著者

肥塚 美千代 方 成林 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.37, no.5, pp.1185-1187, 1989-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

9 12

---

1, 4-Addition of organocopper reagents to γ-substituted α, β-unsaturated γ-lactones followed by intramolecular trapping of the resulted enolates afforded cis, cis-1, 2, 3-trisubstituted cyclopentanes and cyclohexanes in a stereocontrolled manner. This new cyclization reaction to cyclopentanes provides a new synthetic route to the key intermediate in the synthesis of 11-deoxyprostaglandins.

著者

肥塚 美千代 林 教行 鎌下 知子 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.36, no.4, pp.1550-1553, 1988-04-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

13 14

---

2, 6-Dioxabicyclo[3.3.0]octan-3, 7-dione seems to be a promising compound for the synthesis of natural products such as epoxyeicosatrienoic acid, laurediol, and eldanolide. This compound, consisting of two γ-lactones, could be prepared by double lactonization of the silver salt of trans-3-hexenedioic acid using iodine. Starting with this bis-lactone, (±)-eldanoide could by synthesized in a stereocontrolled manner.

著者

福川 清史 周東 智 平野 孝夫 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.34, no.9, pp.3653-3657, 1986-09-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

4 11

---

Photolysis of 1-β-D-ribofuranosyl-5-aminoimidazole-4-carboxamide (AICA-riboside) gave 2-amino-N-(β-D-ribofuranosyl)malondiamide, which was cyclized by treatment with ethyl orthoformate to furnish 1-β-D-ribofuranosyl-5-hydroxyimidazole-4-carboxamide (bredinin), a potent immunosuppressive nucleoside antibiotic.

著者

福川 清史 周東 智 平野 孝夫 上田 享

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.4, pp.1644-1646, 1984-04-25 (Released:2008-03-31)

参考文献数

7

被引用文献数

4 10

---

A novel synthesis of bredinin by the conversion of AICA-riboside through a photo-degradation product is described.

著者

田中 博道 松田 彰 飯島 秀治 早川 弘之 宮坂 貞

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.6, pp.2164-2167, 1983-06-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

25 40

---

A new class of 5, 6-disubstituted uridines, in which the C-6 position was occupied by phenylthio group or iodine, were synthesized via lithiation of the corresponding 5-substituted 2', 3'-O-isopropylidene-5'-O-methoxymethyluridines and subsequent electrophilic reactions. These newly-synthesized uridine derivatives exhibited antileukemic activities against mouse leukemia L5178Y cells in culture.

著者

末宗 洋 林 教行 舟越 和久 秋田 弘幸 大石 武 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.33, no.5, pp.2168-2170, 1985-05-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

24 29

---

(S)-13-Hydroxy-9Z, 11E-octadecadienoic acid, a defensive substance in rice, was synthesized with high enantioselectivity by the reduction of the corresponding ketone with yeasts.

著者

甲斐 雅亮 三浦 哲朗 小橋 一弥 大倉 洋甫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.29, no.4, pp.1115-1120, 1981-04-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

31 32

---

A new fluorimetric method for the precise and rapid determination of guanidino compounds with benzoin is described. This is based on their reaction in an aqueous potassium hydroxide solution with benzoin (dissolved in methylcellosolve), in the presence of β-mercaptoethanol and sodium sulfite, while the pH of the reaction mixture is maintained at 9.2 after the reaction. This method requires heating at 100° for only 10 min. The excitation and emission maximum wavelengths of the fluorescence from these compounds are at around 325 and 435 nm, respectively. The method is simple, selective for guanidine and monosubstituted guanidino compounds (including peptides with one or two arginyl residues) and sensitive ; almost all the compounds can be determined at concentrations as low as 40-170 pmol/ml.

