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

MAMORU SUEKAWA ATSUSHI ISHIGE KAZUNORI YUASA KAZUHIKO SUDO MASAKI ABURADA EIKICHI HOSOYA

出版者

The Pharmaceutical Society of Japan

雑誌

Journal of Pharmacobio-Dynamics (ISSN:0386846X)

巻号頁・発行日

vol.7, no.11, pp.836-848, 1984 (Released:2008-02-19)

参考文献数

9

被引用文献数

91 181 242

---

General pharmacological studies were performed on (6)-gingerol and (6)-shogaol whhich are the pungent constituents of ginger (Zingiber officinale ROSCOE). Intravenous (i.v.) administration of (6)-gingerol (at 1.75-3.5 mg/kg) or (6)-shogaol (at 1.75-3.5 mg/kg) and oral administration of them (at 70-140 mg/kg) produced an inhibition of spontaneous motor activity, an antipyretic and analgesic effects, prolonged hexobarbital-induced sleeping time, and these effects of (6)-shogaol were mostly more intensive than that of (6)-gingerol. (6)-Shogaol showed an intense antitussive effect in comparison with dihydrocodeine phosphate. In the electro-encepharogram of cortex, the low amplitude fast wave pattern was observed for 5 min after i.v. administration of (6)-shogaol, and then changed to the drowsy pattern, which was restored after 60 min. In the gastro-intestinal system, (6)- shogaol intensively inhibited the traverse of charcoal meal through the intestine in contrast with (6)-gingerol after i.v. administration of 3.5 mg/kg, but (6)-shogaol facilitated such an intestinal function after oral administration of 35 mg/kg. Both (6)-shogaol and (6)-gingerol suppressed gastric contraction in situ, and the suppression by the former was more intensive than that by the latter. In the cardiovascular system, both (6)-shogaol and (6)-gingerol produced depressor response at lower doses on the blood pressure. At high doses, both drugs produced three phase pattern.

著者

加瀬 佳年

出版者

The Pharmaceutical Society of Japan

雑誌

Pharmaceutical Bulletin (ISSN:03699471)

巻号頁・発行日

vol.2, no.3, pp.298-299, 1954-09-25 (Released:2008-02-19)

被引用文献数

2 10

著者

Hirofumi MARUYAMA Keiko YAMAZAKI Sayuri MUROFUSHI Chihiro KONDA Tetsuro IKEKAWA

出版者

The Pharmaceutical Society of Japan

雑誌

Journal of Pharmacobio-Dynamics (ISSN:0386846X)

巻号頁・発行日

vol.12, no.2, pp.118-123, 1989 (Released:2008-02-19)

参考文献数

12

被引用文献数

22 35

---

Antitumor activity of Sarcodon aspratus (BERK.) S. ITO and Ganoderma lucidum (FR.) KARST. was investigated. Methanol and aqueous extracts of these Japanese mushrooms were tested for antitumor activity against solid type of sarcoma 180 by intraperitoneal or oral administration. The aqueous extract was remarkably effective for inhibition of tumor growth, but the methanol extract was not. The fraction of molecular weight more than 10000 had a high inhibitory activity against the tumor growth, but the fraction of molecular weight less than 10000 did not. Fractionation was carried out by using an ion-exchanger, and fraction S-4 having the highest carbohydrate content had the highest antitumor activity by intraperitoneal administration.

著者

ATTA-UR-RAHMAN Muhammad Iqbal CHOUDHARY Safdar HAYAT Abdul Majeed KHAN Aftab AHMED

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.49, no.1, pp.105-107, 2001 (Released:2002-03-29)

参考文献数

9

被引用文献数

41 55

---

Two new aurones, 4'-chloro-2-hydroxyaurone (1) and 4'-chloroaurone (2) were isolated from Spatoglossum variabile. The structures of these compounds were elucidated by modern spectroscopic techniques.

