Pericyclic reaction of ketenes with cascade reaction products of pyridine N-oxides and dipolarophiles. X-ray structures of the adducts and formation mechanism.

Abstract:

:The structures of the adducts derived from the reactions of substituted ketenes with dihydropyridine derivatives have been clarified by single crystal X-ray analyses and the formation mechanism is discussed on the basis of the reaction-path calculations by semiempirical and density functional theory (DFT) molecular orbital methods.

authors

Oiso S,Eto M,Yoshitake Y,Harano K

doi

10.1248/cpb.51.1068

subject

Has Abstract

pub_date

2003-09-01 00:00:00

pages

1068-74

issue

9

eissn

0009-2363

issn

1347-5223

journal_volume

51

pub_type

杂志文章
  • Chemical constituents of the bulbs of Habranthus brachyandrus and their cytotoxic activities.

    abstract::The bulbs of Habranthus brachyandrus (Amaryllidaceae) have been extensively analyzed for their chemical constituents, resulting in the isolation of eight flavan derivatives (1-8), four of which are new naturally occurring compounds; a new hydroxybutyric acid glucoside (9); three known phenolic compounds (10-12); and s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1153

    authors: Jitsuno M,Yokosuka A,Sakagami H,Mimaki Y

    更新日期:2009-10-01 00:00:00

  • Synthesis, in Vivo Anti-inflammatory, and in Vitro Antimicrobial Activity of New 5-Benzofuranyl Fused Pyrimidines.

    abstract::Chalcone (3) has been synthesized as a new chalcone derivative bearing benzofuran moiety at 1 position. Such chalcone was used as a model dielectrophile applied to react with some nucleophiles such as 5-amino pyrazoles, 5-amino-1,2,4-triazole, 2-aminobenzimidazole, and 6-uraciles under Michael reaction conditions and ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00922

    authors: Nassar E,El-Badry YA,El Kazaz H

    更新日期:2016-01-01 00:00:00

  • Synthesis and antinociceptive activity of orally active opioid peptides: improvement of oral bioavailability by esterification.

    abstract::To improve the oral bioavailability of a dermorphin tetrapeptide analog, N(alpha)-1-iminoethyl-Tyr-D-MetO-Phe-MebetaAla-OH (III), which has a potent analgesic activity after oral administration, various derivatives were synthesized to increase lipophilicity by esterification of the C-terminal carboxyl group and/or acy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.759

    authors: Ogawa T,Araki M,Miyamae T,Okayama T,Hagiwara M,Sakurada S,Morikawa T

    更新日期:2003-07-01 00:00:00

  • Photoinduced upregulation of calcitonin gene-related peptide in A549 cells through HNO release from a hydrophilic photocontrollable HNO donor.

    abstract::Nitroxyl (HNO), a one-electron-reduced form of nitric oxide, has various biological activities, including a cardioprotective effect. Here, we first synthesized another, more hydrophilic photocontrollable HNO donor (3), which can release HNO in a spatially and temporally controlled manner, and then examined the propert...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00348

    authors: Matsuo K,Nakagawa H,Adachi Y,Kameda E,Aizawa K,Tsumoto H,Suzuki T,Miyata N

    更新日期:2012-01-01 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

  • Enzyme immunoassay for the drug of anti-ulcer using avidin-biotin system.

    abstract::We have developed a competitive enzyme immunoassay for a drug, which was a newly synthesized anti-ulcer agent, using an enzyme immunoassay. The polyclonal anti-drug antibody coupled to biotin, peroxidase labeled drug derivatives as a tracer, and a small column of Sepharose 4B covalently bound to avidin were used in th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1779

    authors: Okumura T,Asano T,Adachi T,Hirano K

    更新日期:1991-07-01 00:00:00

  • Stability of Mixed Preparations Consisting of Commercial Moisturizing Creams with an Ointment Base Investigated by Magnetic Resonance Imaging.