著者

Katsuhiko Sekimata Tomohiro Sato Naoki Sakai Hisami Watanabe Chiemi Mishima-Tsumagari Tomonori Taguri Takehisa Matsumoto Yoshifumi Fujii Noriko Handa Teruki Honma Akiko Tanaka Mikako Shirouzu Shigeyuki Yokoyama Kohei Miyazono Yoshinobu Hashizume Hiroo Koyama

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.67, no.3, pp.224-235, 2019-03-01 (Released:2019-03-01)

参考文献数

17

被引用文献数

11

---

Mutant activin receptor-like kinase-2 (ALK2) was reported to be closely associated with the pathogenesis of fibrodysplasia ossificans progressiva (FOP) and diffuse intrinsic pontine glioma (DIPG), and therefore presents an attractive target for therapeutic intervention. Through in silico virtual screenings and structure–activity relationship studies assisted by X-ray crystallographic analyses, a novel series of bis-heteroaryl pyrazole was identified as potent inhibitors of ALK2 (R206H). Derived from in silico hit compound RK-59638 (6a), compound 18p was identified as a potent inhibitor of ALK2 (R206H) with good aqueous solubility, liver microsomal stability, and oral bioavailability.

著者

宮下 修 松村 興一 島津 浩 橋本 直人

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.29, no.11, pp.3181-3190, 1981-11-25 (Released:2008-03-31)

参考文献数

36

被引用文献数

12 28

---

A series of 5-fluoro-6-substituted-5, 6-dihydrouracil-5-carboxylic esters (13), -5-carboxamides (15, 16), and -5-carbonitriles (18, 19) was prepared by direct fluorination of the corresponding uracil-5-carboxylic esters (6), -5-carboxamide (14), and -5-carbonitrile (17) with fluorine or trifluoromethyl hypofluorite (CF3OF) in the presence of water, methanol and/or acetic acid. Hydrolysis of the above-mentioned products under mild conditions gave 5-fluorouracil (1a) in high yield. Some applications of the present method for the synthesis of 1-(2-tetrahydrofuryl)-5-fluorouracil (1b) were also described.

著者

丸本 龍二 吉岡 義夫 古川 純康 本庄 美喜男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.24, no.11, pp.2624-2628, 1976-11-25 (Released:2008-03-31)

被引用文献数

8 9

---

Reaction of aristeromycin (I) with acetyl bromide in acetonitrile, followed by treatment with hydrobromic acid afforded 3'β-bromo-3'-deoxyaristeromycin hydrobromide (V) and 2'β-bromo-2'-deoxyaristeromycin hydrobromide (VI). Catalytic reduction of V and VI with palladium on charcoal gave 3'-deoxyaristeromycin (X) and 2'-deoxyaristeromycin (XI), respectively. Treatment of V with sodium alkoxide yielded 2', 3'-anhydroaristeromycin (IV). Two carbocyclic analogs (XII and XV) of inosine and 6-mercaptopurine ribonucleoside, 8-bromoaristeromycin (XVI) and 8-hydroxyaristeromycin (XVII) were also prepared.

著者

丸本 龍二 吉岡 義夫 宮下 修 島 俊介 今井 欣一 川添 勝義 本庄 美喜男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.23, no.4, pp.759-774, 1975-04-25 (Released:2008-03-31)

被引用文献数

23 40

---

A large scale preparation of 2-haloadenosines (1) was attained by acetylation of 2-haloinosines (3), followed by chlorination and amination. 2-Alkoxyadenosines (5) were prepared in fairly good yields by protection of both 2'- and 3'-hydroxyl groups of 2-chloroadenosine (1a) or 2-chloroinosine (3a), followed by substitution of the chlorine atom with alkoxy group. In the reaction of 1a with sodium alkoxide, there were obtained some oligomers of 5, of which the structures were elucidated. The reaction of 5-amino-4-cyano-1-β-D-ribofuranosylimidazole with carbon disulfide afforded 2, 6-di-mercapto-9-β-D-ribofuranosylpurine (15), which was converted to 2-mercaptoadenosine (14e) and its S-substituted derivatives. 2-Phenylaminoadenosine (29e) was prepared with comparative ease via 2-phenylamino-2', 3', 5'-tri-O-acetylinosine (32), the synthesis of which was effected by acetylation of 2-phenylaminoinosine (30) with acetylchloride in acetic acid. Many 2-substituted adenosines including O-substituted 2-hydroxyadenosines, S-substituted 2-mercaptoadenosines, N2-substituted 2-aminoadenosines, 2-alkyl- and -aryl-adenosines were prepared, among which several compounds were found to have a remarkable coronary vasodilating potency. Compound (29e) showed not only a strong potency, but also a longer duration of the effect than that of 1a. The structure-coronary vasodilating activity relationship was also discussed.

