All issues
Volume 42, Issue 1
Displaying 1-35 of 35 articles from this issue
- |<
- <
- 1
- >
- >|
-
Akihiro NOGUCHI, Shin-ichi KONDO, Masayuki KUZUYA1994 Volume 42 Issue 1 Pages 1-4
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photoreaction of peroxy radicals of polytetrafluoroethylene (PTEE) was investigated by means of the molecular orbital (intermediate neglect of differential overlap/spectroscopy-configuration interaction (INDO/S-CI)) calculations of the excited states of model compounds for two types of radicals, i.e. the endchain peroxy and midchain peroxy radicals. Calculations showed that the midchain redicals are exited to the second lowest excited doublet (D2) state, which is responsible for the photoreaction, with much higher efficiency than the endchain peroxy radicals. The bond order perturbations accompanied by the transition from the ground doublet (D0) state to the D2 state in the midchain radicals seem to well explain the experimental results.View full abstractDownload PDF (586K) -
Ken-ichi IZUTSU, Sumie YOSHIOKA, Tadao TERAO1994 Volume 42 Issue 1 Pages 5-8
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stabilizing effect of mannitol during the freeze-drying of proteins was studied using L-lactate dehydrogenase (LDH, rabbit muscle), β-galactosidase (Escherichia coli) and L-asparaginase (Erwinia chrysanthemi) as model proteins. Crystallization of mannitol was studied by powder X-ray diffraction and differential scanning calorimetry (DSC), in relation to the stabilizing effect. All the enzymes were protected concentration-dependently by amorphous mannitol, but the stabilizing effect was decreased with an increase in mannitol crystallinity. The heat-treatment of frozen solutions above crystallization temperature prior to drying enhanced mannitol crystallization and LDH inactivation. The importance of maintaining excipients in an amorphous state during freeze-drying, previously reported for Aspergillus oryzae β-galactosidase (K. Izutsu et al., Pharm. Res., 10, 1233 (1993)), was confirmed using three different enzymes.View full abstractDownload PDF (654K) -
Kenji MATSUKI, Hirozumi INOUE, Akihiko ISHIDA, Mikio TAKEDA, Masako NA ...1994 Volume 42 Issue 1 Pages 9-18
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChiral bicyclic lactones (3, 8, 9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1, 2-dicarboxylic anhydrides (1, 4) and meso-cyclic-1, 2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1, 1'-bi-2-naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.View full abstractDownload PDF (1468K) -
Motomasa KOBAYASHI, Kazuyoshi KAWAZOE, Takumi OKAMOTO, Takuma SASAKI, ...1994 Volume 42 Issue 1 Pages 19-26
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcidic treatment of swinholide A (1), which was characterized as the major cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoei, provided several isomeric macrolides having different size of the dilactone ring structure. From the structure-activity correlation viewpoint, the in vitro cytotoxicities and in vivo antitumor activities of these dimeric macrolides, together with two monomeric macrolides which were synthesized from 1, have been examined.View full abstractDownload PDF (983K) -
Takashi MICHIDA, Hiroteru SAYO1994 Volume 42 Issue 1 Pages 27-30
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 4-Dinitrobenzenesulfenylnitrene (A) was produced by the oxidation of 2, 4-dinitrobenzenesulfenamide (1) with N-bromosuccinimide, and trapped as N-sulfenylaziridines (3-7). In the presence of a large excess of olefins, the aziridines were produced in 6-57% yields. On the other, when a large excess of 1 was used, the aziridines were synthesized in 62-72% yields based on the olefins. cis-Stilbene gave a mixture of cis-1-(2, 4-dinitrobenzenesulfenyl)-2, 3-diphenylaziridine (8) and the trans isomer (4). On the other hand, trans-stilbene gave only 4. These results suggest the involvement of a biradical intermediate in these reactions.View full abstractDownload PDF (594K) -
Takushi KURIHARA, Yasuhiko SAKAMOTO, Masato TAKAI, Kiyoko TSUKAMOTO, T ...1994 Volume 42 Issue 1 Pages 31-38
