One-pot N-arylation of indoles directly from N-arylsulfonylindoles via consecutive deprotection and S(N)Ar Reactions with activated Aryl halides.

Abstract:

:An efficient one-pot step by step t-BuOK-mediated procedure for the synthesis of N-arylindoles has been developed in moderate to good yields. The protocol involves the consecutive deprotection of N-arylsulfonylindoles as latent indoles and subsequent S(N)Ar reactions with activated aryl halides. This tandem reaction affords an efficient and convenient preparation of N-arylindoles that benefit from prior indoles protection by arylsulfonyl group, and can shorten a reaction sequence and improve synthetic efficiency.

authors

Xu H,Fan LL

doi

10.1248/cpb.57.321

subject

Has Abstract

pub_date

2009-03-01 00:00:00

pages

321-3

issue

3

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/57.321

journal_volume

57

pub_type

杂志文章
  • Medicinal flowers. XI. Structures of new dammarane-type triterpene diglycosides with hydroperoxide group from flower buds of Panax ginseng.

    abstract::Six new dammarane-type triterpene diglycosides with a hydroperoxide group, floralginsenosides A, B, C, D, E, and F, were isolated from ginseng flower, the flower buds of Panax ginseng C. A. MEYER, together with seven known dammarane-type triterpene oligoglycosides. The structures of new floralginsenosides were elucida...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.571

    authors: Yoshikawa M,Sugimoto S,Nakamura S,Matsuda H

    更新日期:2007-04-01 00:00:00

  • Chemical Synthetic Platform for Chlorpromazine Oligomers That Were Reported as Photo-degradation Products of Chlorpromazine.

    abstract::A synthetic platform for chlorpromazine (CPZ) oligomers, which could be generated via photo-reaction of CPZ, is essential to promote their biological and structural studies. In this paper, the first synthetic platform for CPZ oligomers is described. A photo-irradiation experiment of CPZ to confirm whether the structur...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00692

    authors: Kohiki T,Nishikawa Y,Inokuma T,Shigenaga A,Otaka A

    更新日期:2017-01-01 00:00:00

  • NF-κB inhibitory activities of glycosides and alkaloids from Zanthoxylum schinifolium stems.

    abstract::Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract o...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00759

    authors: Li W,Yang SY,Yan XT,Sun YN,Song SB,Kang HK,Kim YH

    更新日期:2014-01-01 00:00:00

  • Multiple solubility maxima of oxolinic acid in mixed solvents and a new extension of Hildebrand solubility approach.

    abstract::A new extension of the Hildebrand solubility approach which describes drug solubility in solvent mixtures showing multiple solubility peaks, the chameleonic effect, is proposed. The experimental solubilities of oxolinic acid were measured at 25 degrees C in solvent mixtures of ethanol-water and ethanol-ethyl acetate. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.175

    authors: Jouyban-Gharamaleki A,Romero S,Bustamante P,Clark BJ

    更新日期:2000-02-01 00:00:00

  • Synthesis and affinities for dopamine (D2) and 5-hydroxytryptamine (5-HT2A) receptors of 1-(benzoylpropyl)-4-(1-oxocycloalkyl-2-ethyl)-piperazines as cyclic butyrophenone derivatives.

    abstract::Starting from benzo- or thienocycloalkaneacetic acids, we have prepared a series of 1-(3-p-fluorobenzoylpropyl)-4-(1-oxo-benzo- or thienocycloalkyl-2-ethyl)piperazines 8a-e containing both semirigid and linear butyrophenones pharmacophores. The affinities of these compounds for dopamine (D2) and 5-hydroxytryptamine (5...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.534

    authors: Raviña E,Fueyo J,Masaguer CF,Negreira J,Cid J,Loza I,Honrubia A,Tristán H,G-Ferreiro T,Fontenla JA,Rosa E,Calleja JM,De Ceballos ML

    更新日期:1996-03-01 00:00:00

  • Screening and Characterization of Hydrate Forms of T-3256336, a Novel Inhibitor of Apoptosis (IAP) Protein Antagonist.

