著者

斉藤 仁 好川 博 西村 吉雄 近藤 信一 竹内 富雄 梅澤 濱夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.34, no.9, pp.3733-3740, 1986-09-25 (Released:2008-03-31)

参考文献数

42

被引用文献数

8 14

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D-(and L-)Aminoglycosidic variants of 4'-O-demethyl-1-epipodophyllotoxin were synthesized by glycosidation of 4'-O-benzyloxycarbonyl- or 4'-O-chloroacetyl-4'-O-demethyl-1-epipodophyllotoxin (8 or 22) with the corresponding aminosugar derivatives. Cyclic acetals of 1-O-(2-amino-2-deoxy- and 3-amino-3-deoxy-β-D-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxins (13 and 21) gave a significant survival time increase in mice with leukemia L-1210, and showed superior activity to VP-16-213 (etoposide, 5).

著者

埜渡 裕義 黒田 泰男 速水 宏 岡本 一也 浴本 久雄 高橋 克俊

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.9, pp.2406-2409, 1989-09-25 (Released:2008-03-31)

参考文献数

15

被引用文献数

14 18

---

Novel alkyl-1, 4-butanediamine Pt(II) complexes having a seven-membered ring structure were synthesized and characterized by fast atom bombardment mass and infrared spectra and elemental analysis. Their antitumor activities in vivo toward lymphoid leukemia L1210 and LEwis lung carcinoma LL were studied in the case where the leaving group was either dichloride or cyclobutane-1, 1-dicarboxylate. 1, 4-Butanediamine Pt(II) complexes (seven-membered ring) showed higher antitumor activities than those of ethylenediamine Pt(II)(five-membered ring) and 1, 3-propanediamine Pt(II)(six-membered ring) complexes toward L1210 for both leaving groups. Alkyl-1, 4-butanediamine Pt(II) complexes showed high antitumor activities toward L1210, except for 1, 1-dimethyl-1, 4-butanediamine Pt(II) complexes. In particular, 2, 2-dimethyl-1, 4-butanediamine and 2, 3-dimethyl-1, 4-butanediamine Pt(II) complexes exhibited excellent antitumor activities with T/C% values higher than 300. None of the dichloro Pt(II) complexes showed antitumor activities toward LL, but the cyclobutane-1, 1-dicarboxylato Pt(II) complexes, which were moderately active toward L1210 with T/C% values aroung 200, also showed high antitumor activities toward LL with T/C% values of more than 200. Alkyl-1, 4-butanediamine Pt(II) complexes with a seven-membered ring structure were found to be stable and to have antitumor activities in vivo.

著者

Hidetoshi Nakatake Hisao Ekimoto Mariko Aso Atsushi Ogawa Asami Yamaguchi Hiroshi Suemune

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.59, no.6, pp.710-713, 2011-06-01 (Released:2011-06-01)

参考文献数

20

被引用文献数

9 17

---

Bisphosphonates have high affinity for hydroxyapatite (HA), which is abundantly present in bone. Also, platinum complexes are known that have a wide spectrum of antitumor activities. The conjugate of bisphosphonate and a platinum complex might have HA affinity and antitumor activity, and become a drug for metastatic bone tumor. In this study, the authors synthesized platinum complexes that had dialkyl bisphosphonic acid as a ligand, and evaluated the possibility of the synthesized complexes as a drug for metastatic bone tumor. The synthesized dialkyl bisphosphonate platinum(II) complex was characterized, and its stability in an aqueous solution was also confirmed. The synthesized platinum complex showed higher HA affinity than other platinum complexes such as cisplatin and carboplatin in an experiment of adsorption to HA. In vitro, the platinum complex showed tumor growth inhibitory effect stronger than or equal to cisplatin, which is the most commonly used antitumor agent. Moreover, the platinum complex showed a bone absorption inhibitory effect on the osteoclast. These results suggest potential of dialkyl bisphosphonate platinum(II) complexes as a drug for metastatic bone tumor.

