Abstract:
:A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Sugiyama S,Arai S,Kiriyama M,Ishii Kdoi
10.1248/cpb.53.100subject
Has Abstractpub_date
2005-01-01 00:00:00pages
100-2issue
1eissn
0009-2363issn
1347-5223pii
JST.JSTAGE/cpb/53.100journal_volume
53pub_type
杂志文章abstract::Stereocontrolled syntheses of model compounds related to a major antigenic epitope against antibupleurum 2IIc/PG-1-IgG from antiulcer pectic polysaccharide are described. A trisaccharide derivative (13) was prepared as a precursor and a novel and simple approach for the rational design of a glycocluster and glycodendr...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.54.485
更新日期:2006-04-01 00:00:00
abstract::From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.678
更新日期:2002-05-01 00:00:00
abstract::In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as α,β-dicarboxylic acid d...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.120
更新日期:2011-01-01 00:00:00
abstract::New antitumor alkylglycerophospholipids, in which primarily the phosphocholine moiety of the platelet activating factor (PAF) molecule was modified, were synthesized from 1-alkyl-2-substituted glycerols by introducing polar head phosphoryl groups having methylene bridges of various lengths (from 2 to 14 carbons). They...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.1249
更新日期:1989-05-01 00:00:00
abstract::To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1), (2RS,3SR)-2-benzoylamino-3-hydroxy-3-phenylpropanoic acid [(2RS,3SR)-2] was first optically resolved using (1S,2S)- and (1R,2R)-2-amino-1-(4-nitrophenyl)-1,3-propanediol as the resolving agents to afford (2R,3S)- and (2S,3R)-2 in yields of ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.1363
更新日期:2003-12-01 00:00:00
abstract::From Puerariae Radix, the root of Pueraria lobata (Leguminosae), six new oleanene-type triterpene glycosides, called kudzusaponins A1 (1), A2 (2), Ar (3), SA4 (5), and SB1 (6) were isolated together with kudzusaponin A3 (7), soyasaponins SA3 (8), and I (9). The structures of 1-6 were determined to be 3-O-alpha-L-rhamn...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.362
更新日期:1997-02-01 00:00:00
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
更新日期:2010-05-01 00:00:00
abstract::Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a dipeptide sweetener about 200 times as sweet as sugar. It exists in crystal forms such as IA, IB, IIA, and IIB, which differ in crystal structure and in the degree of hydration. Among these, IIA is the most stable crystal form, and its crystal structure ha...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.48.708
更新日期:2000-05-01 00:00:00
abstract::Four new triterpene glycosides, named nigellosides A, B, C, and D, were from the air-dried aerial parts of Nigella damascena L. (Ranunculaceae), and the structures were elucidated on the basis of spectroscopic data including 2D NMR spectra and chemical evidence. Their chemical structures have been characterized as 3-O...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.55.488
更新日期:2007-03-01 00:00:00
abstract::The direct conversion of alpha-hydroxy ketones and alpha-keto oximes into quinoxaline derivatives in the presence of a catalytic amount of ceric ammonium nitrate via metal-catalyzed aerobic oxidation followed by in situ trapping with aromatic 1,2-diamines in water as a green and efficient reaction media, is reported. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.79
更新日期:2008-01-01 00:00:00
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
更新日期:2009-12-01 00:00:00
abstract::Novel hybrid L-ascorbic acid (vitamin C) derivatives with other biologically active substances, 5-hydroxy-2-hydroxymethyl-beta-pyrone (kojic acid) and alpha-tocopherol (vitamin E), linked at the C-2 or C-3 hydroxyl group were synthesized, and their thermal stability and inhibitory effects on tyrosinase activity, activ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.44.1647
更新日期:1996-09-01 00:00:00
abstract::A novel C-methylated biflavone, taiwanhomoflavone-B (1), together with known compounds, 7,4',7"-tri-O-methylamentoflavone, 6-C-methylnaringenin and apigenin-7-O-beta-glucoside were isolated from an ethanolic extract of Cephalotaxus wilsoniana. The structure of 1 was elucidated on the basis of spectroscopic analysis. T...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.1607
更新日期:2002-12-01 00:00:00
abstract::An examination was made on the effect of fumaric acid on an experimental systemic candidiasis. Male ICR mice were innoculated into the tail veins with 10(6) yeast cells of Candida albicans and treated with daily intraperitoneal injections of fumaric acid at the dose of 40 mg/kg/d. The results indicated that the admini...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.39.3077
更新日期:1991-11-01 00:00:00
abstract::New gamma-pyrones, 9'-oxopodopyrone (3) and 8-methyl-9'-oxopodopyrone (4) were isolated from the leaves of Gonystylus keithii, along with known gamma-pyrones, 10'-oxopodopyrone (1) and 8-methyl-10'-oxopodopyrone (2). These gamma-pyrones markedly inhibited the bovine parathyroid hormone (PTH)-induced Ca release from ne...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.1046
更新日期:1997-06-01 00:00:00
abstract::Deacetylation of enynyl acetates under basic conditions allows convenient access to reactive allenyl ketones, which can then undergo 1,4-addition of nucleophiles to furnish β,γ-unsaturated ketones. Benzofuran and indole derivatives have also been obtained from enynyl acetates with an o-hetero-atom-substituted aryl gro...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c16-00170
