著者

梅澤 勲 野澤 雅子 南雲 紳史 秋田 弘幸

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.43, no.7, pp.1111-1118, 1995

被引用文献数

5

---

Three kinds of oudemansin X, (-)-1, (+)-1 and (±)-1, were totally synthesized. The key point in the present chiral synthesis was the enantioselective acetylation of the racemic alcohols, (±)-5 and (±)-8, using lipase in an organic solvent. The synthetic (-)-1 was found to exhibit strong antifungal activity against several molds and yeasts.

著者

今井 欣一 丸本 龍二 小林 邦夫 吉岡 義夫 戸田 準 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.19, no.3, pp.576-586, 1971-03-25 (Released:2008-03-31)

被引用文献数

11 19

---

Ring closure of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) with phenyl isothiocyanate afforded 2-mercaptoinosine (I) in good yield. Similarly, the ring closure of AICA-riboside 5'-phosphate (AICAR) led to the formation of 2-mercaptoinosine 5'-phosphate (II). Various 2-substituted inosine 5'-phosphates were prepared from I and II or starting with AICA-riboside. It was found that 2-furfuryl-thioinosine 5'-phosphate possessed a flavor enhancing activity of about 17-times that of inosine 5'-phosphate. The chemical structure-flavor enhancing activity relationship was presented.

著者

松田 彰 野本 裕二 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.27, no.1, pp.183-192, 1979-01-25 (Released:2008-03-31)

被引用文献数

16 31

---

A facile displacement of a methylsulfonyl group in adenosines with cyanide ion is described. Treatment of protected 8-methylsulfonyladenosines with sodium cyanide in dimethylformamide gave the 8-cyanoadenosines. The conversion of the cyano group to the methyl imidate, methoxycarbonyl, carbamoyl, and carboxylic acid, respectively, was achieved. Similar reaction was carried out with 2-methylsulfonyladenosines to give the 2-cyanoadenosines and their derivatives. The nuclear magnetic resonance (NMR) and circular dichroism (CD) spectra of these 2-and 8-substituted adenosines are given. The 8-substituted adenosines possess syn-conformations while the 2-substituted derivatives prefer to possess anti-conformations, as confirmed by the CD and NMR spectra.

著者

松田 彰 篠崎 操 宮坂 貞 町田 治彦 畔蒜 藤一

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.4, pp.1766-1769, 1985-04-25 (Released:2008-03-31)

参考文献数

24

被引用文献数

19 30

---

Reaction of 2-iodoadenosine (2) with terminal alkynes in the presence of bis (triphenylphosphine) palladium dichloride and cuprous iodide in triethylamine and N, N, -dimethylformamide gave 2-alkynyl-adenosines (3a-h) in excellent yields. Several compounds showed high activity as inhibitors in rat passive cutaneous anaphylaxis (PCA) reaction. Among them, 2-(3-hydroxypropynyl)- and 2-(3-hydroxybutynyl)-adenosines (3d, f) are much more potent than disodium cromoglycate (DSCG).

著者

松田 彰 佐藤 和恵 宮坂 貞 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.32, no.5, pp.2048-2051, 1984-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

4 4

---

2-Aminomethylinosine (1), a one-carbon extended homolog of an exocyclic amino group of guanosine, was synthesized from guanosine by the use of a newly developed protection and deprotection method. Introduction of a methoxy group into the 6-position of 2-benzenesulfonyl-purine riboside facilitated a nucleophilic substitution with cyanide to afford 2-cyano-6-methoxypurine riboside (11) which was subsequently hydrogenated and demethylated with trimethylsilyl iodide to afford 1.

著者

坂田 紳二 米井 清志郎 吉野 宏

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.7, pp.2583-2585, 1982-07-25 (Released:2008-03-31)

参考文献数

11

被引用文献数

7 10

---

A new method for the synthesis of 2-substituted 6-methylpurine ribosides from guanosine is described. Reaction of N (2), O (2'), O (3'), O (5')-tetraacetyl-O (6)-p-toluenesulfonylguanosine with carbanion from ethylacetoacetate gave the 6-ethoxycarbonylmethyl derivative, which was further converted to 2-amino-6-methylpurine riboside by deacetylation and decarboxylation. Replacement of the amino group of the compound by the fluoro group was achieved by the Schiemann reaction. The fluoro group could easily be replaced by several nucleophiles. As a result, 2-methylthio-, and 2-dimethylamino-6-methyl-9-β-D-ribofuranosylpurines could be effectively prepared.

