著者

ZHUO-FENG XIE YUKINOBU ICHIKAWA HIROSHI SUEMUNE KIYOSHI SAKAI

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.5, pp.1812-1816, 1987-05-25 (Released:2009-10-19)

参考文献数

9

被引用文献数

4 7

---

The conversion of (+) -limonen-10-ol (7) into the key intermediate for the synthesis of carbacyclin (1), (+) - (1S, 2R, 3R, 5R) -3-acetoxy-2-methoxycarbony1-7-oxobicyclo [3.3.0] octane (2), is described. The cis-3, 4-disubstituted cyclopentanone prepared from 7 via a sequence of reactions involving Rh (I) -catalyzed cyclization could be converted to the 3-acetylbicyclo [3.3.0] oct-2-ene skeleton, which was subjected to 1, 4-addition reaction with CN-. The resulting cyano compound was transformed into the key intermediate 2 through appropriate modification of the substituents on the five-membered ring. This synthetic method provides a new route to carbacyclin.

著者

飯森 隆昌 村井 安 脇坂 康尋 大塚 晏央 大内 章吉 児玉 佳男 大石 武

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.41, no.4, pp.775-777, 1993-04-15 (Released:2008-03-31)

参考文献数

14

被引用文献数

2 8

---

Conformational restrictions of sangivamycin (1) could be achieved by the use of the gauche effect of the substitutents on the ribofranose moiety. The conformational deviations obtained by this method were found to nicely correlate with the inhibitory activity of PKC.

著者

池原 森男 伊村 純子

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.3281-3285, 1981-11-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

11 17

---

The reaction of N2-isobutyryl-9-(2'-O-trifluoromethanesulfonyl-3', 5'-di-O-tetrahydrofuranyl-β-D-arabinofuranosyl) guanine with tetra-n-butylammonium fluoride or an appropriate metal halide in dimethylformamide aftorded N2-isobutyryl-3', 5'-di-O-tetrahydrofuranyl-2'-halogeno-2'-deoxyguanosines. The deprotection of these products led to 2'-halogeno-2'-deoxyguanosines. The ultraviolet absorption properties, 1H and 13C nuclear magnetic resonance spectral properties of the products were recorded.

著者

上杉 晴一 三木 弘子 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.29, no.8, pp.2199-2204, 1981-08-25 (Released:2008-03-31)

参考文献数

41

被引用文献数

3 7

---

^<13>C nuclear magnetic resonance spectra of various 2'-substituted 2'-deoxyadenosines are presented. The relative substituent chemical shifts of each sugar carbon are analyzed in terms of a substituent electronegativity parameter and compared with the data for substituted cyclohexanes. The relative substituent chemical shifts of C2' and C4' are controlled mainly by the inductive effect of the substituent. Those of C1' and C3' cannot be interpreted by inductive effect only. Some effect which is perturbed by the presence of a cis-substituent seems to be operating. A good linear correlation was observed between the substituent chemical shift of C2' and the N conformer population in the furanose puckering equilibrium.

著者

池原 森男 伊村 純子

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.1034-1038, 1981-04-25 (Released:2008-03-31)

参考文献数

18

被引用文献数

15 16

---

2'-Deoxy-2'-fluoroguanosine (VII) was synthesized starting from 8, 2'-anhydro-8-oxy-9-β-D-arabinofuranosylguanine (8, 2'-O-cycloguanosine) (I). Compound I was protected at 2-NH2 with an isobutyryl group and at 3'- and 5'-OH with tetrahydrofuranyl groups. The protected compound III was derivatized to the arabino nucleoside V and thence converted to VII by treatment with trifluoromethanesulfonyl chloride and tetra-n-butylammonium fluoride. The resulting 2'-deoxy-2'-fluoroguanosine showed a 3'-endo favored conformation.

著者

/ 岩本 真承 青木 俊二 田中 直美 田嶋 清子 山原 條二 高石 喜久 吉田 雅昭 富松 利明 玉井 洋進 Yoshin TAMAI

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.2, pp.397-399, 1991-02-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