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS9-Methyl-12-carbaeudistomin (1, 13b-cis-1-amino-13-methyl-1, 2, 3, 4, 7, 8, 13, 13b-octahydro[1', 2']oxazepino-[2', 3', : 1, 2]pyrido[3, 4-b]indole) (2), which has a carbon atom instead of the sulfur atom in the D-ring of tetracyclic eudistomins (1), its 1, 10-trans isomer (3), and their 11, 12-didehydro derivatives (4 and 5) were synthesized from 2-vinylazetopyridoindoles (8 and 17) via the [2, 3]-Meisenheimer rearrangement of the corresponding N-oxides, for structure-activity relationship study of edistomins (1). Similarly, 5-amino-3, 6-epoxyhexahydroazocino[5, 4-b]-indoles (6 and 7) were synthesized from 2-ethylazetopyridoindole (33) via the [1, 2]-Meisenheimer rearrangement of the corresponding N-oxide.View full abstractDownload PDF (1193K) -
Hiroyuki AGETA, Kenji SHIOJIMA, Yoko ARAI, Hideki SUZUKI, Tamiko KIYOT ...1994 Volume 42 Issue 1 Pages 39-44
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 1H- and 13C-NMR signals of eleven triterpenoid hydrocarbons belonging to the hopene and migrated hopene groups were completely assigned by the application of modern NMR techniques, and the conformations are discussed on the basis of Chem3D Plus and MM2 calculations, and nuclear Overhauser effect spectroscopy spectra.View full abstractDownload PDF (929K) -
Kenji SHIOJIMA, Hiroyuki AGETA1994 Volume 42 Issue 1 Pages 45-47
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the leaves of Adiantum edgeworthii, two new triterpenoids, 19α-hydroxyadiantone (1) and fern-9(11)-en-25-oic acid (2) were isolated, together with fern-9(11)-ene (3), fern-7-ene (4), neohop-12-ene (5), filic-3-ene (6), hop-22(29)-ene (7), adiantone (8), hydroxyhopane (9) and zeorin (10). The structures of 1 and 2 were elucidated on the basis of spectral data and chemical correlations with a known compound.View full abstractDownload PDF (569K) -
Nobuko SAKURAI, Mamoru KOEDA, Takao INOUE, Masahiro NAGAI1994 Volume 42 Issue 1 Pages 48-51
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new triterpenol glycosides were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae) : 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside (1), C43H70O16, mp 222-223°C, [α]D +21.0° and 3-xylosyl-24-O-acetylhydroshengmanol 15-glucoside (2), C43H70O16, mp 208-210°C, [α]D+9.5°. On acidic hydrolysis, 1 afforded cimigenol (3) as an aglycone, and glucose and arabinose as sugars. On enzymatic hydrolysis with molsin, 1 afforded 24-O-acetylhydroshengmanol 15-O-glucoside (4). On the basis of chemical and spectral data, the structure of 1 was proposed to be (23R, 24S)-24-acetoxy-3-O-α-L-arabinopyranosyloxy-16, 23-epoxy-9, 19-cyclolanostane-15α, 16ξ, 25-triol 15-O-β-D-glucopyranoside.The other glycoside (2) showed, in its 13C-NMR spectrum, a pattern of chemical shifts very similar to that of 1. On acidic hydrolysis, 2 afforded cimigenol (3), xylose and glucose. On enzymatic hydrolysis with molsin, 2 afforded 4. From these results, the structure of 2 was proposed to be (23R, 24S)-24-acetoxy-3-O-β-D-xylo-pyranosyloxy-16, 23-epoxy-9, 19-cyclolanostane-15α, 16ξ, 25-triol 15-O-β-D-glucopyranoside.View full abstractDownload PDF (622K) -
Zenei TAIRA, Masao TAKEI, Koiti ENDO, Toshihiro HASHIMOTO, Yoko SAKIYA ...1994 Volume 42 Issue 1 Pages 52-56
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMarchantin A is a novel macrocyclic bis(bibenzyl)ether isolated from the liverwort Marchantia species. An X-ray study of its derivative, marchantin A trimethyl ether, revealed that the molecule possesses convex and concave surfaces, with a central hole on the concave surface. The centroid-centroid separations of opposing benzene rings are 8.80 and 4.55Å. A pharmacological study showed that the skeletal muscle relaxation activity is about 3.5 times less potent than that of d-tubocurarine. A comparison of the X-ray structure of marchantin A trimethyl ether and that of O, O', N-trimethyltubocurarine reported by Sobell et al. revealed that the molecules share almost the same macrocyclic bis(bibenzyl)ether skeleton structure, portions of which may therefore be crucial for the skeletal muscle relaxation activity.View full abstractDownload PDF (834K) -
Hiroshi OKADA, Tohru KOYANAGI, Nobutoshi YAMADA1994 Volume 42 Issue 1 Pages 57-61
