Abstract:
:The synthesis of acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorter, and the total yield was 4.5% greater than the previous synthesis. Acetomycin analogs with benzoyloxy and pivaloyloxy groups, instead of an acetoxy group at the 5-position of the gamma-butyrolactone ring were designed as esterase-resistant models and prepared similarly. Although they showed a similar level of cytotoxicity as acetomycin in vitro, they were not resistant to porcine liver esterase, and lost cytotoxicity in vivo.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Uenishi J,Kobayashi N,Komine S,Okadai T,Yonemitsu O,Sasaki T,Yamada Ydoi
10.1248/cpb.47.517subject
Has Abstractpub_date
1999-04-01 00:00:00pages
517-23issue
4eissn
0009-2363issn
1347-5223journal_volume
47pub_type
杂志文章abstract::A full account is given of the first chemical synthesis of the antitumor antibiotic guanine 7-oxide (5) and its 9-substituted derivatives (24a--k and 26). Coupling of appropriate primary amines (17a--e, g--k) with phenacyl bromide (16) produced, after treatment with HCl, the corresponding N-substituted phenacylamine h...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.343
更新日期:1992-02-01 00:00:00
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
更新日期:1989-06-01 00:00:00
abstract::We have developed a catalytic aerobic oxidative dimerization reaction of benzofuranones using a Pd(II)-µ-hydroxo complex. Radical-radical cross-coupling of the resulting dimers with azo compounds enabled the one-pot synthesis of structurally congested benzofuranones having two distinct vicinal all-carbon quaternary ce...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c20-00359
更新日期:2020-01-01 00:00:00
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journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.47.732
更新日期:1999-06-01 00:00:00
abstract::From the ethyl acetate fraction of the stem bark of Camellia japonica, three new triterpenoids, 3beta-O-acetyl-16beta-hydroxy-12-oxoolean (6), 3beta-O-acetyl-16beta-hydroxy-11-oxoolean-12-ene (7), and 3beta-O-acetyl-16beta-hydroxyolean-12-ene (8), along with seven known compounds, 3alpha-hydroxy-1-oxofriedelan (1), fr...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.121
更新日期:2010-01-01 00:00:00
abstract::Peptides mimicking chemokine receptor CCR5 were synthesized and their anti-HIV-1 activities evaluated. Prepared compounds, especially a sulfated derivatives, showed significant anti-HIV-1 activities. Furthermore, a hybrid molecule linked to an N-carbomethoxycarbonyl-prolyl-phenylalanine (CPF) moiety had a greater effe...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.48.308
更新日期:2000-02-01 00:00:00
abstract::A series of N-azabicycloalkyl-1-alkyl-2-oxo-1,2-dihydro-3-quinolinecarboxamides were synthesized and tested for serotonin 5-HT4 receptor-stimulating effects in the regulation of electrically-evoked contraction in guinea pig muscle. Among them, N-azabicycloalkyl-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (8c,...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.48.2003
更新日期:2000-12-01 00:00:00
abstract::The influence of various phenolic compounds on the lactoperoxidase (LPO)/hydrogen peroxide (H2O2)-catalyzed oxidation of biochemical reductants such as reduced beta-nicotinamide adenine dinucleotide (NADH), reduced beta-nicotinamide adenine dinucleotide phosphate (NADPH) or reduced glutathione (GSH) was investigated b...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.299
更新日期:2001-03-01 00:00:00
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journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.2483
更新日期:1992-09-01 00:00:00
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
更新日期:2006-05-01 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::Four hypotensive peptides called elapherine-A, -B, -C and -D were isolated from the body of Elaphe climacophora after removal of the internal organs. Elapherine-A, which had the lowest molecular weight, exhibited a prolonged fall for 5 min in the blood pressure of spontaneously hypertensive rats, whereas elapherin-B, ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.1004
更新日期:1990-04-01 00:00:00
abstract::A novel series of quinoline azodyes (5-(4'-derivatives phenyldiazo)-8-hydroxy-7-quinolinecarboxaldehyde)) (HL1-HL5) has been prepared and characterized by elemental analyses, 1H-NMR and IR spectra. The IR spectral data indicate that the compounds can exist in two resonance structures. Proton-ligand dissociation consta...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.1308
更新日期:2001-10-01 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::Two major and two minor forms of dihydrodiol dehydrogenase with similar molecular weights of around 36000 were purified from monkey liver cytosol. All the forms oxidized trans-dihydrodiols of benzene and naphthalene and reduced aromatic aldehydes, but showed differences in charge, specificity for other substrates and ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.2852