    abstract::A moisturizing cream mixed with a steroid ointment is frequently prescribed to patients suffering from atopic dermatitis. However, there is a concern that the mixing operation causes destabilization. The present study was performed to investigate the stability of such preparations closely using magnetic resonance imag...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00986

    authors: Onuki Y,Funatani C,Yamamoto Y,Fukami T,Koide T,Hayashi Y,Takayama K

    更新日期:2017-01-01 00:00:00

  • Two new C21 steroidal glycosides from Marsdenia tenacissima (ROXB.) WIGHT et ARN.

    abstract::Two new C(21) steroidal glycosides, tenacissoside L (1), tenacissoside M (2), were isolated from the stems of Marsdenia tenacissima (ROXB.) WIGHT et ARN. Their structures were elucidated, respectively, by means of chemical and spectral data, including ESI-MS, HR-ESI-MS, 1D-NMR and 2D-NMR. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.696

    authors: Wang S,Lai YH,Tian B,Yang L

    更新日期:2006-05-01 00:00:00

  • Studies on novel bone resorption inhibitors. I. Synthesis and pharmacological activities of aminomethylenebisphosphonate derivatives.

    abstract::A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalcemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investig...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.688

    authors: Takeuchi M,Sakamoto S,Yoshida M,Abe T,Isomura Y

    更新日期:1993-04-01 00:00:00

  • Slow release of tetracycline from a mucoadhesive complex with sucralfate for eradication of Helicobacter pylori.

    abstract::Treatment composed of a gastric mucoadhesive antibiotic with slow release drug delivery is expected to be effective for the eradication of Helicobacter pylori (H. pylori). In this study, we evaluated the slow release property of the tetracycline-sucralfate acidic complex. Tetracycline was the antibiotic selected becau...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1412

    authors: Higo S,Takeuchi H,Yamamoto H,Hino T,Kawashima Y

    更新日期:2008-10-01 00:00:00

  • Application of the solid dispersion method to the controlled release of medicine. IV. Precise control of the release rate of a water soluble medicine by using the solid dispersion method applying the difference in the molecular weight of a polymer.

    abstract::Solid dispersions were prepared by the evaporation of ethanol after dissolving into ethanol a water soluble medicine (oxprenolol hydrochloride (OXP)), four grades of water insoluble ethylcellulose (EC) and four grades of water soluble hydroxypropyl cellulose (HPC), both having different molecular weights. The precise ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.933

    authors: Yuasa H,Ozeki T,Kanaya Y,Oishi K

    更新日期:1993-05-01 00:00:00

  • Chemical constituents of Tupistra chinensis rhizomes.

    abstract::A new pregnane glycoside, a dibenzylbutyrolactone lignan, 5-hydroxymatairesinol dimethyl ether, and three new flavonoids, including one 8-methylflavan-3-ol, and two 8-methylflavones, together with five known flavonoids and two known alkaloids were isolated from the rhizomes of Tupistra chinensis. The structures of all...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.954

    authors: Pan WB,Wei LM,Wei LL,Wu YC

    更新日期:2006-07-01 00:00:00

  • Design and synthesis of a novel water-soluble NMDA receptor antagonist with a 1,4,7,10-tetraazacyclododecane group.

    abstract::Polyamines, 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 st...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.444

    authors: Masuko T,Metori K,Kizawa Y,Kusama T,Miyake M

    更新日期:2005-04-01 00:00:00

  • Specific effect of polyunsaturated fatty acids on the cholesterol-poor membrane domain in a model membrane.

    abstract::To understand more fully the effect of polyunsaturated fatty acids (PUFAs) on lipid bilayers, we investigated the effects of treatment with fatty acids on the properties of a model membrane. Three kinds of liposomes comprising dipalmitoylphosphatidylcholine (DPPC), dioleylphosphatidylcholine (DOPC), and cholesterol (C...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1103

    authors: Onuki Y,Hagiwara C,Sugibayashi K,Takayama K

    更新日期:2008-08-01 00:00:00

  • Synthesis and pharmacological activities of novel bicyclic thiazoline derivatives as hepatoprotective agents. I. 8-Ethoxycarbonyl-5,6-dihydrothiazolo[2,3-c][1,4]thiazine derivatives.