    abstract::Different crystal packing of hydrates from anhydrate crystals leads to different physical properties, such as solubility and stability. Investigation of the potential of varied hydrate formation, and understanding the stability in an anhydrous/hydrate system, are crucial to prevent an undesired transition during the m...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00262

    authors: Takeuchi S,Kojima T,Hashimoto K,Saito B,Sumi H,Ishikawa T,Ikeda Y

    更新日期:2015-01-01 00:00:00

  • New acetylenic glucosides from Carthamus tinctorius.

    abstract::Two new acetylenic glucosides, 4',6'-acetonide-8Z-decaene-4,6-diyne-1-O-beta-D-glucopyranoside named carthamoside A(1) (1) and 4,6-decadiyne-1-O-beta-D-glucopyranoside named carthamoside A(2) (2), along with one known acetylenic glucoside, 8Z-decaene-4,6-diyne-1-O-beta-D-glucopyranoside (3), have been isolated from th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1455

    authors: Zhou YZ,Ma HY,Chen H,Qiao L,Yao Y,Cao JQ,Pei YH

    更新日期:2006-10-01 00:00:00

  • Development and validation of LC-MS/MS method for the quantification of oxcarbazepine in human plasma using an experimental design.

    abstract::A rapid tandem mass spectrometric (MS-MS) method for the quantification of Oxcarbazepine (OXB) in human plasma using imipramine as an internal standard (IS) has been developed and validated. Chromatographic separation was achieved isocratically on a C18 reversed-phase column within 3.0 min, using a mobile phase of ace...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.28

    authors: Srinubabu G,Ratnam BV,Rao AA,Rao MN

    更新日期:2008-01-01 00:00:00

  • Curcumin Inhibits Chondrocyte Hypertrophy of Mesenchymal Stem Cells through IHH and Notch Signaling Pathways.

    abstract::Using tissue engineering technique to repair cartilage damage caused by osteoarthritis is a promising strategy. However, the regenerated tissue usually is fibrous cartilage, which has poor mechanical characteristics compared to hyaline cartilage. Chondrocyte hypertrophy plays an important role in this process. Thus, i...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00225

    authors: Cao Z,Dou C,Dong S

    更新日期:2017-01-01 00:00:00

  • Cimiracemoside a: A new cyclolanostanol xyloside from the rhizome of Cimicifuga racemosa.

    abstract::A new 9,19-cyclolanostane-type triterpene xyloside (1), from the rhizomes of Cimicifuga racemosa, has been isolated together with four known saponins; cimiaceroside A, 25-O-methylcimigenol-3-O-beta-D-xylopyranoside, 27-deoxyactein and 23-O-acetylshengmanol-3-O-beta-D-xylopyranoside. The structure of the new compound w...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.425

    authors: Bedir E,Khan IA

    更新日期:2000-03-01 00:00:00

  • Transport to intestinal lumen and peritoneal cavity of intravenously administered aprinidine in rats.

    abstract::Transfer of aprindine from the blood into the intestinal lumen or into the peritoneal cavity was examined after intravenous administration of the drug at a dose of 5 mg/kg in rats. The amount of the drug transferred from the blood into the intestinal lumen was much greater than into the peritoneal cavity. The average ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3359

    authors: Arimori K,Hashimoto Y,Nakano M

    更新日期:1991-12-01 00:00:00

  • Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.

    abstract::The Michael reaction of malonates with maleates afforded the corresponding adducts in high yields with high enantioselectivities (up to 98% enantiomeric excess (ee)) by using dilithium 3,3'-dichlorobinaphtholate as a catalyst. The obtained Michael adducts could be converted to optically active tricarboxylic acid (TCA)...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00993

    authors: Sakamoto M,Kaneko T,Orito Y,Shimoda Y,Nakajima M

    更新日期:2019-01-01 00:00:00

  • Syntheses of cerulenin and its analogs. II. Synthesis and biological activity of dl-carbacerulenin, a carbocyclic analog of cerulenin.