40 73

---

It has been reported that an acetone extract of ginger and its fractions have anti-5-HT (5-hydroxytryptamine; serotonin) effects. In the present study, guinea pig ileum, rat stomach fundus and rabbit aortic strips are used in order to determined the constituents of fraction 2 which are responsible for anti-5-HT effect and to examine their pharmacological properties.The analysis of fraction 2-3 indicated that galanolactone, a diterpenoid, is one of the active constituents. In guinea pig ileum, galanolactone inhibited contractile responses to 5-HT with a pIC50 value 4.93. pIC50 value of galanolactone against the response to 2-methyl-5-HT, a selective 5-HT3 agonist, in the presence of methysergide at 1×10-5M was 5.10. pIC50 values of ICS 205-930, a selective 5-HT3 antagonist, were 5.30 and 7.49, respectively. The concentration-response curve of 5-HT was shown as a biphasic curve and galanolactone caused a selective shift to the right of the second phase.In the same preparations, the pIC50 value of galanolactone and ICS 205-930 against the response to carbamylcholine (CCh) was 4.45 and 4.46.The inhibitory effect of galanolactone on the 5-HT response in the stomach fundus and aortic strips was less than that in the ileum.In addition, in the thoracic aorta precontracted with 50 mM K+, the relaxing effect of galanolactone was about 1/10 of that of papaverine.These results suggest that the anti-5-HT effect of galanolactone, a diterpenoid isolated from ginger, is related to antagonism of 5-HT3 receptors.

著者

末宗 洋 田中 正一 尾葉石 浩 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.1, pp.15-21, 1988-01-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

9 18

---

Synthesis of prostaglandin A2 (PGA2) by means of a route involving enzymatic reactions is described. Enantioselective reduction and hydrolysis of trans-3, 4-bis(methoxycarbonyl)cyclopentanone (1) were examined using yeasts or enzymes, and it was found that (+)- and (-)-1 are easily obtained by an enzymatic procedure. Compound (+)-1 was converted to the Corey intermediate for PGA2 via the regioselective hydrolysis of the (+)-diacetate (8) with porcine pancreatic lipase. This synthesis based on the enzymatic approach was proved to be useful for the synthesis of both PGA and PGE from (-)-1.

著者

Masayo SAKATA Takanori SUEDA Hirotaka IHARA Chuichi HIRAYAMA

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.44, no.2, pp.328-332, 1996-02-15 (Released:2008-03-31)

参考文献数

16

被引用文献数

2 3

---

Novel copolymeric adsorbents for the selective removal of endotoxin from an acidic protein solution were prepared. The adsorbents comprise spherical copolymers derived from N, N-dimethylaminopropylacrylamide (DMAPAA) and divinylbenzene (DVB). When the molar ratio of DMAPAA to DVB was 80/20 (amino-group content : 5.1 meq/g) and the pore size (molecular mass exclusion of polysaccharide, Mlim) was 4000 to 10000, DMAPAA/DVB showed high endotoxin-adsorbing activity at pH 5.0 to 9.0 and ionic strengths of μ=0.05 to 0.4. The capacity of the adsorbent (Mlim : 4000) was 390 μg of endotoxin (lipopolysaccharide purified from E. coli O111 : B4) per ml of the adsorbent using the batchwise method. The apparent dissociation constant between endotoxin and the adsorbent was 2.2×10-12 M. On the other hand, the adsorption of bovine serum albumin, an acidic protein, by the adsorbent increased with an increase in Mlim from 4000 to 10000, but decreased with an increase in ionic strength (μ) from 0.05 to 0.2 As a result, DMAPAA/DVB (80/20)(Mlim : 4000)selectively removed endotoxin from various acidic protein solutions at pH 7.0 and μ=0.05. The residual concentration of endotoxin in the protein solution always decreased to a concentration lower than 0.1 ng/ml, and recovery of the protein was more than 97%.

著者

坂田 眞砂代 河合 透 大隈 邦夫 伊原 博隆 平山 忠一

出版者

The Pharmaceutical Society of Japan

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.16, no.11, pp.1065-1068, 1993-11-15 (Released:2008-04-10)

参考文献数

23

被引用文献数

11 12

---

We describe a method for the removal of endotoxins from various crude antigen solutions originating from gram-negative bacteria using aminated poly(γ-methyl L-glutamate) (PMLG) spherical particles. The aminated PMLG adsorbents showed high affinity for various purified endotoxins at an ionic strength of μ=0.1. The endotoxin-adsorbing capacity of the adsorbent increased with increase in the amino-group content of the adsorbent. The adsorbent (3.2 meq/g amino-group content) showed the highest affinity for endotoxin at ionic strengths ranging from μ=0.025-0.8. The adsorption of Bordetella pertussis antigen to the adsorbent decreased with increasing amino-group content of the adsorbent at an ionic strength of μ=0.2. The adsorption of B. bronchiseptica protein to the adsorbent increased with increasing amino-group content of the adsorbent, but decreased with increasing ionic strength. The adsorbent (3.2 meq/g of amino-group content) selectively reduced endotoxin in crude antigen solutions originating from gram-negative bacteria, B. pertussis, B. bronchiseptica and Pasteurella multocida, even at a high ionic strength (μ=0.2-0.4) without affecting the recovery of the protective antigens.

