Abstract:
:Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-Baylis-Hillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene reactions, and their utilization for the syntheses of the phoslactomycin family of antibiotics, glutamate receptor agonists and antagonists, and alkaloids with characteristic highly substituted pyrrolidinone core structures.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Hatakeyama Sdoi
10.1248/cpb.c14-00474subject
Has Abstractpub_date
2014-01-01 00:00:00pages
1045-61issue
11eissn
0009-2363issn
1347-5223pii
DN/JST.JSTAGE/cpb/c14-00474journal_volume
62pub_type
杂志文章,评审abstract::Stereoselective synthesis of the 16-membered diolide 27, a fully functionalized congener of lepranthin (1), is described. The requisite five asymmetric carbon centers in monomer 23 were constructed in a highly stereoselective manner by using different epoxide-opening reactions of α,β-unsaturated γ,δ-epoxy esters and e...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.525
更新日期:2011-01-01 00:00:00
abstract::A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp(2))-O bond formation reaction (SNAr) in the presence of anhydrous K(2)CO(3), followed by C(sp(2))-C(sp(2)) bond formation reaction (intramolecular palladium-catalyzed aryl-aryl coupling reaction) between aryl halides a...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1496
更新日期:2008-10-01 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::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
更新日期:1991-12-01 00:00:00
abstract::Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)-dien-12,6 alpha-olide (2), along with two previously reported sesquiterpenoids: 8 alpha-a...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1168
更新日期:2008-08-01 00:00:00
abstract::The reaction of lauroyl isothiocyanate and 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile was used to synthesize the title compound 2. Compound 2 could serve as the main building block in the synthesis of many target heterocyclic systems. Various fused pyrimidines were synthesized in the reactions of compo...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00047
更新日期:2015-01-01 00:00:00
abstract::When phenylalanine was irradiated at ultraviolet (UV) light, p-tyrosine, m-tyrosine and o-tyrosine were identified as hydroxylated products. From p-tyrosine and m-tyrosine, the formation of L-3,4-dihydroxyphenylalanine (DOPA) was observed. The hydroxylation of phenylalanine was prevented by radical scavengers, e.g., c...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.1417
更新日期:1990-05-01 00:00:00
abstract::A series of 43 stilbene derivatives that showed cytotoxicity against human lung carcinoma (A549) was analyzed using comparative molecular field analysis (CoMFA) for defining the hypothetic pharmacophore model. The polyoxylated stilbenes were found to be active inhibitors of tubulin polymerization. Several cis-stilbene...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.516
更新日期:2003-05-01 00:00:00
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
更新日期:1991-01-01 00:00:00
abstract::Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.781
更新日期:2008-06-01 00:00:00
abstract::Treatment of calf thymus deoxyribonucleic acid (DNA) with the horseradish peroxidase-H2O2 system resulted in efficient formation of 8-hydroxydeoxyguanosine (8-OH-dG) residues. It was concluded that singlet oxygen was the reactive species involved, based on experiments using active oxygen scavengers and D2O. For 8-OH-d...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.3072
更新日期:1990-11-01 00:00:00
abstract::ZnAB has the combined structure of N,N-bis(2-pyridylmethyl)ethylenediamine as a specific chelater for Zn(2+) and 1,3,5,7-tetramethyl-8-phenyl-boron dipyrromethene as a fluorophore. Complexation of ZnAB with Zn(2+) produces a remarkable enhancement of fluorescence intensity. ZnAB has the advantages of less sensitivity ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.700
更新日期:2004-06-01 00:00:00
abstract::In order to synthesize four stereoisomers of cystathionine (CYT), D- and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.1081
更新日期:2002-08-01 00:00:00
abstract::We designed a single unit type tablet formulation containing nateglinide to decrease both postprandial blood glucose level (PBG) and fasting blood glucose level (FBG) in normal beagle dogs. The tablet was a dry coated tablet comprising both a core tablet (an erosion matrix tablet: a controlled release portion(nateglin...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.57.907
更新日期:2009-09-01 00:00:00
abstract::A series of phthalazine and 1,2,3-benzotriazine derivatives which have heterocyclylpiperidino groups was synthesized and tested for cardiotonic activity in anesthetized dogs. Several 6,7-dimethoxyphthalazine derivatives showed relatively potent cardiotonic activity comparable to that of amrinone. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.2179
更新日期:1990-08-01 00:00:00
