Synthesis of granulatimide positional analogues.

Abstract:

:The Stille coupling reaction of the stannylindole 13 with the 5-iodoimidazole derivative 14 (or 27) in the presence of PdCl(2)(PPh(3))(2) gave the corresponding indole-imidazole coupling product 15 (or 28), thereby affording a synthetic approach to 10-methylgranulatimide (7), 15-methylgranulatimide (11), and 10, 15-dimethylgranulatimide (12), as well as 10-methylisogranulatimide B (5).

authors

Yoshida T,Nishiyachi M,Nakashima N,Murase M,Kotani E

doi

10.1248/cpb.51.209

subject

Has Abstract

pub_date

2003-02-01 00:00:00

pages

209-14

issue

2

eissn

0009-2363

issn

1347-5223

journal_volume

51

pub_type

杂志文章
  • Megistoquinones I and II, two quinoline alkaloids with antibacterial activity from the bark of Sarcomelicope megistophylla.

    abstract::Two alkaloids, megistoquinone I (1) and megistoquinone II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data. Both belong to quinoline alkaloid series and should be considered as oxidation products of a furo[2,3-b]quinoline precursor. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.413

    authors: Fokialakis N,Magiatis P,Chinou I,Mitaku S,Tillequin F

    更新日期:2002-03-01 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

  • Highly spherical and deformable chitosan microspheres for arterial embolization.

    abstract::The aim of this study was to fabricate deformable chitosan (CS) microspheres for arterial embolization. CS microspheres containing poly(ethylene glycol) (PEG) were prepared by ionotropic gelation; PEG was then removed from the CS microspheres to produce the highly porous structure to allow deformability. The porosity ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.288

    authors: Kang MJ,Park JM,Choi WS,Lee J,Kwak BK,Lee J

    更新日期:2010-03-01 00:00:00

  • A stimulatory effect of Artemisia leaf extract on the proliferation of cultured endothelial cells.

    abstract::To investigate the effect of the hot water extract from Artemisia leaf (Artemisia princeps Panpanini) (AFE) on the proliferation of endothelial cells, the cells from bovine aorta were cultured for up to 96 h in the presence of 1, 5, 10 or 50 micrograms/ml AFE in RPMI1640 medium supplemented with 10% fetal bovine serum...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.538

    authors: Kaji T,Kaga K,Miezi N,Ejiri N,Sakuragawa N

    更新日期:1990-02-01 00:00:00

  • A new method to modify the C-4 position of 10-deacetylbaccatin III.

    abstract::We have developed a new method to modify the C-4 position of 10-deacetylbaccatin III (5) using the C-4 acetoxy anion of the 13-keto derivative (7) and various alkyl halides. The method developed herein should be very useful for the preparation of C-4 modified taxoid analogs. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.2093

    authors: Uoto K,Takenoshita H,Ishiyama T,Terasawa H,Soga T

    更新日期:1997-12-01 00:00:00

  • Cross-link dimer formation of the acetaldehyde-derived cyclic 1,N(2)-Propano-2'-deoxyguanosine adduct using electrochemical oxidation.

    abstract::The electrochemically oxidative lesion of the acetaldehyde-derived cyclic propano adduct 2 of 2'-deoxyguanosine 1 was identified as the cross-linked dimer 4 of adduct 2. Cross-link formation is explained by the nucleophilic preference of the exocyclic amino group in 2 to the carbocation 3 electrogenerated by 1-proton ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1434

    authors: Murakami H,Esaka Y,Uno B

    更新日期:2009-12-01 00:00:00

  • Antisweet natural products. VIII. Structures of hodulosides VI--X from Hovenia dulcis Thunb. var. tomentella Makino.

    abstract::From the Fresh leaves of Hovenia dulcis Thunb. var. tomentella Makino, five five new dammarane glycosides named hodulosides VI-X (1-5) were isolated. Their structures were determined on the basis of chemical and spectral evidence. Hodulosides VII-X showed antisweet activities. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1722

    authors: Yoshikawa K,Nagai Y,Yoshida M,Arihara S

    更新日期:1993-10-01 00:00:00

  • Studies on the constituents of Mikania hirsutissima (Compositae).