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious benzoylphenylurea derivatives were synthesized as candidate prodrugs and their antitumor activities were examined in vivo against P388 leukemia. All of the prodrugs were soluble in most organic solvents and showed good antitumor activities against P388 leukemia cells in mice when dosed intraperitoneally or orally.View full abstractDownload PDF (687K) -
Kazuhiko KONDO, Masami TAKAHASHI, Hiroshi OHMIZU, Mamoru MATSUMOTO, Ik ...1994 Volume 42 Issue 1 Pages 62-66
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 2'-Disubstituted biphenyl compounds (1-15) were synthesized by using the Ullmann coupling reaction as a key step. The suppressive effect of these compounds against CCl4-induced liver injuries in mice was evaluated. An unsymmetrical biphenyl (14f) exhibited the most potent activity. The structure-activity relationship is discussed.View full abstractDownload PDF (797K) -
Masaru KIHARA, Minoru KASHIMOTO, Yoshimaro KOBAYASHI, Yoshimitsu NAGAO ...1994 Volume 42 Issue 1 Pages 67-73
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA variety of 1, 2, 3, 4-tetrahydroisoquinolin-4-ols (1-6) were prepared as part of our search for new norepinephrine (NE) potentiators and to clarify the structure-activity relationships. These compounds and some previously prepared compounds were compared with 2-methyl-4-phenyl-1, 2, 3, 4-tetrahydroisoquinolin-4-ol (PI-OH) (1a) for ability to potentiate NE. The potency, for 2-substitution, was found to be in the order : Me>Et>iso-Pr>H. The comopunds substituted by a halogen atom at the para position in the 4-phenyl group of PI-OH showed greater activities than did PI-OH, and the observed order of potency for the substitution was Cl>Br>F>H. The compound (4) methylated at the hydroxy group in PI-OH had greatly diminished activity. Although the desoxy compound (6) of PI-OH potentiated the response to NE at low concentrations, the potentiation was progressively masked by an inhibitory activity as the concentration of 6 was increased. In addition, the 4-cyclohexyl analogue (5) failed to potentiate NE. These results show the importance of the β-phenylethanolamine skeleton of PI-OH for producing NE potentiation without accompanying inhibitory action. The racemic 4-chlorophenyl analogue (2a) was resolved by HPLC to (R)-(+)-2a and (S)-(-)-2a. The NE-potentiating activity was found to reside exclusively in (R)-(+)-2a, which had the highest activity among compounds tested in this study; the activity ratio was 25 at 3×10-6M. The antidepressant activity of racemic 2a was evaluated by a forced swimming test. The activity of racemic 2a on the reduction of total duration of immobility in rats forced to swim was about 10 times that of desipramine. Thus, compound 2a appears to be a candidate for a new antidepressant.View full abstractDownload PDF (1105K) -
Kiyoshi TANIGUCHI, Kazunori TSUBAKI, Hiroaki MIZUNO, Kazuhiko TAKE, Ka ...1994 Volume 42 Issue 1 Pages 74-84
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of improving of the efficacy and decreasing the side effects of oxybutynin (1), N-[(tetrahydro-3- or 4-pyridyl)methyl]-, N-(4-piperidyl)-, and N-(3- or 4-piperidylalkyl)-2-hydroxyacetamides (3a-n, 4a-g) and the related carboxamides (3o-r, 4h-k, 13', 17) were synthesized and evaluated for inhibitory activity against urinary bladder rhythmic contraction in rats and for mydriatic activity in rats. Some of these compounds were superior to oxybutynin in both inhibitory activity against bladder contraction and selectivity between inhibitory activity against bladder contraction and mydriatic activity. Among them, N-[(1, 2, 3, 6-tetrahydro-4-pyridyl)methyl]- and N-[(1, 2, 3, 6-tetrahydro-1-methyl-4-pyridyl)methyl]-2-hydroxy-2, 2-diphenylacetamide (3e, 3f) exhibited the most potent inhibitory acitivity against bladder contraction (ED30=0.005 and 0.003 mg/kg i.v., respectively). Judging from the effect of 3e on detrusor contraction in vitro in guinea-pigs, it appeared that the inhibitory activity of 3e against bladder contraction in vivo was related mainly to its inhibitory activity against detrusor contraction in vitro induced with carbacol (antimuscarine-like activity). The selectivity (20-fold) of 3e between inhibitory activity against bladder contraction and mydriatic activity was greatly superior to that (0.48-fold) of oxybutynin.Compound 3e was synthesized by debenzylation (method E or F) of the corresponding N-[[1-(4-methoxybenzyl)-tetrahydro-4-pyridyl]methyl] derivative (3k), which was prepared by acylation (method B) of the corresponding (tetrahydro-4-pyridyl)methylamine (7k) or by reduction (method D) of the corresponding pyridinium chloride (14k) with NaBH4.View full abstractDownload PDF (1428K) -
