著者

末宗 洋 岩崎 源司 上野 貢嗣 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.11, pp.4632-4636, 1984-11-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

2 5

---

The chemical conversion of (+)-limonene (1) and (-)-perillyl alcohol (10) into 9-substituted p-mentha-1, 8 (10)-diene derivatives is described. The lithiated species of 1 and 10 were easily obtained in good yields, by using sec-butyl lithium in N, N, N', N'-tetramethylethylenediamine. The reaction of the lithiated species (A and B) with various electrophiles was completed within 1-2 h to give 9-substituted p-mentha-1, 8 (10)-diene derivatives. The stereochemistry of the chiral center of the starting material was retained in the products. 9-Hydroxy-p-mentha-1, 8 (10)-diene (8) was also obtained by another short sequence of steps. Oxidation of the phenylthio derivative (7) gave the sulfoxide (9). Treatment of 9 with trimethyl phosphite afforded 8.

著者

上野 貢嗣 末宗 洋 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.9, pp.3768-3769, 1984-09-25 (Released:2008-03-31)

参考文献数

3

被引用文献数

4 12

---

The key intermediate (11) for the synthesis of carbacyclin (1) was synthesized by the application of a new method for stereoselective five-membered ring formation using Wilkinson complex.

著者

Mi Kyoung Kim Tae-Gum Lee Minji Jung Ki-Ho Park Youhoon Chong

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.66, no.11, pp.1019-1022, 2018-11-01 (Released:2018-11-01)

参考文献数

17

被引用文献数

12

---

Upon single treatment against Staphylococus aureus, quercetin–pivaloxymethyl conjugate (Q-POM) had antibacterial activities with minimum inhibitory concentrations (MICs) of 16–32 mg/L. Q-POM showed MIC of 32 mg/L against vancomycin-resistant Enterococcus faceium (VRE), which is remarkably lower than other antibiotics investigated (≥256 mg/L). Under sub-MIC concentrations, Q-POM potentiated the activity of ampicillin, cefepime, and vancomycin against S. aureus and Enterococcus (including highly resistant strains such as hetero-resistant vancomycin-intermediate S. aureus (hVISA), vancomycin-intermediate S. aureus (VISA), and VRE), by decreasing the MICs of these antibiotics by 4–128 folds. Q-POM was found to be partially synergistic with ampicillin and cefepime against S. aureus and Enterococcus, while it was strongly synergistic with vancomycin. Q-POM at 5 mg/L inhibited the formation of biofilms of S. aureus by 24–83% and VRE by 70%. Additionally, Q-POM inhibited the hemolytic activity of S. aureus in a dose-dependent manner. Cytotoxic activity was evaluated in human liver epithelial cells (HepG2), and the 50% cytotoxicity concentration (CC50) value of Q-POM was higher than 50 mg/L. These results indicate the potential use of Q-POM in treatment of methicillin-resistant Staphylococcus aureus (MRSA) and VRE infections.

著者

甲斐 麻美子 野田 敦子 野田 浩司 後藤 茂

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.9, pp.3604-3608, 1988-09-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

8 11

---

This study was undertaken to evaluate the relationship between the structure and monoamine oxidase (MAO) inhibitory activity of a new series of tricyclic compounds, represented by tetrazolo-[5, 1-a]phthalazine (Tetra-P), which are based on the pentanthrene skeleton (Fig. 1.). Eleven tricyclic compounds analogous to Tetra-P were synthesized and tested as MAO inhibitors in vitro. Some of them, 1, 2, 3-triazolo[1, 5-a]quinoline (Tri-Q), tetrazolo[5, 1-a]isoquinoline (Tetra-I), 1, 2, 3-triazolo-[5, 1-a]isoquinoline (Tri-I2) and 1H-naphtho[1, 2-d]triazole (Tri-N), were found to have potent MAO inhibitory effects almost equal to that of iproniazid or nialamide. In this series of compounds, the addition of the C ring to the bicyclic skeleton seemed to produce an increase in MAO inhibitory potency compared with the corresponding bicyclic compounds. The sequence of nitrogen atoms of the C ring appeared to be important for the MAO inhibitory effect. It was concluded that the electronic conditions around the C ring are critical for the interaction between MAO and these inhibitors.