著者

平山 忠一 坂田 眞砂代 大倉 幸洋 伊原 博隆 大隈 邦夫

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.8, pp.2106-2109, 1992-08-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

10 10

---

Attempts were made to prepare adsorbents having a high affinity for endotoxin in the culture supernatant of Bordetella pertussis. When poly(γ-methyl L-glutamate) (PMLG) was used as a matrix and amino groups as the ligand, the highest affinity for endotoxin was attained even at a high ionic strength (μ=0.2-0.4). PMLG beads containing amino groups of about 3.2 meq/g selectively removed endotoxin from the culture supernatant of B. pertussis without affecting the protective antigens. It was demonstrated that 1 ml of the wet adsorbent adsorbed 4.5 mg of endotoxin. The beads of PMLG derivatives, therefore, are considered to be a useful adsorbent for the removal of endotoxin from the pertussis vaccine, affecting neither filamentous hemagglutinin nor pertussis toxin.

著者

原田平 輝志 前田 稔 金沢 洋子 桃園 裕子 小嶋 正治

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.3, pp.1407-1410, 1986-03-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

6 7

---

Interconversion of 2-deoxy-2-fluoro-D-glucose (FDG) and 2-deoxy-2-2-fluoro-D-mannose (FDM) catalyzed by acid has been detected by 19F-NMR method. Although FDG and FDM were stable towards 1 N hydrochloric acid, in stronger acidic media the two hexoses underwent epimerization at C-2.

著者

小嶋 正治 栗原 悟 金沢 洋子 原田平 輝志 前原 喜彦 遠藤 英也

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.1194-1197, 1988-03-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

8 11

---

The metabolic products of 2-deoxy-2-fluoro-D-glucose (FDG) and 2-deoxy-2-fluoro-D-mannose (FDM) in sarcoma 180 cells transplanted in mice were investigated by fluorin-19 nuclear magnetic resonance (19F-NMR) spectroscopy. It became apparent that the administered FDG was converted to FDM (and/or FDM-6-phosphate) in tumor cells, and also the administered FDM was converted to FDG (and/or FDG-6-phosphate). At 9h after administration of FDM, the ratio of FDG (and/or FDG-6-phosphate) and FDM (and/or FDM-6-phosphate) reached equilibrium. On the other hand, it took more than 48h in the case of FDG administration. The equilibrium amount of FDM (and/or FDM-6-phosphate) was approximately four times as much as that of FDG (and/or FDG-6-phosphate) in both cases.

著者

Yoko Kanazawa Yuko Momozono Hideki Yamane Terushi Haradahira Minoru Maeda Masaharu Kojimaa

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.2, pp.895-897, 1987-02-25 (Released:2009-10-19)

参考文献数

5

被引用文献数

8 8

---

2-Deoxy-2-fluoro-D-glucose (FDG) or its 6-phosphate (FDG-6-P) was detected by19F NMR in the organs and urine of mice previously injected with 2-deoxy-2-fluoro-D-mannose (FDM). This conversion of FDG (-6-P) to FDM (-6-P) in vivo was reversible.

著者

原田平 輝志 前田 稔 甲斐 康信 尾前 裕子 小嶋 正治

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.1, pp.165-172, 1985-01-25 (Released:2008-03-31)

参考文献数

22

被引用文献数

26 34

---

Methyl 3-O-benzyl-4, 6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-mannopyranoside (7) was examined as a substrate for the preparation of 2-deoxy-2-fluoro-D-glucose (1) by fluoride ion treatment. The triflate (7) reacted rapidly with tetraalkylammonium fluorides in acetonitrile or tetrahydrofuran to give methyl 3-O-benzyl-4, 6-O-benzylidene-2-deoxy-2-fluoro-β-D-glucopyranoside (10) in 52-57% yield. Removal of the protecting groups from 10 by the use of 50% methanesulfonic acid afforded the required 1 in good yield. This synthetic sequence may provide an effective alternative to known methods for preparing 18F-labeled 1.

著者

原田平 輝志 前田 稔 矢野 裕二 小嶋 正治

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.8, pp.3317-3319, 1984-08-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

15 18

---

A nucleophilic displacement reaction of methyl 3, 4-O-isopropylidene-2-O-(trifluoromethanesulfonyl)-6-O-trityl-β-D-talopyranoside (10) with tetraalkylammonium fluorides in acetonitrile gave methyl 2-deoxy-2-fluoro-3, 4-O-isopropylidene-6-O-trityl-β-D-galactopyranoside (11). Excellent conversion of 11 into 2-deoxy-2-fluoro-D-galactose (1) was achieved by hydrolysis with 5 N hydrochloric acid.