Akihiro TASAKA, Katsunori TERANISHI, Yoshihiro MATSUSHITA, Norikazu TA ...1994 Volume 42 Issue 1 Pages 85-94
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn an effort to find potent antifungal agents, optically active sulfur-containing triazole derivatives, sulfides (3) and sulfonamides (4), were prepared and evaluated for antifungal activity against Candida albicans in vitro and in vivo. The sulfides (3) were prepared by the reaction of (2R, 3R)-2-(2, 4-difluorophenyl)-3-mercapto-1-(1H, 1, 2, 4-triazol-1-yl)-2-butanol (1) with various heteroarylmethyl chlorides in the presence of sodium methoxide. The sulfonamides (4) were synthesized starting from the disulfide (15) in three steps including oxidation of the corresponding sulfenamides (17). Some of the sulfur-containing triazole derivatives (3, 4) showed strong protective effects against candidosis in mice.View full abstractDownload PDF (1404K) -
Takanobu KUROITA, Mitsuyoshi YASUMOTO, Kenichi INABA, Masamitsu SAKAMO ...1994 Volume 42 Issue 1 Pages 95-100
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of N-(azabicyclo-3-yl)-2, 3-dihydrobenzofuran-7-carboxamide derivatives were synthesized and evaluated for serotonin-3 (5-HT3) receptor antagonistic activities assessed by 5-HT3 receptor binding (in vitro) and by the ability to antagonize the von Bezold-Jarisch reflex in rats (in vivo). In these compounds, 1-azabicyclo[2.2.2]oct-3-yl derivatives were more potent than 8-methyl-8-azabicyclo[3.2.1]oct-3-yl derivatives for 5-HT3 receptor antagonistic activities. The introduction of methyl groups at position 2 of the dihydrobenzofuran ring increased the pharmacological activities (dimethyl>monomethyl>dihydro). Furthermore, the stereoisomers of dimethyl-, monomethyl-, and dihydrobenzofuran derivatives were prepared to evaluate the stereoselectivity of their 5-HT3 receptor binding affinities. Concerning the basic part, the compounds bearing (S)-1-azabicyclo[2.2.2]octan-3-yl moiety were more potent than their counterparts. With respect to the methyl substituent at position 2 of the dihydrobenzofuran ring, the rank order of the potency was dimethyl≥(2S)-methyl>(2R)-methyl>dihydro. These rsults suggest that the (2S)-methyl group of the dihydrobenzofuran part contributes to the enhancement of the pharmacological activity. Among these compounds, (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)5-chloro-2, 3-dihydro-2, 2-dimethylbenzofuran-7-carboxamide hydrochloride (24) showed the highest affinity for 5-HT3 receptors (Ki=0.055 nM), and the most potent antagonisitic activity on the von Bezold-Jarisch reflex (ED50=0.18 μg/kg i.v.).View full abstractDownload PDF (897K) -
Hitoshi YOSHIMITU, Kazuhiro HAYASHI, Miki KUMABE, Toshihiro NOHARA1994 Volume 42 Issue 1 Pages 101-104
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new triterpene glycosides were isolated from the methanolic extract of Thalictri Herba (Takatogusa), the dried aerial parts of Thalictrum sp. plants (Ranunculaceae). They were designated as thalictosides III (1) and IV (2), being cycloartane-type glycosides, and thalictosides VI (3), VII (4) and VIII (5), being oleanene-type glycosides.By chemical and spectroscopic evidence, their structures were elucidated as 22R-21S, 23R-epoxy- and 22R-21R, 23R-epoxy-21-methoxycycloart-24-en-3β, 22, 30-triol 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranosides (1 and 2, respectively), 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-xylopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (3) and 3-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-xylopyranosyl oleanolic acid and hederagenin 28-O-β-D-glucopyranosyl esters (4 and 5, respectively).View full abstractDownload PDF (645K) -