著者

甲斐 麻美子 野田 敦子 野田 浩司 後藤 茂

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.12, pp.5585-5588, 1985-12-25 (Released:2008-03-31)

参考文献数

6

被引用文献数

5 6

---

A new series of monoamine oxidase (MAO) inhibitors structurally analogous to tetrazolo [5, 1-a] phthalazine (Tetra-P) was detected using rat brain mitochondrial MAO. In the tricyclic group, naphtetrazole (NTE) indicated a marked potency of MAO inhibition almost equal to that of iproniazid, and naphtriazole (NTR) showed similar potency as did Tetra-P. The nonselective and competitive inhibition for both types, MAO-A and MAO-B, was observed in some Tetra-P analogues.

著者

西村 卓三 清水 文治 岩井 一成

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.11, no.11, pp.1470-1472, 1963-11-25 (Released:2008-03-31)

被引用文献数

35 55

著者

Shu-Hua Qi Si Zhang Cheng-Hai Gao Qin-Xing Li

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.58, no.6, pp.884, 2010-06-01 (Released:2010-06-02)

被引用文献数

2 3

著者

Hajime KATAYAMA Yusuke KAWADA Kimiyoshi KANEKO Takamitsu OSHIYAMA Noriyuki TAKATSU

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.47, no.1, pp.48-53, 1999-01-15 (Released:2008-03-31)

参考文献数

31

被引用文献数

9 17

---

A new type of synthetic inhibitor of DNA topoisomerase I and II was examined and several of these derivatives exhibited strong dual activity against these enzymes. This series of compounds showed high cytotoxic activities against cancer cells, but only a limited number of compounds showed any noticeable activity in an in vivo test against murine P388. Non-specific toxicity was observed in the in vivo tests.

著者

Judith RAZAFIMBELO Genevieve BAUDOUIN Francois TILLEQUIN Pierre RENARD Stephane LEONCE Alain PIERRE Ghanem ATASSI

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.46, no.1, pp.34-41, 1998-01-15 (Released:2008-03-31)

参考文献数

33

被引用文献数

3 4

---

Condensation of 5-amino, 6-amino, 7-amino and 8-amino-2, 2-dimethyl-2H-chromenes with either 6-bromo-veratraldehyde or 6-chloropiperonal afforded the corresponding Schiff bases, which were subsequently reduced to the corresponding benzylchromenylamines 30-33 and 36-39. Lithium diisopropylamide-mediated cyclization of those amines, followed by spontaneous air oxidation, afforded pyranophenanthridines 3-14. The cytotoxicity of compounds 3-14 was evaluated against L1210 and HT29 cell lines. 9, 9-Dimethyl-9H-pyrano[3, 2-b]phenanthridines appear to be the most promising compounds of the series, since both the dimethoxy derivative 11 and the methylenedioxy derivative 12 exhibit significant cytotoxic activity. Compound 12 was the most active and induced a massive accumulation of cells in G2+M phases, suggesting that the cytotoxicity is due to a perturbation of the integrity or function of DNA.

著者

山脇 一郎 鈴木 雅博 小川 和男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.42, no.4, pp.963-971, 1994-04-15 (Released:2008-03-31)

参考文献数

23

被引用文献数

1 1

---

Piperazinealkanol ester derivatives of indomethacin were prepared and tested for inhibitory activities against 5-lipoxygenase (5-LO) and cyclooxygenase (CO). They inhibited 5-hydroxyeicosatetraenoic acid (5-HETE) formation by the cytosol of guinea pig polymorphonuclear leukocytes and thromboxane B2 (TXB2) formation by washed rabit platelet suspension. Of the test compounds, 2-[4-(2-hydroxyethyl)-1-piperazinyl]-1-phenylethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate dimaleate (II-8) was found to be the most active dual inhibitor of 5-LO and CO, and its inhibitory potency was higher than that of 2-[4-(3-hydroxypropyl)-1-piperazinyl]-ethyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl]-3-indolylacetate (CR-1015) (I), the lead compound.