abstract::The intercalation reaction of diclofenac sodium (DFS) with layered inorganic compounds, gamma-titanium phosphate (gamma-TiP), proton type titanium oxide (H-TiO2) and sodium type synthetic mica (Na-TSM), was examined on. The direct reaction of DFS in ethanol-water mixed solvent resulted in the large amount accommodatio...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.1396
更新日期:2005-11-01 00:00:00
abstract::Tumor necrosis factor (TNF), a cytokine produced in macrophages, also acts as an endogenous pyrogen (EP). To investigate whether TNF has a role in the fever induced by Nocardia rubra cell wall skeleton (N-CWS), the relationship between fever and TNF production was studied in guinea pigs. N-CWS injected i.v. to guinea ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.2795
更新日期:1989-10-01 00:00:00
abstract::Four new cembrane diterpenes (1-4) and fifteen known cembranoids (5-19) were isolated from an Okinawan soft coral Lobophytum crassum. The structures of these four new cembranoids were determined on the basis of spectroscopic evidence. In particular, the absolute stereochemistry of 1, 2, 5 and 6 were elucidated by the ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.1203
更新日期:2010-09-01 00:00:00
abstract::The purpose of the present study was to quantify the degree of suppression of the bitterness of two amino acids (L-isoleucine (L-Ile), and L-phenylalanine (L-Phe)) which could be achieved by the addition of various test chemicals, and to examine the mechanism of this bitterness suppression. The test chemicals used wer...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.172
更新日期:2004-02-01 00:00:00
abstract::The production of sesquiterpene-type phytoalexins with a vetispyradiene skeleton by Hyoscyamus albus hairy roots induced by methyl jasmonate (MeJA) was reported in a previous paper. The production pattern on co-treatment with cupper sulfate and MeJA (CuSO(4)-MeJA) showed a TLC profile differing from that on treatment ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.934
更新日期:2010-07-01 00:00:00
abstract::Three new hydronaphthalenone derivatives (1-3) and one new dihydroramulosin derivative (4), were isolated from the endophytic fungus PSU-N24 together with eight known compounds. Their structures were elucidated by spectroscopic methods. Griseofulvin (9) displayed strong antifungal activity against Microsporum gypseum ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1687
更新日期:2008-12-01 00:00:00
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 agains...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.41.1846
更新日期:1993-10-01 00:00:00
abstract::Enantioselective fluorinating agents, (R)- and (S)-,N-fluoro-3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides (BNBT-F, 2) are readily prepared in 3 steps from racemic 3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides (5) via optical resolution and fluorination. These agents m...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.48.1954
更新日期:2000-12-01 00:00:00
abstract::1,3-Dicapryloyl-2-linoleoylglycerol (1), a novel triglyceride, was isolated from berries of Hippophae rhamnoides. The structure was elucidated on the basis of MS, 1D and 2D NMR experiments including HMQC and HMBC. The metal chelating, free radical scavenging, and lipid peroxidation inhibiting properties of the compoun...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.1021
更新日期:2005-08-01 00:00:00
abstract::Six new furostanol saponins called trigoneosides Ia, Ib, IIa, IIb, IIIa, and IIIb were isolated from a medicinal foodstuff, fenugreek seed, the seed of Trigonella foenum-graecum L. (Leguminosae) originating from India, together with two known saponins, glycoside D and trigofoenoside A. The structures of trigoneosides ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.81
更新日期:1997-01-01 00:00:00
abstract::In the present study, a novel series of 2-(2-(3-aryl-5-substituted-1,3,4-thiadiazol-2(3H)-ylidene)hydrazinyl)-4,4-diphenyl-1H-imidazol-5(4H)-one derivatives were designed and prepared via the reaction of the most versatile, hitherto unreported 2-(5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydrazinecarbot...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c16-00344
更新日期:2016-01-01 00:00:00
abstract::Orally disintegrating tablets (ODTs), which are administered without water, are beneficial for elderly patients and patients with dysphagia. Masking the unpleasant taste of a drug is an important factor associated with adherence of patients consuming ODTs. We prepared cocoa powder-containing ODTs of bitter-tasting reb...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c18-00629
更新日期:2019-01-01 00:00:00
abstract::A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human ca...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c13-00340
更新日期:2013-01-01 00:00:00
abstract::A one-pot conversion of allyl alcohols into selenochroman derivatives was achieved by treatment with a phenyl trimethylsilyl selenide (TMSSePh)-AIBr3 reagent system. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.1223
更新日期:2001-09-01 00:00:00
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
更新日期:1989-06-01 00:00:00