著者

菊川 清見 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.21, no.5, pp.1151-1155, 1973-05-25 (Released:2008-03-31)

被引用文献数

8 14

著者

林 清五郎 植木 寛 原野 誠子 小宮 順子 井山 駿 原野 一誠 宮田 勝昭 新形 邦宏 米村 嘉郎

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.11, pp.1271-1276, 1964-11-25 (Released:2008-03-31)

被引用文献数

2 3

---

Dimethanesulphonylthioalkanes and analogous compounds were synthesized by the reaction of corresponding sodium thiosulphonate and appropriate dibromide to test the carcinostatic activity compaed with Myleran. It was found that some of these compounds inhibited pronouncedly the growth of the solid tumor produced by Ehrlich ascites carcinoma cells.

著者

田之口 真理子 加島 竜彦 雑賀 英之 井上 大志 有本 正生 山口 秀夫

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.1, pp.68-72, 1989-01-25 (Released:2008-03-31)

参考文献数

31

被引用文献数

11 16

---

Two new lignans, hernolactone (1) and fernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in recemic forms. Firstly, (±)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups. Synthesis of 2 was pursued using the corresponding 4-phenyl-1, 2-dihydronaphthalene lactone(18). The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22). Subsequent hydrogenation of 22 followed by acidification with concetrated hydrochloric acid gave isopicrobernanadin (21), leaving the 2, 3-trans, 3, 4-cis hydroxy acid (23), which was lactonized by means of N, N-dicyclohexylcarbodiimide to afford (±)-2.

著者

田之口 真理子 細野 江津子 北岡 真由子 有本 正生 山口 秀夫

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.7, pp.1873-1876, 1991-07-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

8 11

---

Two kinds of lignans were isolated from the seeds of Hernandia ovigera L. in addition to the nine lignans previously reported. One was confirmed as (-)-dimethylmatairesinol (11) and the other was identified as 5'-methoxypodorhizol (14) by comparison with the anthentic sample. An attempt at the cyclization of 14 afforded two compounds which were determined to be isohernandin (15) and an isomer of 15, 2-hydroxymethy 1-5, 6-methylenedioxy-7-methoxy-4-(3', 4', 5'-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthoic acid lactone (16).

著者

山口 秀夫 有本 正生 中島 淳二 田之口 眞理子 深田 能成

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.5, pp.2056-2060, 1986-05-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

10 11

---

Epipodophyllotoxin (EPT) and podophyllotoxin (PT) were prepared from desoxypodophyllotoxin (DPT), obtained from the seeds of Hernandia ovigera L. (Hernandiaceae) EPT was obtaind together with dehydrodesoxypodophyllotoxin (I) by a radical bromination of DPT with N-bromosuccinimide (NBS) followed by hydrolysis of the resultant 1-bromo-DPT, which was confirmed to be a mixture of 1α- and 1β-bromo compounds (7 : 3). EPT was oxidized with pyridinium chlorochromate to give podophyllotoxone (IV). The stereoselective reduction of IV to afford PT was examined with a variety of reagents, and borane-tert-butylamine complex was found to be effective.

著者

山口 秀夫 中島 淳二 有本 正生 田之口 真理子 石田 寿昌 井上 正敏

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.5, pp.1754-1760, 1984-05-25 (Released:2008-03-31)

参考文献数

18

被引用文献数

2 5

---

Two kinds of 4-aryltetralin type lignans, β-peltatin-A methyl ether (I-A) and β-peltatin-B methyl ether (I-B), were synthesized from desoxypodophyllotoxin (DPT), which is available in large quantities from the seeds of Hernandia ovigera L. (Hernandiaceae). The syntheses were achieved via demethylene-DPT (IV), 8-bromo-demethylene-DPT (V) and 8-bromo-DPT (VI). Methylenation of V was carried out successfully by using cesium fluoride and methylene iodide in DMF. Compound I-B was readily obtained by the reaction of VI with cuprous iodide and sodium methoxide in the presence of pyridine. Synthesis of I-A was only achieved by the reaction of lithiated VI with nitrobenzene at-100°C in the presence of tetramethylethylene diamine, and I-A was obtained in low yield, together with I-B.