著者

秋山 稔 大石 順一 白井 孝 明石 景泰 吉田 浩一 錦戸 条二 林 絋 白淵 穣 西村 大吉 伊藤 平隆 渋屋 千征 石田 寅夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.26, no.3, pp.981-984, 1978-03-25 (Released:2008-03-31)

被引用文献数

14 21

---

In order to obtain 1-β-D-arabinofuranosylcytosine derivatives with better antitumor effect, 12 kinds of saturated fatty acyl groups were introduced at the N4-position of 1-β-D-arabinofuranosylcytosine. The presence of a great excess of water and about two-fold equivalents of carboxylic anhydride was found to be most desirable for selective N4-acylation. This simple method of one-step N4-acylation should be generally applicable to cytosine nucleosides and a variety of carboxylic anhydrides.

著者

赤羽 健司 永野 泰夫 梅山 秀明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.1, pp.86-92, 1989-01-25 (Released:2008-03-31)

参考文献数

26

被引用文献数

4 8

---

Two empirical indices accounting for the hydrophobic interaction are described. The first index is a "hydrophobic field-effect (Hf) index, "which indicates the hydrophobic nature of the binding site of a host molecule such as an enzyme, and the second index is a "hydrophobic correlation (Hc) index", which indicates the hydrophobic correspondency between a host molecule and its guest molecule such as a ligand. Furthermore, a method to calculate the surface area of a molecule is described, in which the molecular surface is treated as a set of area-preserving spherical triangles. The hydrophobic effects on the interaction between papain and its inhibitor benzyloxycarbonyl-L-phenylalanyl-L-alanyl-methylene (Z-Phe-Ala-CH2-), which is covalently bound to catalytic Cys Sγ of the enzyme, were investigated by using these indices. It is quantitatively shown that the binding sites interacting with the benzene rings of P2 Phe and P3 Z are more hydrophobic, while the site of the carbonyl group of P1 Ala is more hydrophilic. The substrate specificity of papain can be explained in part by these indices. Both the Hc and Hf indices are visualized by using computer graphics. These indices would be useful as quantitative structure-activity relationship (QSAR) parameters.

著者

Yasuki YAMADA Koji ANDO Yukishige IKEMOTO Hiroki TADA Eiji SHIRAKAWA Eiji INAGAKI Saizo SHIBATA Ikuro NAKAMURA Yoshiharu HAYASHI Kiyoteru IKEGAMI Itsuo UCHIDA

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.45, no.10, pp.1631-1641, 1997-10-15 (Released:2008-03-31)

参考文献数

32

被引用文献数

4 4

---

A series of renin inhibitors containing the (2S, 3S, 5S)-2-amino-1-cyclohexyl-6-methyl-3, 5-heptanediol (2-amino-3, 5-anti-diol) fragment as a novel transition-state mimic was synthesized, and their biological activities were evaluated. All of the synthesized compounds containing the 2-amino-3, 5-anti-diol fragment at the P1-P1' position showed high in vitro renin-inhibitory activity with IC50 values in the 10-8-10-10M range, and most of them caused a reduction of blood pressure when administered orally to salt-depleted, conscious marmosets. The inhibitor (29) with the 4-hydroxypiperidine residue at the P4 position showed the highest activity in terms of both potency and duration of the blood pressure-lowering effect.

著者

赤羽 健司 上條 哲聖 飯塚 欣二 田口 武夫 小林 義郎 木曽 良明 梅山 秀明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.9, pp.3447-3452, 1988-09-25 (Released:2008-03-31)

参考文献数

31

被引用文献数

3 4

---

The structure-activity relationship of acyl-His-trifluorinated leucinol derivatives as inhibitors of human renal renin is discussed based upon the tertiary structure of human renin, which was deduced from the crystal structure of penicillopepsin by assuming structural similarity. The structural requirements for the inhibitors and possible interactions at the renin binding site are discussed.