更新日期:2016-01-01 00:00:00
abstract::Chemical investigation of the soft coral Sinularia leptoclados has afforded three new sesquiterpenoids, leptocladols A (1), B (2), and 1-epi-chabrolidione A (3). The relative structures of 1-3 were determined on the basis of extensive spectroscopic analysis. The relative configuration of 1 was further confirmed by a s...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.250
更新日期:2010-02-01 00:00:00
abstract::The constituents of the MeOH extract of Salvia miltiorhiza BUNGE, which showed strong aldose reductase (AR) inhibitory activity, were examined, and two new abietane-type diterpenoids, danshenol A (1) and danshenol B (2), were isolated together with six known ones: dihydrotanshimme I (3), cryptotanshinone (4), tanshino...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.1306
更新日期:1997-08-01 00:00:00
abstract::A series of benzylamides of N-alkylated, N-acylated or free nine cyclic and one linear amino acids as potential anticonvulsants have been synthesized. The structures of the obtained compounds were designed on the basis of the previously determined structure and physicochemical properties/anticvonvulsant activity relat...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.629
更新日期:2001-05-01 00:00:00
abstract::A new heptapeptide GAGPHGG (OC1) was isolated from Carapax trionycis which was a traditional Chinese medicine (TCM) used for treatment of hepatic diseases. The structure of OC1 was characterized by MS, NMR techniques, together with amino acid sequence analysis. The hepatoprotective activity of OC1 was evaluated in viv...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c13-00442
更新日期:2013-01-01 00:00:00
abstract::Simple one-pot methods for preparation of 2-oxazolines have been developed using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Treatment of a mixture of carboxylic acids and 2-haloethylammonium salts with DMT-MM in methanol followed by refluxing in the presence of KOH gives oxazolines. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1735
更新日期:2008-12-01 00:00:00
abstract::Several E-ring-modified analogues of (RS)-camptothecin were synthesized by total synthesis via Friedländer condensation and evaluated for cytotoxicity and antitumor activity against P388 mouse leukemia cells. Among them, (RS)-20-deoxyamino-7-ethyl-10-methoxycamptothecin (25c) was found to be more active than (RS)-camp...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.683
更新日期:1992-03-01 00:00:00
abstract::Synthesis of (1R,2S,5S,6R,8S)-3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid (2) from trans-4-hydroxy-L-proline (5) was attempted. A Diels-Alder reaction of 3,4-dehydroproline derivative 9 and cyclopentadiene afforded a single stereoisomer 11. The Diels-Alder adduct was smoothly converted to the hydrochloride of 2...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.1015
更新日期:2003-08-01 00:00:00
abstract::Several benzimidazole derivatives having electron-withdrawing or -donating substituent(s) at the benzene moiety were used as models of the imidazole moiety of purine bases and their nitration with nitrogen dioxide and ozone (so-called Kyodai nitration) were examined. Products were extracted from the reaction mixture w...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.570
更新日期:2004-05-01 00:00:00
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
更新日期:1992-11-01 00:00:00
abstract::When 8-bromoadenosine was incubated with cysteine at pH 7.2 and 37°C, an exclusive product was generated. This product was identified as a cysteine substitution derivative of adenosine at the 8 position, 8-S-L-cysteinyladenosine. The reaction accelerated as pH increased from mildly acidic to basic conditions. The isol...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c17-00731
更新日期:2018-01-01 00:00:00
abstract::Clotrimazole (CT)-containing proliposomes were prepared by penetrating an ethanol solution of CT and Egg phosphatidylcholine (PC) into microporous sorbitol particles, followed by vacuum evaporation of the solvent. As a result, CT proliposomes with free-flowing flowability were obtained. On contact with water, the prol...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.620
更新日期:2005-06-01 00:00:00
abstract::(+)-4(5)-[(2R,5R)-5-aminomethyltetrahydrofuran-2-yl]imidazole [(+)-1, imifuramine] and its 2R,5S-stereoisomer (+)-2 were expected as base compounds to develop selective human histamine H4-receptor ligands. The improved synthesis of (+)-1 was done via cyclization of a diazafulvene intermediate generated by Bu3P/N,N,N',...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.832
更新日期:2003-07-01 00:00:00
abstract::We describe the synthesis and biological evaluation of N-aryl-5-aryloxazol-2-amine derivatives that are able to inhibit 5-lipoxygenase (5-LOX), a key enzyme of leukotriene synthesis, for the treatment of inflammation-related diseases including asthma and rheumatoid arthritis. A novel structural moiety containing oxazo...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00033
更新日期:2015-01-01 00:00:00
abstract::The purpose of this study was to predict the stability of imipenem in a mixed infusion. The hydrolysis of imipenem in aqueous solution was found to be accelerated by pH, and by increasing concentrations of sodium bisulfite (SBS) and L-cysteine. Equations were derived for the degradation rate constants (k(obs)) of pH, ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c12-00427
更新日期:2013-01-01 00:00:00