    abstract::Two novel norhumulene-type sesquiterpenes, named mikaniahumulene I (1) and II (2) were isolated along with nine known compounds, seven kaurenic acid-type diterpenes (3-9), a coumarin (10) and a flavone (11), from the aerial parts of Mikania hirsutissima DC (Compositae). The structures of new norhumulenes were determin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1436

    authors: Ohkoshi E,Makino M,Fujimoto Y

    更新日期:1999-10-01 00:00:00

  • alpha,alpha-gem-Difluorination of alpha-(alkylthio)acetophenone derivatives with N-fluoropyridinium salts.

    abstract::The alpha,alpha-gem-difluorination of 2',4'-difluoro-alpha-(methylthio)acetophenone (1a) with N-fluoropyridinium salts gave 2',4',alpha,alpha-tetrafluoro-alpha-(methylthio)acetophenone (3a). This reaction was accelerated by the addition of zinc chloride, zinc bromide or anhydrous iron(III) chloride, and higher yields ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1097

    authors: Takeda S,Kaneko Y,Eto H,Tokizawa M,Sato S,Yoshida K,Namiki S,Ogawa M

    更新日期:2000-07-01 00:00:00

  • Spectroscopic, thermal and biological studies of the coordination compounds of sulfasalazine drug: Mn(II), Hg(II), Cr(III), ZrO(II), VO(II) and Y(III) transition metal complexes.

    abstract::The complexations of sulfasalazine (H3Suz) with some of transition metals have been investigated. Three types of complexes, [Mn(HSuz)-2(H2O)4] x 2H2O, [M(HSuz)-2(H2O)2] x xH2O (M=Hg(II), ZrO(II) and VO(II), x=4, 8 and 6, respectively) and [M(HSuz)-2(Cl)(H2O)3] x xH2O (M=Cr(III) and Y(III), x=5 and 6, respectively) wer...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1585

    authors: El-Wahed MG,Refat MS,El-Megharbel SM

    更新日期:2008-11-01 00:00:00

  • Platinum and palladium complexes containing ethylenediamine derivatives as carrier ligands and their antitumor activity.

    abstract::We prepared new antitumor active platinum complexes containing N,N'-bis(2-chloroethyl)ethylenediamine (ClEn) as an alkylating carrier ligand in order to obtain increased antitumor effects. Some of the platinum complexes synthesized showed enhanced antitumor activity. However, palladium(II) complexes containing ClEn we...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.702

    authors: Lee K,Tashiro T,Noji M

    更新日期:1994-03-01 00:00:00

  • Synthesis and evaluation of (piperidinomethylene)bis(phosphonic acid) derivatives as anti-osteoporosis agents.

    abstract::Some (piperidinomethylene)bis(phosphonic acid) derivatives were prepared and their activity to inhibit a rise in serum calcium induced by parathyroid hormone in thyroparathyroidectomised rats was evaluated. Several (4-alkylidene-, 4,4-dialkyl-, or 4-alkyl-4-halopiperidinomethylene)bis(phosphonic acid) derivatives show...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1971

    authors: Mimura M,Hayashida M,Nomiyama K,Ikegami S,Iida Y,Tamura M,Hiyama Y,Ohishi Y

    更新日期:1993-11-01 00:00:00

  • Studies on the synthesis of compounds related to adenosine 3',5'-cyclic phosphate. VII. Synthesis and cardiac effects of N6,N6-dialkyl adenosine 3',5'-cyclic phosphates.

    abstract::A series of novel N6,N6-dialkyl adenosine 3',5'-cyclic phosphates N6,N6-dialkyl cAMPs) was synthesized from 2'-O-p-toluenesulfonyl cAMP (2'-O-tosyl cAMP, 2) and tested for inotropic and chronotropic activities in vitro. Treatment of 2 with excess alkyl halides and sodium hydride followed by detosylation with aqueous N...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.3147

    authors: Kataoka S,Yamaji N,Kato M,Kawada T,Imai S

    更新日期:1990-11-01 00:00:00

  • Study on the cell wall skeleton derived from Mycobacterium bovis BCG Tokyo 172 (SMP-105): establishment of preparation and analytical methods.