著者

丸本 龍二 本庄 美喜男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.22, no.1, pp.128-134, 1974-01-25 (Released:2008-03-31)

被引用文献数

31 41

---

The reaction of uridine with acyl bromide in acetonitrile (or ethyl acetate) afforded 3', 5'-di-O-acyl-2'-bromo-2'-deoxyuridine (II, V) in good yield, which was converted to 2'-deoxyuridine by hydrogenation and subsequent deacylation. A silmiar reaction of N4-acetylcytidine with acetyl bromide yielded 1-(2, 5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-N4-acetylcytosine (VIII), which was converted to 3'-deoxycytidine (X) by hydrogenation and subsequent deacylation with a concomitant formation of 2', 3'-dideoxycytidine (XII) and to 1-β-D-arabinofuranosyl cytosine (XI) by treatment with potassium hydroxide in ethanol. A similar reaction of cytidine with acyl bromide gave 2, 2'-anhydro-1-(3, 5-di-O-acyl-β-D-arabinofuranosyl) cytosine hydrobromide (XIV, XVI). These reaction mechanisms were also presented.

著者

上田 武雄 辻 忠和 百名 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.11, no.7, pp.912-917, 1963-07-25 (Released:2008-03-31)

被引用文献数

3 7

---

The replacement of 4-hydroxyl group of aminopyrimidinols by sulfhydryl in one step, through the action of phosphorus pentasulfide in triethylamine or 3-picoline. 5-Acylamino-6-amino-4-pyrimidinols were treated with phosphorus pentasulfide in pyridine, to yield thiazolo [5, 4-d] pyrimidine and 6-purinethiol compounds. The yield of both two type compounds were changed according to a functional group in the starting substance. These products, in addition, other 6-purinethiol and related compounds were screened as to their antiviral activities on poliomyelitis virus. Any of the compounds, however, did not exert a significant activity on the virus.

著者

桜井 邦好 青柳 栄 豊福 初則 大木 実 吉沢 豊吉 黒田 敏男

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.11, pp.3565-3566, 1978-11-25 (Released:2008-03-31)

被引用文献数

3 4

---

Selective N1-tetrahydrofurylation of uracils has been performed in satisfactory yield by direct addition of uracils to 2, 3-dihydrofuran in the presence of PCl5 in hexamethyl-phosphoramide (HMPA).

著者

野村 容朗 吉岡 義夫 南 功

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.4, pp.899-906, 1979-04-25 (Released:2008-03-31)

被引用文献数

7 13

---

Addition of 5-fluorouracil (1) to the double bond of 2, 3-dihydrofuran (3) without using any catalyst progressed smoothly at an elevated temperature and afforded an equilibrium mixture of 1-(tetrahydro-2-furyl)-5-fluorouracil (5) and 1, 3-bis (tetrahydro-2-furyl)-5-fluorouracil (7). By choosing favourable reaction conditions, each of these compounds was obtained in high yield. Thermal decomposition of 7 gave an equimolar mixture of 3 and 5. At a higher temperature, 5 underwent thermal reaction to yield 1 and 3. Study of the present addition reaction was extended to other 5-substituted uracils (8, R=-H, -CH3, -Cl, -Br, -COOCH3, -CONH2, -CN) which furnished the corresponding 1-(tetrahydro-2-furyl)-and 1, 3-bis (tetrahydro-2-furyl)-derivatives (9-15, 18-23) with high yields. A very small amount of 3-(tetrahydro-2-furyl)-5-substituted uracils (6, 16, 17) by-produced in the reactions was isolated and the structures unequivocally identified.

著者

丸中 照義 南 慶典 梅野 幸彦 安田 昭男 佐藤 俊幸 藤井 節郎

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.28, no.6, pp.1795-1803, 1980-06-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

7 6

---

Four metabolites of the antitumor agent 1-(tetrahydro-2-furanyl)-5-fluorouracil, formed in vitro by rat liver microsomes, were isolated by thin-layer chromatography or high-performance liquid chromatography. On the basis of mass spectrometry, 1H-NMR spectral analysis, and comparison with authentic samples, these metabolites were identified as 1-(trans-4-hydroxytetrahydro-2-furanyl)-5-fluorouracil, 1-(cis-4-hydroxytetrahydro-2-furanyl)-5-fluorouracil, 1-(trans-3-hydroxytetrahydro-2-furanyl)-5-fluorouracil and 1-(4, 5-dehydrotetrahydro-2-furanyl)-5-fluorouracil. These metabolites were also found in the plasma and urine of rats after administration of 1-(tetrahydro-2-furanyl)-5-fluorouracil.