著者

Sang Hyun Sung So Young Kang Ki Yong Lee Mi Jung Park Jeong Hun Kim Jong Hee Park Young Chul Kim Jinwoong Kim Young Choong Kim

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.25, no.1, pp.125-127, 2002 (Released:2002-03-05)

参考文献数

14

被引用文献数

27 52

---

In the course of screening natural products for anti-acetylcholinesterase (AChE) activity, we found that a total methanolic extract of the underground parts of Caragana chamlague (Leguminosae) had significant inhibition towards AChE. Bioactivity-guided fractionation of the total methanolic extract resulted in the isolation and identification of two active stilbene oligomers, (+)-α-viniferin (1) and kobophenol A (2). Both 1 and 2 inhibited AChE activity in a dose-dependent manner, and the IC50 values of 1 and 2 were 2.0 and 115.8 µM, respectively. The AChE inhibitory activity of 1 was specific, reversible and noncompetitive.

著者

Kimio Higashiyama Yosuke Takeuchi Takayasu Yamauchi Satoshi Imai Junzo Kamei Yoshinori Yajima Minoru Narita Tsutomu Suzuki

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.28, no.5, pp.845-848, 2005 (Released:2005-05-01)

参考文献数

11

被引用文献数

11 14

---

We previously reported that either (+)-matrine (matridin-15-one) or (+)-allomatrine (the C-6 epimer of matrine)-induced antinociceptive effect was attenuated by s.c. pretreatment with a κ-opioid receptor (KOR) antagonist nor-binaltorphimine (nor-BNI), indicating the critical role of KORs in antinociceptive effects induced by these alkaloids. In the present study, we found that i.c.v. administration of either (+)-matrine- or (+)-allomatrine induced antinociceptive effects in the mouse tail-flick and warm-plate test, whereas these alkaloids when given spinally failed to induce antinociception. In the guanosine-5′-O-(3-[35S]thio)trisphosphate ([35S]GTPγS) binding assay, we demonstrated that neither (+)-matrine nor (+)-allomatrine produced the stimulation of [35S]GTPγS binding in the membranes of the spinal cord, indicating that (+)-matrine- and (+)-allomatrine-induced supraspinal antinociceptive actions was not due to a direct stimulation of KORs by these alkaloids. Therefore, we next investigated the involvement of dynorphin A (1-17) release at the spinal or supraspinal site in (+)-matrine- or (+)-allomatrine-induced antinociception. The i.c.v. pretreatment with an antiserum against dynorphin A (1-17) could not affect the antinociceptive effect induced by s.c. treatment of (+)-matrine. In contrast, the s.c.-administered (+)-matrine- and (+)-allomatrine-induced antinociceptive effect was significantly attenuated by i.t. pretreatment of an antiserum against dynorphin A (1-17). The present data suggest that either (+)-matrine or (+)-allomatrine when given i.c.v. may stimulate the descending dynorphinergic neuron, resulting in the stimulation of KORs in the spinal cord, and this phenomenon in turn produces the antinociception in mice.

著者

Noriaki Kawano Koji Ichinose Yutaka Ebizuka

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.25, no.4, pp.477-482, 2002 (Released:2002-07-10)

参考文献数

37

被引用文献数

30 40

---

Costus speciosus produces a large quantity of steroidal glycosides derived from the sole aglycone, diosgenin. Cycloartenol, a product of oxidosqualene cyclase (OSC), is postulated to be a common intermediate for phytosterols of primary metabolism and diosgenin of secondary metabolism, possibly providing a metabolic branch point. Two cDNAs, CSOSC1 and CSOSC2, were cloned from C. speciosus by RT-PCR and cDNA library screening. Both cDNAs encode 759 amino acids with high mutual identity (74%), resembling (>55% identity) the known OSCs. Phylogenetic tree analysis indicated that the gene products occupy distinct positions from those of cycloartenol synthases (CASs) and triterpene synthases from dicotyledonous plants. By functional expression in yeast, CSOSC1 and CSOSC2 were proved to encode a CAS and a multifunctional triterpene synthase, respectively. The present result is the first demonstration of the functional expression of OSCs from monocotyledonous plants.