Kazuya YAMASAKI, Masayuki KIKUOKA, Hiroyuki NISHI, Yoshio KOKUSENYA, T ...1994 Volume 42 Issue 1 Pages 105-107
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe determination of lecithin and choline in crude drugs was established by a combination of high performance liquid chromatography (HPLC) with electrochemical detector (ECD) and enzyme reaction. Lecithin in crude drugs extracted with a mixture of chloroform-methanol (2 : 1) at room temperature was hydrolyzed by phospholipase D. The hydrolyzate was injected to HPLC, and choline was separated from impurities by reverse phase column. The choline was converted to betaine and hydrogen peroxide by passing through column packed with immobilized choline oxidase. This hydrogen peroxide was detected by ECD. The peak area of hydrogen peroxide derived from lecithin was proportional to the concentration of lecithin from 0.10 to 1.52 μg/ml. Choline in crude drugs was extracted with ethanol under reflux and determined under the same HPLC conditions as lecithin. The peak area of hydrogen peroxide derived from choline was proportional to the concentration of choline from 0.01 to 0.45 μg/ml. The contents of lecithin and choline in 31 kinds of crude drugs were determined by these established methods. The results showed that Cervi Parvum Cornu, Kokurozin, Foenigraeci Semen and Psoraleae Semen contained more lecithin than other crude drugs, while Angelicae Radix, Foenigraeci Semen, Psoraleae Semen, and especially Hippocampus were found to contain more choline than other crude drugs.View full abstractDownload PDF (483K) -
Hisashi ISHII, Miki IMAI, Sumiko JOHJI, Shoji TAN, In-Sheng CHEN, Tsut ...1994 Volume 42 Issue 1 Pages 108-111
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA membrane filtration, the rejection effectivity of which mainly depends on the pore size of the membrane used, was applied to examination of the chemical constituents of Xanthoxylum nitidum (ROXB.) D. C. (Fagara nitida ROXB.), Rutaceae. The methanol extracts of the wood and bar were subjected to gradient filtrations. Each filtrate given by the separation was semi-quantitatively analyzed by HPLC. Magnoflorine (9), a phenolic quaternary aporphine alkaloid, was dramatically rejected by the ultrafiltration using a membrane with the pore size of 1000 in spite of its expected permeability through the membrane due to its smaller molecular weight than the pore size of the membrane used. Such clear rejection may be attributable to the phenolic functions in 9 because chelerythrine chloride (4), a quaternacy benzo[c]phenanthridine alkaloid, with a close molecular weight to that of 9, passed through the membrane.View full abstractDownload PDF (655K) -
Isao KOUNO, Chifumi IWAMOTO, Yuki KAMEDA, Takashi TANAKA, Chun-Shu YAN ...1994 Volume 42 Issue 1 Pages 112-114
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new triphenyl-type sesquineolignan, named simonsinol (1), was isolated from the bark of Illicium simonsii and its structure was elucidated based on the detailed analysis of its 1H- and 13C-NMR spectra. A new biphenylneolignan, named isomagnolone (5), was also isolated and its structure was determined by the analysis of the two dimensional (2D) NMR spectra.View full abstractDownload PDF (578K) -
Nguyen MINH DUC, Ryoji KASAI, Kazuhiro OHTANI, Aiko ITO, Nguyen THOI N ...1994 Volume 42 Issue 1 Pages 115-122
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFurther investigation on the saponin composition of rhizomes and roots of Panax vietnamensis HA et GRUSHV. has resulted in the isolation and structural elucidation of seven new dammarane saponins named vina-ginsenosides-R3 (12), -R4 (11), -R5 (16), -R6 (17), -R7 (6), -R8 (20), -R9 (22), together with the identification of six of known saponins including 20-gluco-ginsenoside-Rf (10), ginsenoside-Rc (4), notoginsenoside-R6 (9), quinquenoside-R1 (5), gypenoside XVII (2) and majoroside F1 (21). The structures of the novel saponins were established on the basis of chemical and spectral evidence. Vina-ginsenoside-R3 is the first naturally occurring glycoside of dammarenediol II, while vina-ginsenosides-R5 and -R6, two ocotillol-type saponins, are two other examples of saponins having the rare α-glucosyl linkage.View full abstractDownload PDF (1155K) -