著者

門田 重利 高森 靖 / 菊池 徹 田中 謙 浴本 久雄 Hisao EKIMOTO

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.10, pp.2687-2697, 1990-10-25 (Released:2008-03-31)

参考文献数

22

被引用文献数

28 54

---

Woodfruticosin (woodfordin C), a new cyclic dimeric hydrolyzable tannin having an inhibitory activity toward deoxyribonucleic acid (DNA) topoisomerase II, has been isolated from the leaves of Woodfordia fruticosa KURZ (Lythraceae) along with three known flavonol glycosides and three known flavonol glycoside gallates. The structure of woodfruticosin (woodfordin C) was determined by the use of two-dimensional nuclear magnetic resonance (2-D NMR) spectroscopy including heteronuclear multiple quantum coherence (HMQC) and heteronuclear mucltiple bond connectivity (HMBC) techniques. Detailed analyses of the proton and carbon-13 NMR (1H-and 13C-NMR) spectra of six known flavonoids were performed.

著者

松田 彰 伊藤 弘子 竹貫 健二 佐々木 琢磨 上田 亨

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.3, pp.945-953, 1988-03-25 (Released:2008-03-31)

参考文献数

21

被引用文献数

32 55

---

The reaction of 4-ethoxy-1-(3, 5-O-tetraisopropyldisiloxanyl-1, 3-diyl-β-D-erythro-pentofuran-2-ulosyl)-2(1H)-pyrimidinone (11) with various organometallic reagents yielded corresponding 2'-branched-chain sugar pyrimidine nucleosides. Only in the reactions with MeMgBr and EtMgBr was the more hindered β-attack observed to afford and 2'-alkyl ribofuranosides (13a, b). In the reaction of 11 with MeLi, Me3, Al, or PhMgBr, 2'-methyl or phenyl arabinosides (12a, b, c)were obtained stereoselectively. Conversion of these pyrimidine nucleosides into cytosine derivatives is also described and their antileukemic and antiviral activities are discussed.

著者

Tetsuji Noguchi Naoki Tanaka Toyoki Nishimata Riki Goto Miho Hayakawa Atsuhiro Sugidachi Taketoshi Ogawa Yoichi Niitsu Fumitoshi Asai Tomoko Ishizuka Koichi Fujimoto

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.57, no.1, pp.22-33, 2009-01-01 (Released:2009-01-01)

参考文献数

25

被引用文献数

10 13

---

To develop a novel and effective anticoagulant with potent and selective factor Xa (FXa) inhibitory activity, a new series of cinnamyl derivatives with enhanced lipophilicity and prodrug forms were synthesized and their biological activities were evaluated. As a result, we found that cinnamyl derivative (N-{4-[1-(acetimidoyl)piperidin-4-yloxy]-3-carbamoylphenyl}-N-[(Z)-3-(3-amidinophenyl)-2-fluoro-2-propenyl]sulfamoyl)acetic acid dihydrochloride (26d, R-142086) with a fluorine atom on the double bond exhibited potent anticoagulant activity and no mutagenic potential. Moreover, orally administered R-142086 exhibited potent anti-FXa activity and anticoagulant activity in dogs.

著者

Naoki TANAKA Riki GOTO Rie ITO Miho HAYAKAWA Taketoshi OGAWA Koichi FUJIMOTO

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.4, pp.639-646, 1998-04-15 (Released:2008-03-31)

参考文献数

14

被引用文献数

2 2

---

A series of [2-(ω-phenylalkyl)phenoxy]alkylamines was synthesized and their 5-hydroxytryptamine2 (5-HT2) and/or dopamine2 (D2) receptor antagonistic activities were examined in vitro. [2-(4-Phenylbutyl)phenoxy]alkylamines showed strong inhibition of both 5-HT2 and D2 receptors. It particular, [2-(4-phenylbutyl)phenoxy]-methylpiperidine derivatives, 10b, 10i and 10q, exhbited potent inhibition. The structure-activity relationships in this series of compounds are discussed.

著者

Naoki TANAKA Riki GOTO Miho HAYAKAWA Atsuhiro SUGIDACHI Taketoshi OGAWA Fumitoshi ASAI Koichi FUJIMOTO

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.48, no.2, pp.245-255, 2000-02-01 (Released:2008-03-31)

参考文献数

26

被引用文献数

4 5

---

A series of [2-(ω-phenylalkyl)phenoxy]alkylamines was synthesized and thir receptor binding affinity was examined in vitro. These compounds showed an affinity for serotonin-2 (5-HT2) and dopamine-2 (D2) receptors. [2-(2-phenylethyl)phenoxy]alkylamine derivatives with a pyrrolidine or piperidine moiety in the structure showed higher affinity for 5-HT2 receptors but lower affinity for D2 receptors. Among these compounds, (S)-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]1-methylpyrrolidine, (S)-27, exhibited the most potent and selective affinity for 5-HT2 receptors. Furthermore, (S)-27 was effective in inhibiting 5-HT-induced vasoconstriction in vitro and platelet aggregation both in vitro and ex vivo.