著者

Yohei Kawano Masashi Nagata Takafumi Kohno Akihiro Ichimiya Tomomi Iwakiri Manabu Okumura Kazuhiko Arimori

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.35, no.3, pp.400-407, 2012-03-01 (Released:2012-03-01)

参考文献数

40

被引用文献数

17 19 7

---

Caffeine is thought to increase the antitumor effect of cisplatin or DNA-damaging agents because it is known that caffeine inhibits DNA repair. Caffeine-assisted chemotherapy has been used in the treatment of osteosarcomas. In addition, there are several reports about combination chemotherapy with caffeine for certain malignancies other than osteosarcomas. However, there are no reports that show the utility of combination chemotherapy with caffeine for hepatocellular carcinoma (HCC). We examined the combined effects of caffeine and cisplatin in human HCC cell lines, and screened for a more effective administration method of caffeine in vitro. Human HCC cell lines (HepG2, HLF, HuH-7, and Li-7) were exposed to caffeine (0—0.5 mM) and cisplatin (0—1.2 μg/mL) for 72 h, either alone or in combination. Cell numbers were measured by WST-8 assay, and cell apoptosis was determined by annexin V-fluorescein isothiocyanate (FITC)/propidium iodide (PI) binding assay. As a result, caffeine increased the antitumor effect of cisplatin on cell proliferation and cell apoptosis in the HCC cell lines. Moreover, this effect was dependent on the amount of exposure to caffeine. These results suggest that caffeine-assisted chemotherapy is useful for HCC treatment.

著者

Hiroyuki Tsutsumi Yoshifumi Kinoshita Takashi Sato Takashi Ishizu

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.8, pp.1008-1015, 2011-08-01 (Released:2011-08-01)

参考文献数

28

被引用文献数

12 13 5

---

Crystals of the complexes of (+)-catechin (CA) of non-galloylated catechin and (−)-catechin-3-O-gallate (Cg) of galloylated catechin with caffeine were prepared, and their stereochemical structures and intermolecular interactions were determined by X-ray crystallographic analysis. CA formed a 1 : 1 complex with caffeine by intermolecular hydrogen bonds, whereas Cg formed a 1 : 2 complex with caffeine, which was formed by face-to-face and offset π–π interactions and intermolecular hydrogen bonds. A solution of two kinds of non-galloylated catechin, CA and (−)-epicatechin (EC), and caffeine (molar ratio 1 : 1 : 2) in water afforded a 1 : 1 : 2 complex, the crystal structure of which had two layers, one layer in which CA and caffeine formed alternate lines and an other layer in which EC and caffeine formed alternate lines. The 1 : 1 : 2 complex was formed by offset π–π and CH–π interactions and intermolecular hydrogen bonds.

著者

In-sok Hwang Juneyoung Lee Dong Gun Lee

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.34, no.10, pp.1602-1608, 2011-10-01 (Released:2011-10-01)

参考文献数

36

被引用文献数

8 13

---

Cruciferous vegetables contain glucobrassicin which, during metabolism, yields indole-3-carbinol (I3C). The aim of this study was to find whether indole-3-carbinol caused apoptosis and its mechanism in Candida albicans. We found that treatment of Candida albicans with indole-3-carbinol significantly increased the reactive oxygen species and hydroxyl radical accumulation. The hydroxyl radical is one of the most active components of oxygen, and it is the end product of an oxidative damage cellular death pathway. We investigated the general phenotypes of apoptosis and then investigated whether there were other distinct markers of apoptosis. Furthermore, the effects of thiourea as a hydroxyl radical scavenger and protective effect of trehalose, which is the result of the fungal immune system, was also assured. This study indicates that indole-3-carbinol has apoptosis effects, including a production of hydroxyl radicals, cytochrome c release and activation of metacaspase. Both hydroxyl radicals and metacaspases triggered apoptosis in Candida albicans.