著者

今沢 正興 上田 亨 浮田 忠之進

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.3, pp.604-610, 1975-03-25 (Released:2008-03-31)

被引用文献数

19 30

---

New thiosugar nucleosides, 2'-deoxy-2'-mercaptouridine (III), its disulfide (IV), 2'-deoxy-2'-mercapto-3', 5'-di-O-acetyluridine (V), and 2'-deoxy-2'-methyl-thiouridine (VI) have been synthesized. The present synthetic method involves the use of 2'-deoxy-2'-acetylthio-3', 5'-di-O-acetyluridine (II) as the intermediate which was obtained by the reaction of 2, 2'-cyclo-3', 5'-di-O-acetyluridine (I) with thioacetic acid. The proton magnetic resonance (PMR) data of these compounds suggested that the introduction of sulfuratom at 2'-position resulted in the furanose ring puckering that is extremely biased to C2' endo-mode. 2'-Deoxy-2', 6-epithio-5, 6-dihydro-arabinofuranosyluracil (VIIIb), the 2'-epimer of III in an 2', 6-epithio form, was also synthesized.

著者

関谷 剛男 浮田 忠之進

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.15, no.10, pp.1503-1507, 1967-10-25 (Released:2008-03-31)

被引用文献数

1 2

---

A complex neighboring approach provided a successful synthesis of 2'-deoxy-2'-thio-3'-deoxy-3'-aminouridine (IX). 1-(3'-Deoxy-3'-amino-β-D-arabinofuranosyl) uracil (I) afforded, in three steps, the blocked dithiocarbamoyl mesylate (IV), which, on heating in pyridine, cyclized to the thiazoline (V), that was deblocked to VI and reduced to the thiazolidine (VII). Compound (VII) was successively treated with mercuric chloride and hydrogen sulfide to furnish the desired product (IX).

著者

金子 正勝 清水 文治

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.20, no.5, pp.1050-1053, 1972-05-25 (Released:2008-03-31)

被引用文献数

3 7

著者

AKIHIRO YAMAZAKI TERUO FURUKAWA MASAO AKIYAMA MASARU OKUTSU IZUMI KUMASHIRO MORIO IKEHARA

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.21, no.4, pp.692-696, 1973-04-25 (Released:2011-02-08)

参考文献数

17

被引用文献数

3 7

---

As the analog of thioinosine, 2-methyl-, 2-ethyl-, 2-methylthio-, and 2-methyiamino-6-mercapto-9-β-D-ribofuranosylpurine were synthesized. From thio-AICA-riboside, 5-formamido-1-(2', 3', 5'-tri-O-formyl-β-D-ribofuranosyl)-4-imidazolethiocarboxamide and 5-acetamido-1-(2', 3', 5'-tri-O-acetyl-β-D-ribofuranosyl)-4-imidazolethiocarboxamide were also prepared.

著者

池原 森男 宇野 準

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.2, pp.221-223, 1965-02-25 (Released:2008-03-31)

被引用文献数

6 9

著者

池原 森男 宇野 準 石川 文義

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.12, no.3, pp.267-271, 1964-03-25 (Released:2008-03-31)

被引用文献数

6 10

---

2', 3'-O-Isopropylidene-5'-O-benzoylinosine and 2', 3', 5'-tri-O-benzoylinosine were reacted with N, N-dimethylformamide-thionyl chloride complex in chloroform solution. Resulting 6-chloro compound was further reacted with morpholine, dimethylamine and thiourea to afford 6-morpholino-, 6-dimethylamino-and 6-mercapto-derivative of 9-β-D-ribofuranosylpurine in a good overall yield.

著者

MITSUAKI MAEDA MINEO SANEYOSHI YUTAKA KAWAZOE

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.19, no.8, pp.1641-1649, 1971-08-25 (Released:2011-02-08)

参考文献数

28

被引用文献数

14 19

---

The reaction mechanism for the hydrogen exchange of C-8 hydrogens of purine ribosides was discussed on the basis of the pD-rate profiles and the effect of 6-substituents on the rate. It was shown that the rate depended on concentrations of the purine and D2O and that the observed second-order rate constant was expressed as kOD-KD2O/Ka (N7) where kOD-was the rate constant for hydrogen exchange of N7-protonated purines by attack with the OD-, KD2O was the dissociation constant of D2O, and Ka (N7) was the dissociation constant of N7-protonated purines.

著者

池原 森男 林 元吉 福井 寿一

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.10, pp.2702-2707, 1977-10-25 (Released:2008-03-31)

被引用文献数

10 9

---

8-Methyladenosine (X) was synthesized by two ways starting from 2', 3'-O-isopropylidene-2-methylthioinosine (I). The compound (I) was methylated with t-butyl hydroperoxide in acidic media in the presence of ferrous ion to give 8-methyl compound (II) in a yield of 46%. Raney nickel dethiolation of II and acetylation at 5'-OH followed by chlorination using SOCl2/DMF gave 6-chloro-8-methylpurine derivative (V). The compound (V) was treated with liq. NH3 and deprotected with trifluoroacetic acid to give 8-methyladenosine (X). Alternatively II was acetylated at 5'-OH, chlorinated with Vilsmeyer-Haack reagent and treated with liq. NH3 to give 2', 3'-O-isopropylidene-2-methylthio-8-methyladenosine (IX). The compound (IX) was deacetonized and dethiolated with Raney nickel to give X. The physical properties of X was elucidated by ultraviolet, circular dichroism and nuclear magnetic resonance spectra. A syn type conformation was assigned to 8-methyladenosine.

著者

末宗 洋 明石 アイリ 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.3, pp.1055-1061, 1985-03-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

4 7

---

Chemical synthesis of platelet-activating factor (PAF, 1) and its enantiomer was studied. Several alkoxymethyl alkenyl ketones (5a-c, n=14 or 16) were synthesized from Wittig-Horner reagents (4, n=14 or 16) with cyclohexanecarboxaldehyde, octylaldehyde, and benzaldehyde, and subjected to asymmetric reduction with BINAL-H1) which is known to show high enantioselectivity in the reduction of enones. Optical purities of the reduction products (6) were determined from the 400 MHz proton nuclear magnetic resonance spectra after conversion of 6 to the esters (9) of optically active α-methoxy-α-trifluoromethyl-phenylacetic acid (MTPA). The MTPA ester of (+)-6b showed high optical purity (80%ee). Upon oxidative cleavage of the double bond with ozone followed by reduction with NaBH4, the acetate of (+)-6b afforded two known compounds (11 and 12), which have previously been transformed into natural PAF (1).

著者

末宗 洋 肥塚 美千代 鎌下 知子 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.1379-1381, 1989-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

15 21

---

γ-Hydroxyethyl α, β-unsaturated γ-lactone (2) is a promising intermediate for the synthesis of eldanolide and cis, cis-1, 2, 3-trisubstituted cyclopentane, which could be converted to 11-deoxyprostaglandins. In order to prepare optically active 2, enzymatic hydrolysis of (±)-trans-cyclohexene-4, 5-diacetate with Pseudomonas fluorescens lipase was examined, and the monoalcohol ((-)-6, >99%ee)with R-configuration was obtained in accored with prediction based on the three-site model proposed by us. Compound (-)-6 could be converted to the chiral lactone ((-)-2) via a sequence of reactions involving ring cleavage.

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

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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.