    abstract::Mycobacterial cell walls have diverse adjuvant activities, and in particular, cell wall skeleton (CWS) of Mycobacterium bovis BCG has been expected as a drug for tumor immunotherapy. However, its molecular structure-biological activity relationship has not been fully elucidated despite more than 30 years of intensive ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.843

    authors: Uenishi Y,Okada T,Okabe S,Sunagawa M

    更新日期:2007-06-01 00:00:00

  • Comparative pharmacokinetics of acetohexamide and its metabolite, hydroxyhexamide in laboratory animals.

    abstract::The pharmacokinetic profiles of the hypoglycemic agent, acetohexamide (AH) and its major active metabolite, hydroxyhexamide (HH) were studied in three species of laboratory animals after intraperitoneal (ipl) administration in comparison with those after intravenous (iv) administration of AH and of the preformed metab...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.760

    authors: Asada S,Nagamine S,Nakae H

    更新日期:1989-03-01 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

  • Cucurbitane triterpenoids from Momordica charantia and their cytoprotective activity in tert-butyl hydroperoxide-induced hepatotoxicity of HepG2 cells.

    abstract::Two novel pentanorcucurbitane triterpenes, 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one (1) and 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid (2) together with a new trinorcucurbitane triterpene, 25,26,27-trinorcucurbit-5-ene-3,7,23-trione (3) were isolated from the methyl alcohol extract of the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1639

    authors: Chen CR,Liao YW,Wang L,Kuo YH,Liu HJ,Shih WL,Cheng HL,Chang CI

    更新日期:2010-12-01 00:00:00

  • Two cangorosin A type triterpene dimers from Maytenus chuchuhuasca.

    abstract::Two new cangorosin A type triterpene dimers, which composed of two triterpene units jointed by two ether linkages between the A and B rings, were isolated from the Brazilian medicinal plant "xuxuá" (Maytenus chuchuhuasca). Structures of new isolates, xuxuasins A (1) and B (2), were established based on several spectro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.1148

    authors: Shirota O,Sekita S,Satake M,Morita H,Takeya K,Itokawa H

    更新日期:2004-09-01 00:00:00

  • In vitro transport of sodium diclofenac across rat abdominal skin: effect of selection of oleaginous component and the addition of alcohols to the vehicle.

    abstract::The in vitro percutaneous transport of sodium diclofenac from various oil vehicles was examined using rat abdominal skin as a model skin membrane. The overall transport of diclofenac through the skin from the oleaginous vehicles was very poor because of a poor solubility of sodium diclofenac in nonpolar oils. To incre...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.154

    authors: Takahashi K,Tamagawa S,Katagi T,Yoshitomi H,Kamada A,Rytting JH,Nishihata T,Mizuno N

    更新日期:1991-01-01 00:00:00

  • Aglaiabbrevins A-D, New Prenylated Bibenzyls from the Leaves of Aglaia abbreviata with Potent PTP1B Inhibitory Activity.

    abstract::Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl]bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were eluci...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00868

    authors: Sun P,Jiang CS,Zhang Y,Liu AH,Liang TJ,Li J,Guo YW,Jiang JM,Mao SC,Wang B

    更新日期:2017-01-01 00:00:00

  • Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.

    abstract::First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00138

    authors: Qian S,Chen QL,Guan JL,Wu Y,Wang ZY

    更新日期:2014-01-01 00:00:00

  • Release kinetics of nicotinamide from fatty acid-nicotinamide equimolar complexes. II. Activation thermodynamic quantities.

    abstract::The rates of release of nicotinamide (NAA) from fatty acid (FA)-NAA complexes, FA-NAA, were determined at various temperatures, and the thermodynamic quantities for the release of NAA were estimated. The results were compared with the previous results obtained for FA-thiamine disulfide (TDS) complexes, (FA)6(TDS). The...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3114

    authors: Yokoyama S,Ueda F,Fujie T

    更新日期:1991-12-01 00:00:00

  • Bilayer Tablet Dissolution Kinetics Based on a Degassing Cyclic Flow UV-Vis Spectroscopy with Chemometrics.