著者

山口 秀夫 有本 正生 田之口 眞理子 石田 寿昌 井上 正敏

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.9, pp.3212-3218, 1982-09-25 (Released:2008-03-31)

参考文献数

22

被引用文献数

12 21

---

Two kinds of lignans were isolated from the seeds of Hernandia ovigera L. (Hernandiaceae) besides the previously reported desoxypodophyllotoxin (DPT), desoxypicropodophyllin, bursehernin and podorhizol, and the structures of the lignans were clarified. One, C23H24O8, named hernandin, was identified as 5-methoxy-desoxypodophyllotoxin (I) by both chemical and X-ray crystallographic methods. The other, C22H18O7, was obtained by purification of a previously isolated impure substance, mp 270-275°C. This compound was identified as 1, 2, 3, 4-dehydrodesoxypodophyllotoxin (II). This is the first report of the natural occurrence of II in plants.

著者

MARIKO TANOGUCHI MASAO ARIMOTO HIDEYUKI SAIKA HIDEO YAMAGUCHI

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.10, pp.4162-4168, 1987-10-25 (Released:2009-10-19)

参考文献数

21

被引用文献数

17 29

---

Three kinds of lignans, including a new lignan, named hernolactone, were isolated from the seeds of Hernandia ovigera L. besides six previously reported lignans, desoxypodophyllotoxin (DPT), desoxypicropodophyllin, bursehernin, podorhizol, hernandin and dehydro-DPT. The structure of hernolactone was determined as (2R, 3R) -3- (4′-hydroxy-3′, 5′-dimethoxybenzyl) -2- (3″, 4″, 5″-trimethoxybenzyl) -γ-butyrolactone (IV) and the other two lignans were identified as (-) -yatein ((-) -deoxypodorhizon) (V) and dehydropodophyllotoxin (IX).

著者

井藤 千裕 松井 卓哉 呉 天賞 古川 宏

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.5, pp.1318-1321, 1992-05-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

10 19

---

6, 7-Demethylenedesoxypodophyllotoxin (1) was isolated from the seeds of Hernandia ovigera L. (Hernandiaceae) collected in Taiwan, together with several known lignans. This is the first example of the occurrence of 1 in a natural source. The assignments of the 13C-nuclear magnetic resonance signals of several podophyllotoxin analogues isolated from this plant were also established by means of two-dimensional H-C correlation spectroscopy (COSY) and H-C long range COSY techniques.

著者

Yoshiaki Kato Kenji Niiyama Hideki Jona Shigemitsu Okada Atsushi Akao Shouichi Hiraga Yoshimi Tsuchiya Koji Tomimoto Toshiaki Mase

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.50, no.8, pp.1066-1072, 2002 (Released:2002-08-01)

参考文献数

16

被引用文献数

6 8

---

An asymmetric synthesis of a selective endothelin A receptor antagonist 1b is described. Asymmetric conjugate addition of aryllithium derived from 18 to the chiral oxazoline 17 followed by hydrolysis afforded 15 in 96% ee via purification as (S)-(−)-1-phenylethylamine salt. Pd(OAc)2/dppf (1,1′-bis(diphenylphosphino)ferrocene) catalyzed carbonylation followed by chemoselective addition of aryllithium derived from 23 which gave ketone 24. Diastereoselective reduction of the ketone with catecholborane followed by concomitant activation of the resulting alcohol and cyclization gave the late intermediate 26. Introduction of amino moiety on the pyridine ring by imidoyl rearrangement followed by deprotection and purification by crystallization furnished the enantiomerically pure target molecule 1b in 8% overall yield from 16.

著者

広田 耕作 丸橋 和夫 浅尾 哲次 千田 重男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.9, pp.3377-3379, 1982-09-25 (Released:2008-03-31)

参考文献数

15

被引用文献数

4 8

---

Thermolysis of 6-azido-1, 3-dimethyluracil (1) in formamide gave 1, 3, 6, 8-tetramethylpyrimido [5, 4-g] pteridine-2, 4, 5, 7 (1H, 3H, 6H, 8H)-tetrone (3), while the same reaction in N, N-dimethylformamide (DMF) gave 3-(5-amino-1, 3-dimethyluracil-6-yl)-4, 6-dimethyl-[1, 2, 3] triazolo [4, 5-d] pyrimidine-5, 7 (4H, 6H)-dione (4), which was converted into 3 in refluxing formamide. Compound 4 was also obtained by the treatment of 1 with 4, 6-dimethyl [1, 2, 3] triazolo [4, 5-d] pyrimidine-5, 7 (4H, 6H)-dione (5) in refluxing DMF. The mechanism of these reactions is discussed.