著者

菊川 清見 佐藤 史子 鶴尾 隆 井村 伸正 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.16, no.6, pp.1110-1115, 1968-06-25 (Released:2008-03-31)

被引用文献数

13 23

---

2'-O-Benzyl-4-methylthiouridine (III) and 2'-O-benzylcytidine (VI) were obtained by respective treatment of 4-methylthiouridine (II) and cytidine (V) with benzyl bromide in the presence of sodium hydride. By this reaction, highly specific benzylation of 2'-hydroxyl group of the ribonucleosides was achieved. The both compounds (III) and (VI) could easily be converted to 2'-O-benzyluridine (IV) which is an important intermediate in the synthesis of oligonucleotide.

著者

井村 伸正 鶴尾 隆 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.16, no.6, pp.1105-1109, 1968-06-25 (Released:2008-03-31)

被引用文献数

9 18

---

Uridine was benzylated with benzyl bromide in the presence of sodium hydride in dimethyl sulfoxide or dimethylformamide to give two products. The one was a dibenzyl uridine (I), yield 33%, and the other N3-benzyluridine (II), yield 30.5%. The product (I) was converted to the product (II) by catalytic hydrogenation and was identified with N3, 2'-O-dibenzyluridine which was synthesized by detritylation of N3, 2'-O-dibenzyl-3', 5'-di-O-trityluridine (IV) derived by the similar benzylation of the known 3', 5'-di-O-trityluridine (III).

著者

大塚 栄子 若林 利明 田中 正治 田中 俊樹 押柄 和幸 長谷川 明 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.29, no.2, pp.318-324, 1981-02-25 (Released:2008-03-31)

参考文献数

25

被引用文献数

7 14

---

2'-and 3'-O-(o-Nitrobenzyl) derivatives of uridine, cytidine, adenosine and guanosine were synthesized by treatment of uridine, N-benzoylcytidine, N-benzoyladenosine and N-isobutyrylguanosine, respectively, with o-nitrophenyldiazomethane followed by isolation and deblocking. 3'-O-(o-Nitrobenzyl) guanosine is a novel compound. By using N-acylated nucleosides, separation of the 2'-and 3'-substituted isomers on silica gel became feasible and these compounds were useful intermediates for the synthesis of oligoribonucleotides. Some physical properties of these compounds were studied by ultraviolet, nuclear magnetic resonance, circular dichroism and the 2'-substituted isomers were found to have more stacked structures than the 3'-isomers.

著者

大塚 栄子 田中 正治 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.5, pp.949-959, 1977-05-25 (Released:2008-03-31)

被引用文献数

25 36

---

Previously 2'-O-(o-nitrobenzyl) uridine was synthesized via 2', 3'-O-(stannylene) uridine and used in the synthesis of UpA and UpU. 2'-O-(o-Nitrobenzyl) derivatives of cytidine and adenosine were synthesized with o-nitrobenzyl bromide in the presence of sodium hydride. 3'-O-(o-Nitrobenzyl) cytidine was also isolated. Using these 2'-protected nucleosides, partially protected trinucleoside diphosphates, CpA (o-nitrobenzyl)-pA and CpCpA (o-nitrobenzyl) were synthesized using a diester method or a triester method. These oligomers are candidates as suitable substrates of ribonucleic acid (RNA) ligase. Removal of the o-nitrobenzyl group was effected by irradiation with ultraviolet spectrum (UV) light (wavelength longer than 280 nm) and the completely deblocked oligonucleotides were characterized by enzymatic hydrolysis.

著者

福川 清史 上田 亨 平野 孝夫

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.5, pp.1582-1592, 1983-05-25 (Released:2008-03-31)

参考文献数

41

被引用文献数

18 26

---

Neplanocin A (1) and N6-benzoylneplanocin A (2) were converted to the corresponding 3', 6'-O-(tetraisopropyldisiloxane-1, 3-diyl)-neplanocin A's (3, 4). The 2'-hydroxy group in 3 and 4 was triflated (5, 6). Nucleophilic displacement of 5 and 6 with a number of nucleophiles (I-, Br-, Cl-, N3-, AcO-, AcS-) in hexamethylphosphoric triamide afforded the corresponding 2' (R)-substituted derivatives in high yields. The 2' (S)-azido derivatives were obtained in a similar manner from arabinoneplanocin A prepared by this method. Adenosine was also converted to 2' (R)-substituted derivatives, including arabinofuranosyladenine, as well as 2' (S)-substituted adenosines. The physical properties of these 2'-substituted derivatives of neplanocin A and adenosine, including nuclear magnetic resonance and circular dichroism spectra, are presented.