著者

鴻巣 俊之 田島 和 武田 憲子 宮岡 武男 笠原 真由美 安田 紘 老田 貞男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.39, no.10, pp.2581-2589, 1991-10-25 (Released:2008-03-31)

参考文献数

7

被引用文献数

9 16

---

New triazole compounds were designed and synthesized as potential inhibitors of the fungal cytochrome P-450 14α-demethylase. In testing for antifungal activity against a mouse systemic Candida albicans infection, (2R, 3R)-3-acylamino-2-aroyl-2-butanol derivatives III exhibited remarkably high efficacy after oral or parenteral administration. The structure-activity relationships of these amidoalcohols were evaluated.

著者

相山 律男 永井 久子 沢田 誠吾 横倉 輝男 糸川 秀治 中西 守

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.10, pp.2810-2813, 1992-10-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

12 16

---

Self-association of irinotecan hydrochloride (CTP-11) in an aqueous solution was studied using UV, circular dichroism (CD), 1H-NMR and the quasi-elastic light scattering (QLS) method. The UV spectra showed a hypochromic effect in the aqueous solution. In the CD spectra, typically positive Davydov splitting was observed and the Δε value was reduced sigmoidally when the concentraion of CTP-11 was decreased. In the 1H-NMR, the aromatic signals of higher concentration shifted to a diamagnetic direction compared with those of lower concentration. These observations suggested that CPT-11 molecules are present as monomer in the lower concentration, and the self-association with positive helicity occurs by vertical stacking more than 10 μM of concentration. Its molecules form complete aggregates at more than 2 mM of the concentration. Results of QLS which coincided in the prediction of partition coefficient experiments suggested that CPT-11 molecules formed dimer under the condition. By the regression analysis of CD spectral data, the equilibrium constant for the self-association was calculated to be 2.41×10-4 M-1.

著者

山田 幸子 石川 正幸 金子 主税

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.23, no.11, pp.2818-2834, 1975-11-25 (Released:2008-03-31)

被引用文献数

12 22

---

Photolysis of a series of acridine 10-oxides (Ia-Ig) in various solvents is reported. The structures of photo-products were determined by syntheses, chemical transformation to the known compounds, or by direct examination of their spectroscopic data. Based on the structures of photo-products and the solvent effect on the product distribution in these photolyses, a mechanistic rationalization of these photo-reactions is presented. The characteristic features of the photo-rearrangement reactions of acridine 10-oxides are discussed and compared with those of bicyclic and monocyclic azine N-oxides, e, g., quinoline 1-oxides and pyridine 1-oxides.

著者

沢田 誠吾 宮坂 貞 荒川 基一

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.1, pp.275-287, 1978-01-25 (Released:2008-03-31)

被引用文献数

2 2

---

1-(Substituted-phenyl)-2, 3-tetramethylenepyrrolo [2, 1-b] benzothiazoles (IV-2-IV-17) were synthesized from the correspoding 3-(substituted-phenyl) thiazolo [2, 3-b] benzothiazolium perchlorates (III) by the reaction of 1-morpholino-1-cyclohexene, an enamine. On reaction with cuprous cyanide p-substituted bromobenzene (IV-2) furnished benzonitrile (IV-23), which was converted into the corresponding 1-phenyl derivatives (IV) with various aliphatic functional groups at the para position of the phenyl moiety. On reaction with methylmagnesium iodide and subsequent acid hydrolysis IV-23 was converted into acetophenone (IV-24), which reacted with methyltriphenylphosphylene to give 2-phenylpropylene (IV-38). Hydroboration of IV-38 afforded 2-phenylpropanol (IV-39), which was oxidized into the corresponding propionic acid (IV-43), the sulfur atom being oxidized at the same time into sulfoxide. Deoxygenation of the ester (IV-44) was successfully carried out with PBr3 to obtain the desired α-phenyl substituted propionic acid ester (IV-45).