著者

増田 克忠 神谷 高明 今城 芳夫 金児 龍彦

出版者

公益社団法人日本薬学会

雑誌

CHEMICAL & PHARMACEUTICAL BULLETIN (ISSN:00092363)

巻号頁・発行日

vol.19, no.1, pp.72-79, 1971

被引用文献数

25

---

A number of N-acyl and N-nitroso-3-dialkylaminosydnonimines (II) were synthesized by various acylating methods. In some cases, the acylation with activated esters, mixed anhydrides or dicyclohexylcarbodiimide was found to be more favorable. The reactivities of these derivatives towards acids and alkalis were investigated. Trifluoroacetyl (II-6) and formyl (II-1) compounds were easily deacylated in varuous conditions. Methylation took place at the acylated imino nitrogen of N-ethoxycarbonyl compound to give the quaternary salt (II-18). N-Acetyl compound (II-2) was compared with its 3-alkyl analog in the physicochemical properties ; its pK<SUB>a</SUB> values reveals that the morpholino group has little effect on the basicity of the compound.

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

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

白石 忠義 亀山 啓司 今井 直博 堂本 剛史 勝見 郁男 渡辺 清

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.36, no.3, pp.974-981, 1988

被引用文献数

23

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A series of α-cyanocinnamamide derivatives was synthesized and evaluated for inhibitory activity against tyrosine-specific protein kinase using intact plasma membrane fractions from an epidermoid carcinoma cell line, A-431 cells. Among these compounds, several novel α-cyano-4-hydroxy-3, 5-disubstituted cinnamamide derivatives, e.g., α-cyano-3-ethoxy-4-gtdrixt-5-phenyl-thiomethylcinnamamide (ST 638), showed potent inhibitory activity. The studies on the structure-activity relationship revealed that the presence of the hydroxy group at the 4 position and the double bond in the α-cyano-4-hydroxycinnamamide skeleton was important for potent inhibitory activity, and that the presence of hydrophobic groups at the 3 and 5 positions on the benzene ring also enhanced the inhibitory activity of α-cyano-4-hydroxycinnamamide derivatives.

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

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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

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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.

著者

早川 弘之 高井 富美 田中 博道 宮坂 貞 山口 健太郎

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.5, pp.1136-1139, 1990-05-25 (Released:2008-03-31)

参考文献数

18

被引用文献数

18 23

---

Displacement of a hydroxyl group in pyrimidine nucleosides having a vicinal diol system by a fluorine atom was investigated by using diethylaminosulfur trifluoride (DAST). Though participation of the base moiety often thwarts the desired introduction of a fluorine atom, it was found that appropriate modification of the base and/or sugar moieties allowed the desired fluorodehydroxylation to occur, giving 5'-, 3'-β-, and 2'-α-fluorinated uracilnucleosides in good yields.

著者

亀田 幸雄 大平 貞夫 松井 勝彦 金友 昭一 長谷 哲 阿津坂 巧

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.4, pp.938-944, 1974-04-25 (Released:2008-03-31)

被引用文献数

78 111

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For the purpose of finding out a strain which has stronger cytolytic activity on Ehrlich ascites carcinoma cells, the authors isolated 113 strains of Bacillus natto from straws, which were collected at various areas in Japan, and measured the cytolytic activities by cylinder plate method. As the results, the authors found out a strain of Bacillus natto (tentatively called KMD 2311) which has the strongest cytolytic activity in the 113 strains. There were at least two kind of cytolytic substances on Ehrlich ascites carcinoma cells in the culture medium of Bacillus natto KMD 2311. One was extracted with AcOEt from the culture medium, which constitute approximately 20% of the cytolytic activity in the culture medium and it was stable. This cytolytic substance was purified and colorless crystalline compound (mp 247-249°) was obtained by recrystallization from acetone-petr. ether. Chemical structure of this compound was examined by elementary analysis, infrared, nuclear magnetic resonance, and mass spectroscopy and study of decomposed products. As the results, this compound was proved to be identical with surfactin (mp 140°), which was obtained from culture medium of Bacillus subtilis by Kakinuma, et al. and from Bacillus natto KMD 1126 by the authors. Melting point of this compound (mp 249°) was higher about 100° than that of surfactin (mp 140°), but high mp compound was obtained from surfactin by recrystallization from acetone-petr. ether. From these results, it was indicated that the cytolytic substance was identified with surfactin and dimorphic.

著者

HIDEO INOUE TOHRU UEDA

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.1743-1744, 1971-08-25 (Released:2011-02-08)

参考文献数

10

被引用文献数

12 17

著者

井上 英夫 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.26, no.9, pp.2664-2667, 1978-09-25 (Released:2008-03-31)

被引用文献数

3 7

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Treatment of 5'-acetylthio-5'-deoxy-2', 3'-O-isopropylidene-5-bromouridine, prepared from 2', 3'-O-isopropylidene-5-bromouridine, with sodium methoxide in methanol afforded 5'-deoxy-5'-thio-2', 3'-O-isopropylidene-S6, 5'-cyclouridine. Deacetonation of the product gave 5'-deoxy-5'-thio-S6, 5'-cyclouridine, a sulfur-bridged cyclouridine fixed in the"anti"conformation. Starting from the 5'-amino derivative a N6, 5'-cyclouridine was similarly prepared. The nuclear magnetic resonance and mass spectra of a series of O-, N- and S-cyclouridines were compared and the characteristic features were discussed.

著者

YUKARI SUZUKI AKIRA MATSUDA TOHRU UEDA

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.1808-1811, 1987-05-25 (Released:2009-10-19)

参考文献数

7

被引用文献数

10 10

---

Oxidation of 6, 5'-cyclo-5'-deoxy-2', 3'-Ο-isopropylideneuridine with selenium dioxide gave the 5'-oxo derivative, which was converted to the 5'-ethoxycarbonylmethylidene derivative (3). Reduction of 3 afforded, after deprotection, the title compounds (6, R and S). The base-catalyzed epimerization of 6 at the 5'-position was observed, and the equilibrium was in favor of the (R) -epimer.

著者

吉村 祐一 / 上田 享 松田 彰 Akira MATSUDA

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.7, pp.1761-1769, 1992-07-25 (Released:2008-03-31)

参考文献数

49

被引用文献数

20 28

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6, 1'-Propanouridine (10), a carbon-bridged cyclouridine fixed in the syn-conformation, was synthesized from D-fructose. Two additional carbon-units were introduced at the 1'-position of 1'-hydroxymethyl-O2, 2'-anhydrouridine 13 and inversion of the 2' hydroxyl group was achieved by sequential oxidation-reduction reactions. Finally, the spiro-carbon bridge was constructed by radical cyclization of the 1'-iodopropyl derivative of 5-chlorouridine. Dehydrochlorination followed by deprotection gave the desired 10. The circular dichroism (CD) spectrum of 10 showed a negative Cotton effect ([θ]=-6100) at the main absorption region, whereas 5'-O-tert-butyldimethylsilyl-2', 3'-O-isopropylidene-6, 1'-propanouridine (30) showed almost no Cotton band at the same absorption region. These results suggest that the critical region in which the CD Cotton effect changes from negative to positive is present in the syn region where 10 is located. Correlation of the magnitude and the direction of the sign of the CD Cotton effect and the torsion angle (χ) is also discussed.