更新日期:1989-10-01 00:00:00
abstract::Licorice is one of the ancient and most frequently applied herbs for its diverse phytochemicals. At present, wild resources of licorice have rapidly declined with increasing demand and the proportion of cultivated products in the market is quickly growing. However, the different level in chemical composition between t...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c19-00423
更新日期:2019-01-01 00:00:00
abstract::The interaction between FSM-16 and flurbiprofen (FBP) in the mesopores of FSM-16 was investigated by using three types of FSM-16 with different pore diameters, i.e., FSM-16(Oc), FSM-16(Do) and FSM-16(Doc) (pore diameters 16.0, 21.6, 45.0 A, respectively). Solid dispersions of 30% FBP-70% FSM-16 were prepared by solven...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.974
更新日期:2005-08-01 00:00:00
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journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.78
更新日期:2001-01-01 00:00:00
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
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更新日期:2008-08-01 00:00:00
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journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.2147
更新日期:1992-08-01 00:00:00
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
更新日期:2001-08-01 00:00:00
abstract::A novel in-die evaluation method of tablet capping tendency was proposed based on a force-displacement curve and stress relaxation parameter in a tableting process. In our previous study (Chem. Pharm. Bull., 59, 2011, Nakamura et al.), the phase diagram consisting of elastic recovery energy (E(e)) and plastic deformat...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.60.772
更新日期:2012-01-01 00:00:00
abstract::The hypothesis that oxidative stress contributes to renal dysfunction in sinoaortically denervated (SAD) rats was investigated. Rats were sinoaortically denervated and received treatment with tempol (0.5 mmol/L in drinking water) for 8 weeks. Although the tempol treatment of the SAD rats had no significant effect on b...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c16-00318
更新日期:2016-10-01 00:00:00
abstract::Chemical and pharmacological studies of Panax vietnamensis (Vietnamese ginseng; VG) have been reported since its discovery in 1973. However, the content of each saponin in different parts of VG has not been reported. In this study, 17 ginsenosides in the different underground parts of P. vietnamensis were analyzed by ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00369
更新日期:2015-01-01 00:00:00
abstract::A new series of 3-(5-3-methyl-5-[(3-methyl-7-5-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-1,3,4-thiadiazol-2-ylbenzo[b]furan-5-yl)methyl]benzo[b]furan-7-yl-1,3,4-thiadiazol-2-yl)-2-(aryl)-1,3-thiazolan-4-one 5a-j has been synthesized by the reaction of N2-[(E)-1-(4-methylphenyl)methylidene]-5-(3-methyl-5-[3-methyl-7-(5-[(E)-...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.805
更新日期:2010-06-01 00:00:00
abstract::Three new natural sesquiterpene coumarins, isofeterin (1), lehmannolol (3), sinkianone (4), and one known compound, lehmannolone (2), were isolated from the roots of Ferula teterrima and Ferula sinkiangensis. Their chemical structures were established on the basis of spectroscopic analysis, including X-ray crystallogr...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.54.1595
更新日期:2006-11-01 00:00:00
abstract::The effect of the modification of insulin (INS) with p-succinylamidophenyl (SA)-alpha-D-glucopyranoside (SAPG), SA-alpha-D-mannopyranoside and SA-alpha-L-arabinopyranoside on the enzymatic degradation and the hypoglycemic effect in rats was studied. When SAPG-INS was administered intraintestinally in the absence of bi...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.1983
更新日期:1990-07-01 00:00:00
abstract::The release properties of phenylpropanolamine hydrochloride (PPA) from ethylcellulose (EC) matrix granules prepared by an extrusion granulation method were examined. The release process could be divided into two parts; the first and second stages were analyzed by applying square-root time law and cube-root law equatio...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.298
更新日期:2004-03-01 00:00:00
abstract::A novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this series trans-N-4-[4-cy...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.402
更新日期:2005-04-01 00:00:00
abstract::Targeted protein degradation by small molecules is an emerging modality with significant potential for drug discovery. We previously developed chimeric molecules, termed specific and non-genetic inhibitor of apoptosis protein (IAP)-dependent protein erasers (SNIPERs), which induce the ubiquitylation and proteasomal de...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c18-00567
更新日期:2019-03-01 00:00:00