Abstract:
:The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initially formed one. Two diastereomeric Wieland-Miescher type compounds, having the allyl group at the angular position, were synthesized as optically pure forms.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Hiroya K,Takahashi T,Shimomae K,Sakamoto Tdoi
10.1248/cpb.53.207subject
Has Abstractpub_date
2005-02-01 00:00:00pages
207-13issue
2eissn
0009-2363issn
1347-5223pii
JST.JSTAGE/cpb/53.207journal_volume
53pub_type
杂志文章abstract::Manidipine dihydrochloride or benidipine hydrochloride will change to hydrate form in part, when differential scanning calorimetric (DSC) measurement is carried out together with lactose monohydrate. This interaction was accelerated by compressing their mixture. It can be suggested that the interaction may cause by th...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.503
更新日期:2005-05-01 00:00:00
abstract::Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.57.632
更新日期:2009-06-01 00:00:00
abstract::Two new phenolic amides, pharnilatins A (1) and B (2), were isolated from the seeds of Pharbitis nil. These new compounds possess a p-coumaroyl unit with a structurally unique side chain, (2S,3S)-2,3-dihydroxyputrescine. The chemical structures and absolute stereochemistries of the new compounds were determined on the...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.1532
更新日期:2010-11-01 00:00:00
abstract::The structures of the ternary palladium(II) complexes of the formulations [Pd(Gly)(bpy)](+)Cl(-).4H(2)O (Gly=glycine; bpy=2,2'-bipyridine) (1), [Pd(Gly)(phen)](+)Cl(-).4H(2)O (2) (phen=1,10-phenanthroline) and {[Pd(Gly)(bpa)](+)Cl(-)}(2).6H(2)O (3) (bpa=2,2'-bipyridylamine) were determined. All complexes are positivel...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.908
更新日期:2008-07-01 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::Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxy...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c16-00122
更新日期:2016-01-01 00:00:00
abstract::Two new lignans, 4-methoxymagnaldehyde B (1) and coumanolignan (2), were isolated from the stem bark of Magnolia obovata, together with 11 known compounds (3-13). The structures of compounds 1 and 2 were determined to be 5'-allyl-2'-hydroxyphenyl-4-methoxy-3-cinnamic aldehyde (1) and 6-allyl-8-(5'-allyl-2'-hydroxyphen...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.115
更新日期:2008-01-01 00:00:00
abstract::Cyclodextrins (CDs) are water-soluble host compounds having nano-size hydrophobic cavities that enable them to incorporate organic molecules in water. Optically inert CDs can be efficiently combined with various types of chromoionophores and fluoroionophores. In this study, using diverse combinations of phenylboronic ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.c16-00963
更新日期:2017-01-01 00:00:00
abstract::Two new iridoid glycosides, 7 beta,8 beta-epoxy-8 alpha-dihydrogeniposide (1) and 8-epiapodantheroside (2), were isolated, together with six known (3-8) and three artifact (9-11) iridoids, from the leaves of Gardenia jasminoides cv. fortuneana Hara. Their structures were established based on chemical and spectral data...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.1417
更新日期:2003-12-01 00:00:00
abstract::Four new compounds 1-4 were obtained from an oxidative coupling reaction of (E)-isorhapontigenin using FeCl(3) as oxidant. Their structures and stereochemistry were determined on the basis of spectroscopic evidence [UV, IR, MS, (1)H-, (13)C-NMR, NOE and 2D NMR], and their possible formation mechanisms were also discus...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.238
更新日期:2004-02-01 00:00:00
abstract::In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modificati...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.44.2300
更新日期:1996-12-01 00:00:00
abstract::A method for the preparation of insulin derivatives having protected sulfhydryl group(s) on definite site(s) on the molecule which uses anion-exchange high performance liquid chromatography on a TSKgel DEAE-2SW column for separation is described. Porcine insulin reacts with N-succinimidyl S-acetylthioacetate to afford...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.957
更新日期:1992-04-01 00:00:00
abstract::A new neolignan, (7R,8R)-5-O-demethylbilagrewin (1), together with four known lignans (2-5), were isolated from the heartwood of Santalum album (Santalaceae). The structure of 1 was determined by analysis of extensive spectroscopic data. The isolated compounds and derivatives were evaluated for their cytotoxic activit...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.587
更新日期:2010-04-01 00:00:00
abstract::Four new dibenzocyclooctadiene lignan glucosides, schisandrosides A-D (1-4), as well as two known rare nortriterpenoids, micrandilactone C (5) and propindilactone Q (6), were isolated from the roots of Schisandra chinensis BAILLON (Schisandraceae). The structure of compounds 1-4 were elucidated by physical and spectro...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00400
更新日期:2015-01-01 00:00:00
abstract::Thermodynamic studies were carried out to evaluate the binding of theophylline on adenosine deaminase (ADA) in 50 mM sodium phosphate buffer pH 7.5, at 300 K, using isothermal titration calorimetry (ITC). A simple method for determination of binding isotherm in the drug--ADA interaction was applied using ITC data. ADA...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.1179