    abstract::A series of bicyclic thiazoline derivatives (4a-s) was synthesized and evaluated for hepatoprotective activity against galactosamine-induced and monoclonal antibody-induced acute liver injuries in rats. The structure-activity relationships were investigated. Among the compounds synthesized, ethyl 3-(N-methylcarbamoyl)...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.78

    authors: Hasegawa M,Nakayama A,Hosokami T,Kurebayashi Y,Ikeda T,Shimoto Y,Ide S,Honda Y,Suzuki N

    更新日期:1995-01-01 00:00:00

  • Synthesis of cis-bicyclo[4.3.0]non-2-ene derivatives. The potent homoisocarbacyclin analogs.

    abstract::Synthesis of homoisocarbacyclin has been achieved efficiently by a general strategy with stereo- and regiochemical control. One of homoisocarbacyclin derivatives, 3-oxa homoisocarbacyclin analog (4), was shown to be potently active in inhibiting gastric ulcer. Another analog, conjugated diene derivative (5), was found...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1647

    authors: Shibasaki M,Takahashi A,Aoki T,Sato H,Narita S

    更新日期:1989-06-01 00:00:00

  • Contribution of prostaglandins to the renal responses to magnesium lithospermate B isolated from salviae miltiorrhizae radix.

    abstract::The involvement of prostanoids in the improvement of adenine-induced renal failure in rats by magnesium lithospermate B was studied. After intraperitoneal administration of magnesium lithospermate B to renal failure rats, the levels of glomerular filtration rate, renal plasma flow and renal blood flow were increased. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1568

    authors: Yokozawa T,Chung HY,Lee TW,Oura H,Tanaka T,Nonaka G,Nishioka I,Hirai A

    更新日期:1989-06-01 00:00:00

  • Sulfonic acid functionalized silica: an efficient heterogeneous catalyst for a three-component synthesis of 1,4-dihydropyridines under solvent-free conditions.

    abstract::Sulfonic acid functionalized silica catalyzed the three-component reaction of aromatic amines, alpha,beta-unsaturated aldehydes and beta-keto esters forming the corresponding 1,4-dihydropyridines in short reaction times and in high yields. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.366

    authors: Das B,Suneel K,Venkateswarlu K,Ravikanth B

    更新日期:2008-03-01 00:00:00

  • New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Uña de Gato" (Uncaria tomentosa).

    abstract::A new oleanan-type triterpene and three new cincholic acid glycosides were isolated from Peruvian "Una de Gato" (Cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1258

    authors: Kitajima M,Hashimoto K,Sandoval M,Aimi N,Takayama H

    更新日期:2004-10-01 00:00:00

  • Novel method to control release of lipophilic drugs with high potency from silicone.

    abstract::Silicone has been utilized as a carrier material for sustained release system of lipophilic drugs. Extensive studies revealed that drug release rate is influenced by factors such as physicochemical properties of the drug and additives.(1-5)) When a lipophilic drug is highly potent at low concentrations, the drug relea...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.11

    authors: Kajihara M,Sugie T,Sano A,Fujioka K,Urabe Y,Tanihara M,Imanishi Y

    更新日期:2003-01-01 00:00:00

  • Cytotoxic cardenolides from woods of Euonymus alata.

    abstract::Three cytotoxic cardenolides, acovenosigenin A 3-O-alpha-L-ramnopyranoside (1), euonymoside A (2) and euonymusoside A (3), were isolated from the woods of Euonymus alata (Celastraceae). The chemical structure of a new cardenolide, euonymusoside A (3) has been elucidated on the basis of extensive spectral analysis and ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.615

    authors: Kitanaka S,Takido M,Mizoue K,Nakaike S

    更新日期:1996-03-01 00:00:00

  • Two new acyclic diterpene glycosides from fruits of Habanero, Capsicum chinense.

    abstract::Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyran...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.730

    authors: Lee JH,El-Aasr M,Ikeda T,Oda K,Miyashita H,Yoshimitsu H,Okawa M,Kinjo J,Nohara T