著者

飯塚 欣二 上條 哲聖 原田 弘 赤羽 健司 久保田 哲弘 島岡 巌 梅山 秀明 木曽 良明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.6, pp.2278-2281, 1988-06-25 (Released:2008-03-31)

参考文献数

11

被引用文献数

4 4

---

New human renin inhibitors were designed from transition-state analogues of angiotensinogen, synthesized and evaluated. The peptide derovative, which contained 1-naphthylmethylsuccinylamide residue (P3) with a retro-inverso amide bond and a norstatine isoamylamide residue (P1-P1'), was stable to proteases and had potent human renin inhibitory activity. This compact inhibitor exhibited hypotension when administered orally to a monkey.

著者

飯塚 欣二 上條 哲聖 原田 弘 赤羽 健司 久保田 哲弘 江藤 裕夫 島岡 厳 椿 敦 村上 真 山口 敏章 伊與部 亮 梅山 秀明 木曽 良明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.9, pp.2487-2493, 1990-09-25 (Released:2008-03-31)

参考文献数

33

被引用文献数

7 11

---

The synthesis and the structure-activity relationships of renin inhibitors designed from the angiotensinogen transition state are described. These inhibitors contained residues modified at P1-P1, , P2, and P4-P3. Decrease in the size of side chain alkyl group in norstatine analog at P1 diminished the inhibitory activities of the compounds. Compound 5j, which contained valine residue instead of histidine residue at P2, inhibited potently cathepsin D (IC50=6.0×10-9 M) and pepsin (IC50=3.5×10-7 M) to the same extent as renin (IC50=8.5×10-10 M), and thus was not specific for renin. The reduction of the β-carbonyl group to methylene group in β-carbonylpropionyl residue at P4-P3 decreased the potency about 2 orders against human renin (5i : IC50=1.1×10-7 M vs. 1 : IC50=2.4 ×10-9 M). These results confirmed the rationality of our analysis of the interaction between an orally potent human renin inhibitor 1 and the active site of human renin using modeling techniques, showing that 1 fits the active site of renin favorably. The experimental details of the synthesis are presented.

著者

富田 真雄 新宮 徹朗 冨士谷 憲徳 古川 宏

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.13, no.8, pp.921-926, 1965-08-25 (Released:2008-03-31)

被引用文献数

25 32

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The proton magnetic resonance spectra of N-methylcoclaurine type bases were examined and assignment of the alkoxyl groups and aromatic protons was presented. Correlations of the Chemical shifts with stereochemistry of the molecule were discussed.

著者

袖岡 幹子 小川 裕司 間瀬 俊明 柴崎 正勝

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.3, pp.586-598, 1989-03-25 (Released:2008-03-31)

参考文献数

48

被引用文献数

11 19

---

An efficient and useful synthesis of isocarbacyclins, potent carbon analogs of Prostacyclin(PGI2), has been accomplished.Three synthetic routes to isocarbacyclins using intramolecular thermal ene reaction or intramolecular aldol condensation as a key step are described.

著者

伊関 克彦 間瀬 俊明 岡崎 徳二 柴崎 正勝 池上 四郎

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.12, pp.4448-4455, 1983-12-25 (Released:2008-03-31)

参考文献数

21

被引用文献数

7 9

---

Biologically interesting 9 (O)-methano-△6-prostaglandin I1 (9 (O)-methano-△6-PGI1), a chemically stable analog of prostacyclin (PGI2), was efficiently synthesized from 1, 3-cyclooctadiene with high stereo- and regiochemical control. In all three biological test systems examined, 9 (O)-methano-△6-PGI1 was found to be considerably less active than prostaglandin E1 (PGE1).

著者

長尾 善光 萩原 裕一 山田 省三 落合 正仁 藤田 榮一

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.11, pp.4686-4689, 1984-11-25 (Released:2008-03-31)

参考文献数

15

被引用文献数

3 4

---

As a new extention of monitored aminolysis of 3-acyl-1, 3-thiazolidine-2-thione (ATT), a convenient procedure for the synthesis of αβ-unsaturated carboxylic acid amides has been developed using a new hetero-bifunctional reagent, 3-dimethylphosphonoacetyl-1, 3-thiazolidine-2-thione (DMPATT). DMPATT was effectively used as the bridging reagent between amino (or imino) compounds and aldehydes (or ketone) to afford various olefinic amides in good yields.