    abstract::2,3-Epoxy-4-hydroxy-4-((E,E)-3,6-octadienyl)cyclopentanone (dl-carbacerulenin 5) was synthesized via the epoxyketones 15a and 15b as a mimic of the active form of the antibiotics cerulenin 1, a potent inhibitor of fatty acid synthetase (FAS). The monobenzyl ethers (12 and 13), synthetic intermediates of 15, were prepa...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2954

    authors: Shimazawa R,Ogawa Y,Morisaki N,Funabashi H,Kawaguchi A,Iwasaki S

    更新日期:1992-11-01 00:00:00

  • Solubility behavior and prediction for antihelmintics at several temperatures in aqueous and nonaqueous mixtures.

    abstract::A model based on solubility parameters is proposed to predict the solubility curves of antihelmintic drugs at several temperatures, including aqueous and non-aqueous mixtures. The solubility of the drugs was measured in ethanol-water and ethanol-ethyl acetate mixtures at 15-35 degrees C (mebendazole) and at 25 degrees...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.644

    authors: Bustamante P,Muela S,Escalera B,Peña A

    更新日期:2010-05-01 00:00:00

  • The complete amino acid sequence of an abortifacient protein, karasurin.

    abstract::The complete amino acid sequence of a new abortifacient protein, karasurin, was determined. Karasurin, which was isolated from fresh root tubers of Trichosanthes kirilowii Maximowicz var, japonicum Kitamura (Cucurbitaceae), was a highly basic protein with pI 10.1 and molecular weight of 28,000. Intact karasurin was cl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1244

    authors: Toyokawa S,Takeda T,Kato Y,Wakabayashi K,Ogihara Y

    更新日期:1991-05-01 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

  • Constituents of Crinoidea. 5. Isolation and structure of a new glycosyl inositolphosphoceramide-type ganglioside from the feather star Comanthina schlegeli.

    abstract::A new glycosyl inositolphosphoceramide-type ganglioside, CSP2, was obtained from the polar lipid fraction of the chloroform/methanol extract of the feather star Comanthina schlegeli together with a known same type of ganglioside CJP2. The structure of this ganglioside has been determined on the basis of chemical and s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1649

    authors: Inagaki M,Shiizaki M,Hiwatashi T,Miyamoto T,Higuchi R

    更新日期:2007-11-01 00:00:00

  • Light irradiation is a factor in the bactericidal activity of silver-loaded zeolite.

    abstract::Silver loaded zeolite (Ag-Z) was previously found to have effective bactericidal activity against Escherichia coli. To understand the mechanisms of bactericidal activity of Ag-Z, role of light irradiation was focused and investigated in this study. In this study, we focused on light irradiation. Antibacterial assay an...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.692

    authors: Inoue Y,Kogure M,Matsumoto K,Hamashima H,Tsukada M,Endo K,Tanaka T

    更新日期:2008-05-01 00:00:00

  • (2+2) cycloaddition reaction of alkyl enol ethers with acrylates by in situ generated silyl triflic imide catalyst.

    abstract::We describe here (2+2) cycloaddition reaction of alkyl enol ethers with acrylates catalyzed by triethylsilyl triflic imide (Et3SiNTf2), which was in situ generated from triethylsilane and triflic imide. The reaction efficiently provides substituted cyclobutanes bearing alkoxy function in a stereoselective manner. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1205

    authors: Takasu K,Miyakawa Y,Ihara M,Tokuyama H

    更新日期:2008-08-01 00:00:00

  • Vanadate-stimulated release of hepatic lipase activity from liver.

    abstract::Vanadate stimulated the release of rat hepatic lipase activity from liver slices into an incubation medium in a time- and dose-dependent manner. Insulin, however, failed to have this stimulatory action, and the release by heparin was recognized, but was not additive to that by vanadate. Amiloride, an inhibitor of tyro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3287

    authors: Morita T,Mikami F,Kanagawa A,Sera M,Ueki H

    更新日期:1991-12-01 00:00:00

  • Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine.

