2+/calmodulin-dependent protein kinase activity in rat liver cytosol.

    abstract::The effect of regucalcin, a calcium-binding protein isolated from rat liver cytosol, on cytosolic Ca2+/calmodulin-dependent protein kinase activity was investigated. The increase in cytosolic Ca2+/calmodulin-dependent protein kinase activity with passage of incubation time was clearly prevented by the presence of regu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2216

    authors: Mori S,Yamaguchi M

    更新日期:1990-08-01 00:00:00

  • Effects of fatty acids, fatty amines and propylene glycol on rat stratum corneum lipids and proteins in vitro measured by fourier transform infrared/attenuated total reflection (FT-IR/ATR) spectroscopy.

    abstract::Fourier transform infrared/attenuated total reflection (FT-IR/ATR) spectroscopy was used to examine the effect of fatty acids, fatty amines and propylene glycol (PG) on the molecular mobility of rat stratum corneum lipids and keratinized proteins, using a hydrophobic solute, indomethacin, and a polar solute, 5- and 6-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1887

    authors: Takeuchi Y,Yasukawa H,Yamaoka Y,Kato Y,Morimoto Y,Fukumori Y,Fukuda T

    更新日期:1992-07-01 00:00:00

  • Study on colon-specific 5-Fu pH-enzyme Di-dependent chitosan microspheres.

    abstract::Colon-specific drug delivery systems (CDDS) can improve the bioavailability of drug through the oral route. A novel formulation for oral administration using pH-enzyme Di-dependent chitosan mcirospheres (MS) and 5-Fu as a model drug has been investigated for colon-specific drug delivery by the emulsification/chemical ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.963

    authors: Zhao XL,Li KX,Zhao XF,Pang DH,Chen DW

    更新日期:2008-07-01 00:00:00

  • Synthesis, crystal structure, and DNA-binding study on the trinitrate{2,2'-[2,3-naphthylenebis(oxy)]-bis(N,N-diisopropyl(acetamide))} gadolinium(III) complex.

    abstract::A 2,2'-[2,3-naphthylenebis(oxy)]-bis(N,N-diisopropyl(acetamide)) ligand (L) and its Gd(III) complex have been prepared and characterized. The crystal and molecular structure of the complex was determined by single-crystal X-ray diffraction. The interactions of complex with calf thymus DNA were investigated by UV-vis, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1150

    authors: Lei K,Liu W,Huang X,Wang D

    更新日期:2006-08-01 00:00:00

  • Physical characteristics of freeze-dried griseofulvin-lipids nanoparticles.

    abstract::We have attempted to prepare micronized drug particles and to maintain the micronized state long-term in order to improve the solubility of a practically insoluble drug, griseofulvin (GF). GF nanoparticles (GFNPs) prepared by high-pressure homogenization were micronized to about 45 nm (mean particle size). GFNPs were ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.181

    authors: Kamiya S,Nozawa Y,Miyagishima A,Kurita T,Sadzuka Y,Sonobe T

    更新日期:2006-02-01 00:00:00

  • Discovery of Novel 7-[(1R,5S)-1-Amino-5-fluoro-3-azabicyclo[3.3.0]octan-3-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropane]-8-(methoxy or methyl)quinolones.

    abstract::A series of 8-methoxy or 8-methylquinolones bearing novel 3-aminooctahydrocyclopenta[c]pyrrole derivatives at the C-7 position was synthesized, and the pharmacological, physicochemical, and toxicological properties of the individual compounds were evaluated. Novel 8-methylquinolone 7, which includes a 3-amino-7-fluoro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00671

    authors: Komoriya S,Odagiri T,Inagaki H,Nagamochi M,Miyauchi R,Yoshida KI,Kitamura T,Takahashi H

    更新日期:2019-01-01 00:00:00

  • High-performance liquid chromatographic determination of peptides released by tryptic degradation from opioid peptide precursors in rat brain.

    abstract::A high-performance liquid chromatographic method involving postcolumn fluorescence derivatization is described for the quantification of five fragment peptides (methionine-enkephalin-Thr-Ser-Glu-Lys, methionine-enkephalin-Lys, methionine-enkephalin-Arg, leucine-enkephalin-Lys and leucine-enkephalin-Arg) released by tr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2369

    authors: Zhang GQ,Kai M,Ohkura Y

    更新日期:1991-09-01 00:00:00