Yasuko MORIMOTO, Mikio HOSOKAWA, Hiroteru SAYO, Yoshikazu TAKEUCHI1994 Volume 42 Issue 1 Pages 123-129
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of interaction between chloroprmazine (CPZ) and artificial lipid membranes, negatively or positively charged liposomes was studied by an electron spin resonance (ESR) technique. Analysis by a 5-doxyl stearic acid (DS) spin probe indicated that regardless of the electric charge of liposomes, CPZ disordered the hydrophobic region near the surface of lipid membranes at CPZ/lipid >1. In the same CPZ/lipid range, the lysis of liposomes was observed, and it was considered that the formation of the CPZ/lipid mixed micelles as a consequence of this collapse of liposomes would probably lead to the disordering of the 5-DS reporting region. As to the middle portion of the fatty acyl chains reported by the 12-DS spin probe, the membrane disordering action of CPZ was only detected with the negatively charged liposomes at a ratio of CPZ/lipid <1, but no membrane alteration was observed with the positively charged liposomes, regardless of the concentration range of CPZ used. In comparing these two opposite results, it is conceivable that the disordering at the 12-DS reporting region was probably induced by the cationized CPZ which would enter into the hydrocarbon-polar interface, leading to an expansion of the space between the hydrocarbon chains at this area. Also, a strong influence of CPZ on the innermost portion of the lipid bilayers was observed with both the negatively and positively charged liposomes, as reported by the 16-DS probe.This perturbing action presumably occured when undissociated CPZ molecules penetrated into the center of the bilayers (lipid core), which could have resulted in a reduction of hydrophobic interactions of the lipid molecules.View full abstractDownload PDF (1021K) -
Tomoko OTSUKA, Sumie YOSHIOKA, Yukio ASO, Tadao TERAO1994 Volume 42 Issue 1 Pages 130-132
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUtility of the microcalorimetric technique as a method of predicting drug stability was investigated. The hydrolysis of meclofenoxate hydrochloride and the oxidation of dl-α-tocopherol were chosen as model reactions. The hydrolysis rate was calculated from the time profile of the heat production. The rate was also calculated from the time profile of the degradation obtained by HPLC. The agreement in the rates confirms the applicability of microcalorimetry in determining rates of chemical reactions. The oxidation of dl-α-tocopherol was slow and a constant heat production rate was observed. The oxidation rate was calculated from the constant heat production rate and the enthalpy change for the reaction. To determine the rate constant required only a day by microcalorimetric method, whereas from the time profile of the degradation obtained by HPLC it would require almost one year. The saving in time to determine the degradation rate of dl-α-tocopherol demonstrates the value of this method.View full abstractDownload PDF (520K) -
Satoru WATANO, Akiko YAMAMOTO, Kei MIYANAMI1994 Volume 42 Issue 1 Pages 133-137
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of operational variables such as liquid flow rate, inlet air temperature and inlet air humidity on the properties of granules, prepared by a tumbling fluidized bed granulation while controlling the moisture content with an IR moisture sensor, were investigated experimentally. An increase in the liquid flow rate, i.e. the increase of the droplet size resulted in a slight increase of granule size and size distribution, while little influence was found of the inlet air temperature and humidity on granule size, size distribution or the apparent density. Remarkably good reproducibility was obtained in the granules prepared by the moisture control method. It was therefore concluded that by applying this method to the wet granulation by a type of fluidized bed, the effects of external circumstances could be fully eliminated and good reproducibility maintained.View full abstractDownload PDF (748K) -