    更新日期:2009-07-01 00:00:00

  • Effect of polymer excipients on the enzyme activity of lyophilized bilirubin oxidase and beta-galactosidase formulations.

    abstract::The effects of excipients on the protein stability during lyophilization as well as the storage stability of lyophilized bilirubin oxidase (BO) and beta-galactosidase (GA) formulations were studied using four polymer excipients: dextran, polyvinylalcohol (PVA), poly(acrylic acid) (PAA), and alpha, beta-poly(N-hydroxye...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.283

    authors: Yoshioka S,Aso Y,Kojima S,Tanimoto T

    更新日期:2000-02-01 00:00:00

  • Synthesis, Characterization and Antifungal Evaluation of Novel Thiochromanone Derivatives Containing Indole Skeleton.

    abstract::Invasive fungal disease constitutes a growing health problem and development of novel antifungal drugs with high potency and selectivity against new fungal molecular targets are urgently needed. In order to develop potent antifungal agents, a novel series of 6-alkyl-indolo[3,2-c]-2H-thiochroman derivatives were synthe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00366

    authors: Han XY,Zhong YF,Li SB,Liang GC,Zhou G,Wang XK,Chen BH,Song YL

    更新日期:2016-09-01 00:00:00

  • Bile salt-induced disintegration of egg phosphatidylcholine liposomes: a kinetic study based on turbidity changes.

    abstract::The disintegration kinetics of egg phosphatidylcholine small unilamellar liposomes in various bile salts (nine species) were investigated by monitoring turbidity changes with a stopped-flow apparatus. The pseudo-first-order rate constants obtained as a function of bile salt concentration (up to 25 mM) were analyzed ba...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1341

    authors: Nagata M,Yotsuyanagi T,Ikeda K

    更新日期:1990-05-01 00:00:00

  • Enzyme inhibitory constituents from Duranta repens.

    abstract::Isoprenylated flavonoids 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxyflavone (1), 3,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-5,6,4'-trimethoxyflavone (2) and an isoprenylated acetophenone derivative (3) have been isolated from Duranta repens along with known compounds, 5-hydroxy-3,6,7,4'-tetr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.515

    authors: Anis I,Ahmed S,Malik A,Yasin A,Choudary MI

    更新日期:2002-04-01 00:00:00

  • A novel method for estimation of transition temperature for polymorphic pairs in pharmaceuticals using heat of solution and solubility data.

    abstract::A novel method for thermodynamic stability studies of polymorphic drug substances has been developed. In order to estimate the transition temperature for an enantiotropic polymorphic pair, a formula for calculating the temperature at which the solubilities of each polymorph become equal has been derived with heat of s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.263

    authors: Urakami K,Shono Y,Higashi A,Umemoto K,Godo M

    更新日期:2002-02-01 00:00:00

  • Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring modified and 7,10-disubstituted camptothecins.

    abstract::20(S)-Camptothecin derivatives having nitro, amino, chloro, bromo, hydroxyl and methoxyl groups in the A-ring were synthesized. B-Ring hydrogenated camptothecin (2a) was converted into 10-hydroxycamptothecin (6e) by treatment with lead tetraacetate in trifluoroacetic acid. 10-Substituted derivatives (6) were obtained ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3183

    authors: Sawada S,Matsuoka S,Nokata K,Nagata H,Furuta T,Yokokura T,Miyasaka T

    更新日期:1991-12-01 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

  • Structure of three new carotenoids with a 3-methoxy-5-keto-5,6-seco-4,6-cyclo-beta end group from the seeds of Pittosporum tobira.

    abstract::Three new carotenoids with a 3-methoxy-5-keto-5,6-seco-4,6-cyclo-beta end group (1-3) have been isolated from the seeds of Pittosporum tobira. Their structures were elucidated by detailed analyses of nuclear magnetic resonance and UV data. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.985

    authors: Fujiwara Y,Maruwaka H,Toki F,Hashimoto K,Maoka T

    更新日期:2001-08-01 00:00:00