著者

末宗 洋 田中 直樹 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.38, no.11, pp.3155-3157, 1990-11-25 (Released:2008-03-31)

参考文献数

6

被引用文献数

6 6

---

Diastereoselective acetalization of methyl pyruvate and methyl phenylformate with (R)-1, 3-butanediol afforded predominantly (2R, 4R)-2-methoxycarbonyl-2, 4-dimethyl (or 4-methyl-2-phenyl)-1, 3-dioxanes (1a, 4a) under thermodynamically controlled conditions. The (2S, 4R)-isomer (1b) was obtained as the major product under kinetically controlled conditions.

著者

佐伯 清太郎 山下 絢子 盛中 泰洋 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.25, no.1, pp.79-86, 1977-01-25 (Released:2008-03-31)

被引用文献数

1 2

---

1, 1-Ethylenedioxy-9-(2-pyridyl) quinolizidine (1) was converted to N-ethoxycarbonylpyridinium salt (3) via monohydrobromide (2) by successive treatment with ammonium bromide and ethyl bromoacetate. The reaction of 3 with hydrochloric acid was markedly affected with the concentration of the acid. Thus, when 3 was heated with 15-20% hydrochloric acid, ring closure took place accompanied by hydrolysis of the ketal and ester groups and also decarboxylation to give 17-hydroxy compound (4). Heating with triethylamine gave dehydrated pyridinium salt (5) which was reduced with sodium borohydride and then catalytically to dl-allomatridine (6). On the other hand, heating 3 with 5-10% hydrochloric acid gave a carboxylic acid (9) which was also transformed into 6 through an ester (10) and a ring closure product (11) as shown in Chart 2. The action of 30% acid on 3 followed by the similar treatments afforded 1-hydroxy-9-(2-pyridyl) quinolizidine (7). Transformation of 1 to 17-hydroxyallomatridine (8) was further achieved successively by hydrolysis to 1-oxo compound (12), formation of its cyanohydrin (13) and hydrogenation over Raney nickel.

著者

安澤 亨 飯田 孝男 室井 健一 市村 通朗 高橋 恵一 佐野 浩

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.3728-3731, 1988-09-25 (Released:2008-03-31)

参考文献数

2

被引用文献数

54 72

---

The structures of new antitumor antibiotics, Duocarmycin A, C1 and C2, isolated from the culture broth of Streptomyces sp., have been determined on the basis of chemical and physicochemical evidence.

著者

池原 森男 三木 弘子

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.8, pp.2449-2453, 1978-08-25 (Released:2008-03-31)

被引用文献数

23 36

---

9-(2'-O-Methanesulfonyl- or trifluoromethanesulfonyl-3', 5'-di-O-tetrahydropyranyl-β-D-arabinofuranosyl) adenine (Ia, b) were reacted with lithium chloride or tetrabutylammonium halide to yield 2'-halogeno-2'-deoxy compounds (IIa-d). These halogeno compounds were deprotected with 80% acetic acid to give 2'-chloro-, 2'-bromo-, 2'-fluoro and 2'-iodo-2'-deoxyadenosine (IVa-d) in overall yields of 12-25% from the compound I. Ultraviolet absorption properties, 1H and 13C-nuclear magnetic resonance spectral properties were recorded on the compounds IVa-d.

著者

金子 正勝 木村 美佐子 清水 文治 矢野 純一 池原 森男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.25, no.8, pp.1892-1898, 1977-08-25 (Released:2008-03-31)

被引用文献数

2 2

---

9-(β-D-Arabinofuranosyl) adenine 5'-phosphate was obtained from adenosine 5'-phosphate via the novel intermediate 8, 2'-O-cycloadenosine 5'-phosphate. In contrast to the synthesis of 9-(β-D-arabinofuranosyl) adenine, it was difficult to cleave this compound by hydrogen sulfide directly to 8, 2'-O-cycloadenosine 5'-phosphate because of a considerable degree of dephosphorylation. However N-acylated 8, 2'-O-cycloadenosine 5'-phosphate was readily cleaved at the cyclo-bond by hydrogen sulfide. Desulfurization of 8-mercapto-9-(β-D-arabinofuranosyl) adenine 5'-phosphate gave the desired pure crystalline product.'

