Abstract:
:A series of 4-aza-5 alpha-androstane compounds with one or two aromatic moieties in the carbamoyl group at the C-17 position were synthesized and their inhibitory activities for rat and human prostatic testosterone 5 alpha-reductase were tested in vitro. Compounds with one aromatic moiety in the carbamoyl group showed high inhibitory activity for rat 5 alpha-reductase, but little for human prostatic 5 alpha-reductase. On the other hand, compounds with two aromatic moieties had potent inhibitory activities for both rat and human 5 alpha-reductase. The structural requirements for potent inhibition for both enzymes are discussed in relation to the spatial arrangement of the C-17 carbamoyl group.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Kurata H,Ishibashi K,Saito S,Hamada T,Horikoshi H,Furukawa Y,Kojima Kdoi
10.1248/cpb.44.115subject
Has Abstractpub_date
1996-01-01 00:00:00pages
115-21issue
1eissn
0009-2363issn
1347-5223journal_volume
44pub_type
杂志文章abstract::Enzymatic and post-translational modifications (PTMs) such as ubiquitination, acetylation, and methylation occur at lysine residues. The PTMs play critical roles in the regulation of the protein functions, and thus, various cellular processes. In addition, aberrations of the PTMs are associated with various diseases, ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.c19-00741
更新日期:2020-01-01 00:00:00
abstract::Doxazosin mesylate (DXM) sustained release pellets were prepared by an extrusion-spheronization and fluid-bed coating technique. The core pellets containing DXM were prepared by extrusion-spheronization technique, and coated by a fluid-bed coater to control the release of DXM. The factors affecting to properties of pe...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c12-00767
更新日期:2013-01-01 00:00:00
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 a...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.57.321
更新日期:2009-03-01 00:00:00
abstract::Improved synthesis of the trans-3,5-disubstituted pyrrolidin-3-ylthio side-chain of the novel carbapenem 1 was achieved via stereoselective reduction of the 1-aryl-1-butanone derivative 5 and successive intramolecular cyclization of the resulting chiral alcohol 6. The 1-aryl-1-butanone derivative 5 was obtained by a c...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.1500
更新日期:2001-11-01 00:00:00
abstract::Three new glycosides, 7-deoxyloganic acid beta-D-glucopyranosyl ester (1), (3R)-hydrangenol 8,4'-di-O-beta-D-glucopyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-beta-D-glucopyranoside (3), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO (Saxifragaceae). Th...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.610
更新日期:2008-04-01 00:00:00
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
更新日期:2000-03-01 00:00:00
abstract::Based on the result of X-ray crystallographic analysis of our peroxisome proliferator-activated receptor alpha and delta (PPARalpha/delta) co-agonist complexed with human PPAR ligand binding domain (LBD), we designed and synthesized an optically active fluorescent PPARalpha/delta co-agonist, which has a pyrene unit in...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1357
更新日期:2008-09-01 00:00:00
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
更新日期:2008-05-01 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::The structural conversion of the prion protein (PrP) from the normal cellular isoform (PrP(C)) to the posttranslationally modified form (PrP(Sc)) is thought to relate to Cu²⁺ binding to histidine (H) residues. Traditionally, the binding of metals to PrP has been investigated by monitoring the conformational conversion...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.965
更新日期:2011-01-01 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 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::Two novel triterpenoid saponins, ardisicrenoside C (1) [3 beta-O-(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)- [beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)-16 alpha, 28-dihydroxy-olean-12-en-30-oic acid 30-O-beta-D-glucopyranosyl ester] and ardisicrenoside D (2) [3 beta-O-(beta-D-xylopyr...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.2309
更新日期:1994-11-01 00:00:00
abstract::The metabolites of clentiazem in the urine or bile of rats and dogs were investigated. Fifteen basic, 6 acidic, 2 neutral and 4 conjugated metabolites were isolated. In the present paper, fourteen reference compounds as shown in Charts 1, 2 and 3 were synthesized to identify the structures of the metabolites in proced...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.167
更新日期:1994-01-01 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::alpha,alpha-Disubstituted amino acids are alpha-amino acids in which the hydrogen atom at the alpha-position of the L-alpha-amino acid is replaced with an alkyl substituent. The introduction of an alpha-alkyl substituent changes the properties of amino acids, with the conformational freedom of the side chain in the am...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.55.349
更新日期:2007-03-01 00:00:00
