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野口 章公, 近藤 伸一, 葛谷 昌之
1994 年 42 巻 1 号 p.
1-4
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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 (D
2) 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 (D
0) state to the D
2 state in the midchain radicals seem to well explain the experimental results.
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伊豆津 健一, 吉岡 澄江, 寺尾 允男
1994 年 42 巻 1 号 p.
5-8
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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松木 健司, 井上 博純, 石田 昭彦, 武田 幹男, 中川 昌子, 日野 亨
1994 年 42 巻 1 号 p.
9-18
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Chiral 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 (LiAlH
4)-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 (Et
3SiH) and trifluoroacetic acid (CF
3CO
2H) 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.
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小林 資正, 川添 和義, 岡本 工, 佐々木 琢磨, 北川 勲
1994 年 42 巻 1 号 p.
19-26
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Acidic 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.
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道田 隆, 佐用 博照
1994 年 42 巻 1 号 p.
27-30
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
2, 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.
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栗原 拓史, 坂本 靖彦, 高井 雅人, 塚本 貴庸子, 酒井 朋子, 春沢 信哉, 米田 龍司
1994 年 42 巻 1 号 p.
31-38
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
9-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.
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上田 博之, 塩島 憲治, 荒井 洋子, 鈴木 秀樹, 清谷 多美子
1994 年 42 巻 1 号 p.
39-44
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The
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.
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塩島 憲治, 上田 博之
1994 年 42 巻 1 号 p.
45-47
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
From 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.
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桜井 信子, 小枝 守, 井上 隆夫, 永井 正博
1994 年 42 巻 1 号 p.
48-51
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Two new triterpenol glycosides were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae) : 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside (1), C
43H
70O
16, mp 222-223°C, [α]
D +21.0° and 3-xylosyl-24-O-acetylhydroshengmanol 15-glucoside (2), C
43H
70O
16, 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.
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平良 全栄, 武井 正夫, 遠藤 晃市, 橋本 敏弘, 崎谷 陽子, 浅川 義範
1994 年 42 巻 1 号 p.
52-56
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Marchantin 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.
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岡田 宏, 小柳 徹, 山田 修逸
1994 年 42 巻 1 号 p.
57-61
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Various 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.
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近藤 一彦, 高橋 政巳, 大水 博, 松本 守, 太口 育彦, 岩崎 為雄
1994 年 42 巻 1 号 p.
62-66
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
2, 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 CCl
4-induced liver injuries in mice was evaluated. An unsymmetrical biphenyl (14f) exhibited the most potent activity. The structure-activity relationship is discussed.
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木原 勝, 樫本 稔留, 小林 良磨, 長尾 善光, 守時 英喜
1994 年 42 巻 1 号 p.
67-73
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A 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.
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谷口 清, 椿 一典, 水野 裕章, 嶽 一彦, 奥村 和央, 寺井 孝雄, 塩川 洋一
1994 年 42 巻 1 号 p.
74-84
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
With 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 (ED
30=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 NaBH
4.
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田坂 昭弘, 寺西 克倫, 松下 義弘, 田村 典一, 林 良吾, 小此木 研二, 伊藤 克己
1994 年 42 巻 1 号 p.
85-94
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
In 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.
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黒板 孝信, 安本 光由, 稲葉 賢一, 酒盛 政光, 竹原 修造, 川北 武志
1994 年 42 巻 1 号 p.
95-100
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A series of N-(azabicyclo-3-yl)-2, 3-dihydrobenzofuran-7-carboxamide derivatives were synthesized and evaluated for serotonin-3 (5-HT
3) receptor antagonistic activities assessed by 5-HT
3 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-HT
3 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-HT
3 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-HT
3 receptors (K
i=0.055 nM), and the most potent antagonisitic activity on the von Bezold-Jarisch reflex (ED
50=0.18 μg/kg i.v.).
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吉満 斉, 林 和弘, 隈部 美希, 野原 稔弘
1994 年 42 巻 1 号 p.
101-104
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Five 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).
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山崎 一矢, 菊岡 正之, 西 博行, 国仙谷 良男, 宮本 尚明, 松尾 賢明, 佐藤 忠司
1994 年 42 巻 1 号 p.
105-107
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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石井 永, 今井 未来, 上治 純子, 丹 昭治, 陳 益昇, 石川 勉
1994 年 42 巻 1 号 p.
108-111
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A 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.
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河野 功, 岩本 千文, 亀田 由貴, 田中 隆, 楊 春〓
1994 年 42 巻 1 号 p.
112-114
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A 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.
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MINH DUC Nguyen, 笠井 良次, 大谷 和弘, 伊藤 優子, THOI NHAM Nguyen, 山崎 和男, 田中 治
1994 年 42 巻 1 号 p.
115-122
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Further 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-R
1 (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.
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森本 泰子, 細川 幹夫, 佐用 博照, 竹内 由和
1994 年 42 巻 1 号 p.
123-129
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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大塚 知子, 吉岡 澄江, 阿曽 幸男, 寺尾 允男
1994 年 42 巻 1 号 p.
130-132
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Utility 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.
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綿野 哲, 山本 明子, 宮南 啓
1994 年 42 巻 1 号 p.
133-137
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Effects 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.
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/ 手塚 康弘, 菊池 徹 /, Tohru KIKUCHI, Sutardjo SUPRIYATNA
1994 年 42 巻 1 号 p.
138-146
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Investigation 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.
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北 泰行, 前田 ひろし, 高橋 史江, 福井 誠二, 小川 利寿, 畑山 勝男
1994 年 42 巻 1 号 p.
147-150
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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藤井 澄三, 斎藤 徹, / [クヌギ] まゆり, Mayuri KUNUGI
1994 年 42 巻 1 号 p.
151-153
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
7-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 POCl
3-HCONMe
2) 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 MeNH
2. Similar cyclization between 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile (11c) and MeNH
2 yielded 7-benzyl-1-methyladenine (12c).
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井上 智弘, 小西 天二, 清沢 脩, 藤原 靖弘
1994 年 42 巻 1 号 p.
154-155
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Two 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).
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大塚 誠, 松田 芳久
1994 年 42 巻 1 号 p.
156-159
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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水野 恒政, 花森 雅裕, 秋本 恒一, 中川 寛, 荒川 勝雅
1994 年 42 巻 1 号 p.
160-162
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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-H
2O (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 D
2O in which the lifetime of singlet oxygen is about 10 times longer than in H
2O. 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).
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渡辺 善照, 神崎 [ヤスシ], 藤井 まき子, 松本 宜明, 塩崎 郁代, 田中 龍夫, 松本 光雄
1994 年 42 巻 1 号 p.
163-166
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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井上 博純, 仲村 進, 大塚 久男, 我伊野 三徳, 原田 恒博, 松木 健司, 武田 幹男
1994 年 42 巻 1 号 p.
167-172
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
The 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.
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上岡 龍一, 松本 佳人, 伊東 哲男, 松本 陽子, 加藤 康夫
1994 年 42 巻 1 号 p.
173-175
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A 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).
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加藤 良平, 高橋 治, 木曽 良明, 森口 郁生, 広野 修一
1994 年 42 巻 1 号 p.
176-178
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
Structures 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.
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正木 幸雄, 今枝 稔博, 河井 真
1994 年 42 巻 1 号 p.
179-181
発行日: 1994/01/15
公開日: 2008/03/31
ジャーナル
フリー
A 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).
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