    abstract::Dissolution kinetics of a bilayer direct compress tablet was evaluated by using degassing cyclic flow UV-visible (Vis) spectroscopy with chemometrics. The model bilayer nicotinamide (NA)-pyridoxine hydrochloride (PH) 100.0 mg tablets were prepared via the dual compress method. The fast diffusion layer of the bilayer t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00867

    authors: Otsuka Y,Ito A,Takahashi T,Matsumura S,Takeuchi M,Tanaka H

    更新日期:2019-01-01 00:00:00

  • Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-joki-to.

    abstract::Prolyl endopeptidase (PEP, EC 3.4.21.26) is an enzyme playing a role in the metabolism of proline-containing neuropeptides which have been suggested to be involved in learning and memory processes. In screening for PEP inhibitors from fourteen traditional Kampo formulas, we found that Tokaku-joki-to shows a significan...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1055

    authors: Fan W,Tezuka Y,Kadota S

    更新日期:2000-07-01 00:00:00

  • Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica.

    abstract::The CHCl3 extract of the root of Angelica japonica showed high inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. From this extract, a new furanocoumarin named japoangelone and four furanocoumarin ethers of falcarindiol, named japoangelols A-D, were isolated together with caffeic acid methyl ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.96

    authors: Fujioka T,Furumi K,Fujii H,Okabe H,Mihashi K,Nakano Y,Matsunaga H,Katano M,Mori M

    更新日期:1999-01-01 00:00:00

  • Mechanistic study of electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzaldehyde in the presence of 3-hydroxy-1H-phenalene-1-one.

    abstract::The mechanism of the electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzaldehyde in the presence of 3-hydroxy-1H-phenalene-1-one as a nucleophile has been studied in water/acetonitrile (80/20 v/v) solution using cyclic voltammetry and controlled-potential coulometry methods. The results indica...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.513

    authors: Nematollahi D,Amani A

    更新日期:2008-04-01 00:00:00

  • A novel, bio-reducible gene vector containing arginine and histidine enhances gene transfection and expression of plasmid DNA.

    abstract::We have engineered a novel, non-viral, multifunctional gene vector (STR-CH(2)R(4)H(2)C) that contained stearoyl (STR) and a block peptide consisting of Cys (C), His (H), and Arg (R). STR-CH(2)R(4)H(2)C can form a stable nano-complex with plasmid DNA (pDNA) based on electronic interactions and disulfide cross linkages....

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.202

    authors: Tanaka K,Kanazawa T,Ogawa T,Suda Y,Takashima Y,Fukuda T,Okada H

    更新日期:2011-01-01 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

  • In Vitro Antitrypanosomal Activity of the Secondary Metabolites from the Mutant Strain IU-3 of the Insect Pathogenic Fungus Ophiocordyceps coccidiicola NBRC 100683.

    abstract::During the search for new antitrypanosomal drug leads, four antitrypanosomal compounds, of three depsipeptides and one nortriterpenoid, were isolated from cultures of the mutant strain IU-3 of the insect pathogenic fungus Ophiocordyceps coccidiicola NBRC 100683. Their structures were identified by the analysis of high...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00220

    authors: Ganaha M,Yoshii K,Ōtsuki Y,Iguchi M,Okamoto Y,Iseki K,Ban S,Ishiyama A,Hokari R,Iwatsuki M,Otoguro K,Ōmura S,Hashimoto T,Noji M,Umeyama A

    更新日期:2016-01-01 00:00:00

  • Hydrophobicity parameters determined by reversed-phase liquid chromatography. XVI: A new hydrogen-accepting parameter for monosubstituted thiophenes and furans for correlating retention factors and octanol-water partition coefficients.

    abstract::We recently proposed a new hydrogen-accepting parameter, S(HA), for monosubstituted (di)azines on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, S(HA) values for monosubstituted thiophenes and furans were calculated and the results were applied to the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1196

    authors: Yamagami C,Tachikawa H

    更新日期:2003-10-01 00:00:00