著者

佐藤 章 今井 良二 中溝 喜博 平田 正

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.27, no.3, pp.765-770, 1979-03-25 (Released:2008-03-31)

被引用文献数

2 5

---

Guanine and xanthine nucleoside derivatives (3, 4 and 6) bearing nitrosourea functional groups were synthesized from guanine nucleoside ureas (2) obtained by the reaction of 2'-deoxy-2'-aminoguanosine (1) with isocyanates and their antitumor activity against sarcoma-180 solid tumor and leukemia L-1210 were determined. Among the compounds tested, 2'-deoxy-2'-[3-(2-chloroethyl)-3-nitrosoureido]-xanthosine (4b) found to have the most potent activity. Moreover, very slight decrease in white blood cells of mice bearing sarcoma-180 solid tumor was observed after administration of 4b.

著者

金井 貞 小嶋 孝志 丸山 修 市野 元信

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.18, no.12, pp.2569-2571, 1970-12-25 (Released:2008-03-31)

被引用文献数

10 17

著者

小菅 卓夫 辻 邦郎 平井 孝一 福山 俊典

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.7, pp.3059-3061, 1985-07-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

20 35

---

A Coryneform bacterium, isolated from the digestive gland of the Japanese ivory shell, Babylonia japonica, was shown to produce neosurugatoxin and prosurugatoxin, the causative toxins of a food poisoning outbreak in 1965 following ingestion of the shellfish. This is the first evidence that marine toxins may be produced by bacteria.

著者

枡井 雅一郎 原 晴次郎 上嶋 孝博 川口 哲央 尾崎 茂子

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.11, pp.4209-4211, 1983-11-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

12 61

---

Benzylic, allylic carbons and the carbon α to hetero atoms are electrochemically oxidized to the corresponding carbonyl group in the presence of N-hydroxyphthalimide under mild conditions.

著者

枡井 雅一郎 細見 克子 土田 圭一 尾崎 茂子

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.11, pp.4798-4802, 1985-11-25 (Released:2008-03-31)

参考文献数

32

被引用文献数

15 46

---

Electrochemical oxidation of olefins using N-hydroxyphthalimide as a mediator was studied. Allylic methylene and allylic methine groups were oxidized to give the corresponding enones, while allylic methyl groups were not readily oxidized except for those of 2, 3-dimethyl-2-butene. The product distribution was similar to that observed in free radical autoxidation of olefins. A possible mechanism of the oxidation is proposed.

著者

Masateru Ono Chikako Masuoka Mihoko Koto Michiko Tateishi Haruki Komatsu Hiromasa Kobayashi Keiji Igoshi Yasuyuki Ito Masafumi Okawa Toshihiro Nohara

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.50, no.10, pp.1416-1417, 2002 (Released:2002-10-01)

参考文献数

6

被引用文献数

5 10

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A new ortho-benzoyloxyphenyl acetic acid ester, called vaccihein A (1), was isolated from the fruit of rabbiteye blueberry (Vaccinium ashei). The chemical structure was determined on the basis of spectroscopic data. Compound 1 had antioxidative activity using the ferric thiocyanate method. In addition, 1 showed a scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl.

著者

SHOHGO ATARASHI SHUICHI YOKOHAMA KEN-ICHI YAMAZAKI KATSU-ICHI SAKANO MASAZUMI IMAMURA ISAO HAYAKAWA

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.5, pp.1896-1902, 1987-05-25 (Released:2009-10-19)

参考文献数

14

被引用文献数

46 99

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Two optically active (100% enantiomeric excess) isomers (13a and 13b) of ofloxacin (1) [(±) -ofloxacin; DL-8280; (±) -9-fluoro-2, 3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-7H-pyrido [1, 2, 3-de] [1, 4] benzoxazine-6-carboxylic acid] and their fluoromethyl derivatives (14a and 14b) were prepared via their optically active intermediates resolved by use of high-performance liquid chromatography (HPLC). The isomers (13a and 13b) were also obtained efficiently by an alternative route via separation of the diastereoisomers (18, 19) prepared in the reaction of benzoxazine (17) with L-prolinyl chloride.The (-) -isomers of 1 and its fluoromethyl derivative (2) were approximately twice as active as the corresponding racemates, while the (+) -isomers were considerably less active than the racemates.The absolute configuration at the C3 position in the oxazine ring in a series of (-) -compounds (b) was confirmed by X-ray analysis of the hydrochloride of the (-) -benzoxazine derivative (15b) to be S.