abstract::Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione c...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.1285
更新日期:2011-01-01 00:00:00
abstract::Five new compounds, hibicuslide A (1), hibicuslide B (2), hibicuslide C (3), hibicutaiwanin (4), hibicusin (5), and fifty-one known compounds have been isolated from the stems of Hibiscus taiwanensis. The structures of these compounds were determined by spectroscopic and chemical transformation methods. Among them, ma...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.56
更新日期:2005-01-01 00:00:00
abstract::5,15-Unsymmetrically disubstituted and beta-unsubstituted porphyrins such as 5-R, 15-(3,5-dimethoxyphenyl) porphyrins [where R=2-benzyloxy-1-naphthyl (1), 2-(2-naphthylmethoxy)-1-naphthyl (2), anthryl (3), or 2,4,6-triphenylphenyl (4)] and 5-(2-benzyloxy-1-naphthyl), 10,15,20-tri(3,5-dimethoxyphenyl) porphyrin (1') we...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1041
更新日期:2008-07-01 00:00:00
abstract::To investigate the possible mechanism of the stimulatory effect of a hot water extract from Artemisia leaf (Artemisia princeps PANPANINI) (AFE) on the proliferation of endothelial cells, cells from bovine aorta were cultured for 72 h in RPMI1640 medium supplemented with 10% fetal calf serum in the presence of 5 microg...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.2494
更新日期:1990-09-01 00:00:00
abstract::A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2-11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1-11 was examined on the basis of inhibitory activity aga...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.371
更新日期:2011-01-01 00:00:00
abstract::The analysis of genotoxic impurities (GTIs) in active pharmaceutical ingredients (APIs) is a challenging task. The target detection limit (DL) in an API is typically around 1 ppm (1 µg/g API). Therefore, a sensitive and selective analytical method is required for their analysis. 4-Chloro-1-butanol, an alkylating agent...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c13-00916
更新日期:2014-01-01 00:00:00
abstract::Gambir, the aqueous extract from Uncaria gambir (Rubiaceae), has been used as an astringent medicine in Asian countries. Investigation of the constituents in the extract led to the isolation of four chalcane-flavan dimers, gambiriin A1 (6), A2 (7), B1 (8), and B2 (9), in addition to (+)-catechin (1), (+)-epicatechin (...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.55.268
更新日期:2007-02-01 00:00:00
abstract::A new lanostane-type triterpene, 29-hydroxypolyporenic acid C (8), was isolated from the dried sclerotia of Poria cocos together with eight other known compounds pachymic acid (1), dehydropachymic acid (2), 3-acetyloxy-16alpha-hydroxytrametenolic acid (3), polyporenic acid C (4), 3-epi-dehydropachymic acid (5), 3-epi-...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1459
更新日期:2008-10-01 00:00:00
abstract::We have identified a novel cardiac steroid, 11,19-epoxy-19-methoxytelocinobufagin, named marinosin (1), in the skin of the toad, Bufo marinus (L.) Schneider. The treatment of compound 1 with 50% CH3CN containing 0.1% trifluoroacetic acid yielded a 11 alpha-hydroxyhellebrigenin (2), which has not previously been isolat...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.249
更新日期:1997-02-01 00:00:00
abstract::Biodegradable pasty-type copolyesters with a relatively low molecular weight of 4500 were synthesized by direct copolycondensation of epsilon-caprolactone (CL) and delta-valerolactone (VL) in the absence of catalysts to evaluate in vivo capabilities of the polymer for implantable controlled release devices in drug del...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.39.2096
更新日期:1991-08-01 00:00:00
abstract::Each testosterone [125I]iodinated histamine derivative where [125I]iodinated histamines were linked to respective 15 alpha- and 15 beta-carboxymethyltestosterone (15 alpha- and 15 beta-CMT), testosterone-3-(O-carboxymethyl)oxime (T-3-CMO) and testosterone-17 beta-hemisuccinate (T-17-HS) were tested for their usefulnes...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.951
更新日期:1990-04-01 00:00:00
abstract::Bioassay-directed fractionation of the extract of the cyanobacterium P. tenue led to the isolation of the three classes of glycolipids, viz., monogalactosyl diacylglycerol (MGDG), digalactosyl diacylglycerol (DGDG), and sulfoquinovosyl diacylglycerol (SQDG) as anti-tumor-promoters. In comparing the anti-tumor-promotin...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.41.1664
更新日期:1993-09-01 00:00:00
abstract::A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6-hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6-Alkyl-8-ergolinemethanols, prepared from...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.1463
更新日期:1994-07-01 00:00:00
abstract::This study examined the intestinal transport of five harman alkaloids using the Caco-2 cell monolayer as a model of the human intestinal mucosa. Transport parameters, permeability coefficients and percent transports, were calculated and compared under identical conditions with atenolol. Permeability coefficients were ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.394
更新日期:2004-04-01 00:00:00