Henry HEYMANN, Yasuhiro TEZUKA, Tohru KIKUCHI, Sutardjo SUPRIYATNA1994 Volume 42 Issue 1 Pages 138-146
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigation of the neutral fraction of the dried pods of Sindora sumatrana MIQ. has resulted in the isolation of three new sesquiterpenoids (2, 6 and 8) together with nine known ones (1, 3, 4, 5, 7, 9, 10, 11a and 12a), of which three (7, 10 and 12a) are reported for the first time from a natural source. One other compound, 4-stigmasten-3-one (13) (together with a sterol mixture; β-sitosterol, stigmasterol and campesterol) was also obtained. The structures of all the isolated sesquiterpenes were determined by means of spectroscopic methods, mainly two-dimensional NMR techniques, and the compounds were found to have the caryophyllane, humulane, clovane and caryolane skeletons. The NMR data of the isolated sesquiterpenes are also discussed.View full abstractDownload PDF (1271K) -
Yasuyuki KITA, Hiroshi MAEDA, Fumie TAKAHASHI, Seiji FUKUI, Toshihisa ...1994 Volume 42 Issue 1 Pages 147-150
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of the 2-cyanoethyl group for carboxyl-protection is described. This group was readily introduced by esterification using ethylene cyanohydrin and the deprotection was carried out under mild conditions using tetrabutylammonium fluoride in dimethylformamide-tetrahydrofuran.View full abstractDownload PDF (671K) -
Tozo FUJII, Tohru SAITO, Tomoko SUZUKI, Mayuri KUNUGI1994 Volume 42 Issue 1 Pages 151-153
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-Alkyl-1-methyladenines (12a, b) have been synthesized from 1-alkyl-4-aminomidazole-5-carboxamides (5a, b) in two steps [hence from adenine (1) in six steps]. The synthesis started with dehydration (using POCl3-HCONMe2) of 5a, b, readily obtainable from 1 in four steps according to previously reported procedures, and proceeded through cyclization between the resulting 4-(dimethylaminomethyleneamino)imidazole-5-carbonitrile derivatives (8a, b) and MeNH2. Similar cyclization between 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile (11c) and MeNH2 yielded 7-benzyl-1-methyladenine (12c).View full abstractDownload PDF (650K) -
Tomohiro INOUE, Tenji KONISHI, Shiu KIYOSAWA, Yasuhiro FUJIWARA1994 Volume 42 Issue 1 Pages 154-155
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new 2, 5-dihydrofuryl-γ-lactam derivatives, fulvanine D and E have been extracted from Hemerocallis fulva L. var. kwanso REGEL along with fulvanine A, B and C. The structures of fulvanine D and E have been established as 1-(3-hydroxymethyl-2, 5-dihydro-2-furyl)azacyclopenta-3-hydroxy-5-methoxy-2-one (1) and 1, 2, 4, 5, 5a, 6, 7, 8, -8a, 8b-decahydro-1, 5-dioxa-8a-aza-asym-indacen-7-hydroxy-8-one (2).View full abstractDownload PDF (397K) -
Makoto OTSUKA, Yoshihisa MATSUDA1994 Volume 42 Issue 1 Pages 156-159
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of humidity on mixtures of nitrofurantoin and crystalline lactose or microcrystalline cellulose was investigated by X-ray diffraction analysis, water content measurement and thermogravimetry. The water content of 50% (w/w) mixture was measured after storage at 95 and 100% relative humidity (RH), 40°C for 24h. The hydration of the mixture containing microcrystalline cellulose at 95% RH was the slowest, and that containing lactose at 100% RH was the fastest. The hydration process of nitrofurantoin anhydride was analyzed based on the three-dimensional phase boundary theory. The hydration rate of the nitrofurantoin was accelerated by adding lactose, but not by microcrystalline cellulose. Since lactose had a critical relative humidity at around 95% RH, the hydration of the mixture occurred in the solution after the lactose rapidly dissolved by deliquescence. However, the hydration rates of the mixture with microcrystalline cellulose were much slower than those of the anhydride.View full abstractDownload PDF (618K) -
Tsunemasa MIZUNO, Masahiro HANAMORI, Koichi AKIMOTO, Hiroshi NAKAGAWA, ...1994 Volume 42 Issue 1 Pages 160-162