更新日期:2004-10-01 00:00:00
abstract::Further studies by means of preparative HPLC led to the isolation of two new furostanol saponins, macrostemonoside J (1) and L (3), along with an artifact, macrostemonoside K (2) from the bulbs of Allium macrostemon. On the basis of chemical evidence and spectral analysis (1H-, 13C-NMR and FAB-MS), the structure of 1 ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.2180
更新日期:1994-10-01 00:00:00
abstract::A new monomethylated ganglioside, DSG-A (3), was obtained, together with four known gangliosides, compounds (1, 2, 4, 5), from the lipid fraction of the chloroform/methanol extract of the ovary of the sea urchin Diadema setosum. The structures of the new ganglioside was determined on the basis of chemical and spectros...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.734
更新日期:2008-05-01 00:00:00
abstract::Conjugates of 2-aminooxyethyliminodiacetic acid with estrone, testosterone, epiandrosterone, 17-alpha-hydroxy-progesterone and progesterone were synthesized and their complexes with Tc-99m were successfully prepared in good yields, which indicated the agent to be promising for metal-labeling of biomolecules and relate...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.47.413
更新日期:1999-03-01 00:00:00
abstract::The object of this study was to develop hydroxypropyl methylcellulose (HPMC) based cephalexin extended release tablet, which can release the drug for six hours in predetermined rate. Twenty-one batches of cephalexin tablets were prepared by changing various physical and chemical parameters, in order to get required th...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.978
更新日期:2003-08-01 00:00:00
abstract::Three novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.807
更新日期:2004-07-01 00:00:00
abstract::The synthesis and biological evaluation of [2-Valine-A] insulin ([Val2-A]insulin) is reported. In this insulin, the isoleucine residue in position A2, invariant in the majority of mammalian insulins, is substituted by valine. The same substitution, along with four others, occurs naturally in the insulin produced by th...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.670
更新日期:1989-03-01 00:00:00
abstract::Eight dermorphin (DM) analogs extended at the C-terminus, based on the sequence of prepro-DM deduced from the cDNA, were synthesized by a simultaneous solid-phase method in which a pair of peptides was synthesized in a single vessel. Six peptides (three pairs) were obtained in satisfactory yields (17-37%). In the opio...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.888
更新日期:1994-04-01 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::The synthesis and structure-activity relationships of a series of new azabicycloalkanes as 5-HT3 (serotonin-3) receptor antagonists are described. Our study on the azabicycloalkaneacetamide derivatives showed that 2,3-dihydroindole as the aromatic ring moiety afforded potent 5-HT3 receptor antagonist activity, as judg...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.43.1351
更新日期:1995-08-01 00:00:00
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
更新日期:2014-01-01 00:00:00
abstract::Three new anthraquinone glycosides, lasianthuoside A (1), B (2), and C (3), were isolated from the root of Lasianthus acuminatissimus MERR., The structural elucidation of these anthraquinones was mainly established on the basis of 1D and 2D NMR and HR-MS spectroscopic analysis. Ten known compounds, damnacanthol (4), d...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.54.297
更新日期:2006-03-01 00:00:00
abstract::A practical protocol to obtain accurate heat capacity values of pharmaceutical compounds using modulated-temperature differential scanning calorimetry was established. Three pharmaceutical compounds, acetaminophen, indomethacin, and tri-O-methyl-β-cyclodextrin were used as model compounds. Powder samples did not produ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c12-00928
更新日期:2013-01-01 00:00:00
abstract::Five compounds have been isolated from the dried whole plants of Selaginella uncinata, two of them were new chromone glycosides, 5-hydroxy-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside (uncinoside A) and 5-acetoxyl-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside (uncinoside B). Their structures were elucidated...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.1264
更新日期:2003-11-01 00:00:00
abstract::The purpose of this study was to develop and test a novel and simple method for evaluating the disintegration time of rapidly disintegrating tablets (RDTs) in vitro, since the conventional disintegration test described in the pharmacopoeia produces poor results due to the difference of its environmental conditions fro...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c13-00441
更新日期:2013-01-01 00:00:00
abstract::The conjugation of Ulex europaeus agglutinin I (UEAI) onto surface of liposomes has been demonstrated to effectively improve the intestinal absorption of antigen, subsequently induced strong mucosal and systemic immune responses. In this context, we prepared bovine serum albumin (BSA)-encapsulating UEAI-modified lipos...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.618
更新日期:2011-01-01 00:00:00