    abstract::α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00130

    authors: Li Z,Kumagai N,Shibasaki M

    更新日期:2020-01-01 00:00:00

  • Studies on cardiotonic agents. IV. Synthesis of novel 1-(6,7-dimethoxy-4-quinazolinyl)piperidine derivatives carrying substituted hydantoin and 2-thiohydantoin rings.

    abstract::A series of novel 1-(6,7-dimethoxy-4-quinazolinyl)piperidines carrying substituted hydantoin and 2-thiohydantoin rings was synthesized and examined for cardiotonic activity in anesthetized dogs. Introduction of isopropyl and sec-butyl group at the 5-position of the hydantoin and thiohydantoin rings led to potent inotr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.3014

    authors: Nomoto Y,Takai H,Hirata T,Teranishi M,Ohno T,Kubo K

    更新日期:1990-11-01 00:00:00

  • Solution-phase automated synthesis of tripeptide derivatives.

    abstract::An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, di...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1138

    authors: Kuroda N,Hattori T,Kitada C,Sugawara T

    更新日期:2001-09-01 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

  • Phenylethanoid and iridoid glycosides in the New Zealand snow hebes (Veronica, Plantaginaceae).

    abstract::Snow hebes are the alpine cushion-forming plants of New Zealand Veronica, formerly classified as Chionohebe. The chemical compositions of Veronica pulvinaris and Veronica thomsonii were studied and 33 water-soluble compounds were isolated. The structures of 14 previously unknown esters of phenylethanoid glycosides wer...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.703

    authors: Taskova RM,Kokubun T,Ryan KG,Garnock-Jones PJ,Jensen SR

    更新日期:2010-05-01 00:00:00

  • Stomach-site specific drug delivery system of clarithromycin for eradication of Helicobacter pylori.

    abstract::Gellan gum based floating beads containing clarithromycin (FBC) were prepared by iontotropic gelation method for stomach-specific drug delivery against Helicobacter pylori. The scanning electron microscope photograph indicated that prepared beads were spherical in shape with rough outer surface. Formulation variables ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1068

    authors: Rajinikanth PS,Mishra B

    更新日期:2009-10-01 00:00:00

  • Paracetamol-propyphenazone interaction and formulation difficulties associated with eutectic formation in combination solid dosage forms.

    abstract::Polymorphic behaviours of paracetamol and propyphenazone and interaction between these two compounds were investigated using differential scanning calorimetry (DSC), X-ray powder diffraction and Fourier transform-infrared (FT-IR)-spectroscopy. Binary mixtures containing various ratios of the compounds were prepared as...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.302

    authors: Zalac S,Khan MZ,Gabelica V,Tudja M,Mestrović E,Romih M

    更新日期:1999-03-01 00:00:00

  • Preparation of 9-hydroxy grayanotoxin derivatives and their acute toxicity in mice.

    abstract::Novel 9alpha and 9beta-hydroxy grayanotoxin II derivatives were prepared by photo-sensitized oxygenation of iso-grayanotoxin II and oxidation of grayanotoxin II tetraacetate with selenium dioxide respectively. The lethal dosage of 9alpha and 9beta-hydroxy grayanotoxin II were lower than that of grayanotoxin II. In add...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.351

    authors: Terai T,Osakabe K,Katai M,Sakaguchi K,Narama I,Matsuura T,Katakawa J,Tetsumi T

    更新日期:2003-03-01 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

  • Dissociation of DNA from histone by reaction of anti-cancer drug cis-diamminedichloroplatinum(II) with DNA-histone complexes used as cellular model.

    abstract::Although both cis-diamminedichloroplatinum(II) (cisplatin or cis-DDP) and trans-diamminedichloroplatinum(II) bind to DNA, only cis-DDP is widely used as a chemotherapeutic agent; the stereoisomer trans-DDP is inactive. DNA, generally, is wound around the histone core in the nucleus of living cells and forms the nucleo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.520

    authors: Koyama Y,Kikuchi S,Nakagawa S,Kobayashi S

    更新日期:2007-04-01 00:00:00