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe wavelength dependency and the mechanism of photo-oxidation of ethyl 2-[4, 5-bis(4-methoxyphenyl)thiazole-2-yl]pyrrol-1-ylacetate (KBT-3022) in solution were investigated. The wavelength contributing to the photo-degradation of KBT-3022 in a mixture of acetonitrile-H2O (1 : 1) was found to be the near ultraviolet region, between 400 and 270 nm.The photo-oxidation of KBT-3022 was enhanced by the presence of rose bengal, which generates singlet oxygen as a photosensitizer, and by the presence of D2O in which the lifetime of singlet oxygen is about 10 times longer than in H2O. On the other hand, photo-oxidation was inhibited by the presence of sodium azide, or 1, 4-diazabicyclo[2.2.2]octane, both of which are known to be singlet oxygen quenchers. These results suggest that KBT-3022 acts by itself as a photosensitizer in its own photo-oxidation. Thus, the photo-degradation of N-methylpyrrole was enhanced by the presence of KBT-3022. It is concluded from these results that KBT-3022 reacts with singlet oxygen to form KBT-3022 endo-peroxide intermediate, and then undergoes hydrolysis to afford 5-hydroxylactam (D2).View full abstractDownload PDF (539K) -
Yoshiteru WATANABE, Yasushi KANZAKI, Makiko FUJII, Yoshiaki MATSUMOTO, ...1994 Volume 42 Issue 1 Pages 163-166
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction between a sodium-type synthetic mica (Na-TSM), a model material of reactive layered compounds, and phosphatidylcholine (PC) in a solid dispersion (IM-PC) with indomethacin (IM), a model drug, was investigated using X-ray diffraction analysis. It was found that IM-PC interacts with Na-TSM, and can be immobilized in the interlayer space by means of heating. When IM mole fractions in IM-PC increased from 0.25 to 0.5, the amount of IM intercalated into Na-TSM increased correspondingly from 5-18%. Consequently, it was determined that inorganic layered compounds, such as Na-TSM, intercalated with drugs in PC can be obtained.View full abstractDownload PDF (546K) -
Hirozumi INOUE, Susumu NAKAMURA, Hisao OTSUKA, Mitsunori GAINO, Tsuneh ...1994 Volume 42 Issue 1 Pages 167-172
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites of clentiazem in the urine or bile of rats and dogs were investgated. 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 procedures fundamentally similar to those empolyed in the synthesis of the corresponding metabolites of diltiazem.View full abstractDownload PDF (831K) -
TEMPERATURE CONTROL FOR THE DIASTEREOSELECTIVE HYDROLYSIS OF DIPEPTIDE ESTERS IN THE BUFFER SOLUTIONRyuichi UEOKA, Yoshito MATSUMOTO, Tetsuo ITO, Yoko MATSUMOTO, Yasuo KA ...1994 Volume 42 Issue 1 Pages 173-175
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA remarkably high stereoselectivity was attained for the hydrolysis of dipeptide p-nitrophenyl esters (DL/LL=101 for Z-Phe-Phe-PNP and DL/LL=71 for Z-Phe-Leu-PNP) without a catalyst in pH 9.5, 0.02 M carbonate buffer at the optimum temperature (32.5°C).View full abstractDownload PDF (440K) -
Ryohei KATO, Osamu TAKAHASHI, Yoshiaki KISO, Ikuo MORIGUCHI, Shuichi H ...1994 Volume 42 Issue 1 Pages 176-178
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructures of two enzyme-inhibitor complexes of human immunodeficiency virus-1 protease with allophenylnorstatine derivatives were obtained from molecular dynamics simulation in aqueous solution. The stronger inhibitor gave considerably smaller fluctuation at P3 site, which formed hydrogen bonding with the enzyme flap region.View full abstractDownload PDF (504K) -
Yukio MASAKI, Toshihiro IMAEDA, Makoto KAWAI1994 Volume 42 Issue 1 Pages 179-181
Published: January 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fungal metabolite, LL-P880β [6S-(1'S, 2'R-dihydroxypentyl)-4-methoxy-5, 6-dihydropyran-2-one] (1), was synthesized unambiguously from diethyl (R, R)-tartrate (3) as a chiral pool via highly stereoselective construction of the C7'-asymmetric carbon of the intermediate 6, 8-dioxabicyclo[3.2.1]octane derivative (8a), and the stereochemistry of the C6-chiral center of the metabolite was chemically confirmed as (S).View full abstractDownload PDF (410K)
- |<
- <
- 1
- >
- >|