著者

伊藤 豊 矢野 真吾 渡辺 和夫 山中 悦二 相見 則郎 坂井 進一郎

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.6, pp.1702-1706, 1990-06-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

10 19

---

We investigated the selectivities and structure requirements for alpha-1 and alpha-2 adrenoceptor blocking activities of yohimbine (YO) and its 12 related analogs, such as β-yohimbine (β-YO), dihydrocorynantheine (DHC) and (-)indoloquinolizidine ((-)IQ). The affinity of YO analogs to alpha-adrenoceptor was assessed by measuring their blockade of pressor responses to epinephrine in pithed rats. Among YO structure groups, the potency order was YO>DHC=β-YO>geissoschizine methylether>14β-hydroxy YO>14β-benzoyloxy YO (inactive). (-)IQ was slightly less potent than YO, but much stronger than (+)IQ. Among (±)IQ structure groups, the potency order was (±)IQ>(±)1, 12b-trans-1-hydroxy IQ»(±)1, 12b-cis-1-hydroxy IQ (imactive). (±)Borrerine was active, but (±)desmethylborrerine was inactive. The alpha-1 blocking activities of the four compounds YO, β-YO, DHC and (-)IQ, were assessed in experiments of pressor responses to methoxamine in pithed rats and contractile responses to methoxamine in the rat vas deferens. The potency order was (-)IQ>YO>DHC>β-YO. Furthermore, the alpha-2 blocking activities of the four analogs were assessed in experiments of pressor responses to clonidine and inhibition of electrically driven cardioacceleration by clonidine, in pithed rats. The potency order was YO>β-YO>(-)IQ>DHC. Based on the potency ratio between alpha-1 and alpha-2 blocking activities, DHC or YO was most selective for alpha-1 or alpha-2 subtype, respectively, among the four YO analogs. These results suggest that the A, B, C and D rings of YO analogs and their planarity are necessary for the affinity to alpha-adrenoceptors and that the predominant conformation of the carboxymethyl or hydroxy group on the E ring of YO structure determines the selectivity for alpha-1 and alpha-2 blocking activities.

著者

伊藤 豊 矢野 真吾 渡辺 和夫 山中 悦二 相見 則郎 坂井 進一郎

出版者

公益社団法人日本薬学会

雑誌

Chem Pharm Bull (Tokyo) (ISSN:00092363)

巻号頁・発行日

vol.38, pp.1702-1706, 1990

被引用文献数

2

---

We investigated the selectivities and structure requirements for alpha-1 and alpha-2 adrenoceptor blocking activities of yohimbine (YO) and its 12 related analogs, such as β-yohimbine (β-YO), dihydrocorynantheine (DHC) and (-)indoloquinolizidine ((-)IQ). The affinity of YO analogs to alpha-adrenoceptor was assessed by measuring their blockade of pressor responses to epinephrine in pithed rats. Among YO structure groups, the potency order was YO>DHC=β-YO>geissoschizine methylether>14β-hydroxy YO>14β-benzoyloxy YO (inactive). (-)IQ was slightly less potent than YO, but much stronger than (+)IQ. Among (±)IQ structure groups, the potency order was (±)IQ>(±)1,12b-trans-1-hydroxy IQ≫(±)1,12b-cis-1-hydroxy IQ (imactive). (±)Borrerine was active, but (±)desmethylborrerine was inactive. The alpha-1 blocking activities of the four compounds YO, β-YO, DHC and (-)IQ, were assessed in experiments of pressor responses to methoxamine in pithed rats and contractile responses to methoxamine in the rat vas deferens. The potency order was (-)IQ>YO>DHC>β-YO. Furthermore, the alpha-2 blocking activities of the four analogs were assessed in experiments of pressor responses to clonidine and inhibition of electrically driven cardioacceleration by clonidine, in pithed rats. The potency order was YO>β-YO>(-)IQ>DHC. Based on the potency ratio between alpha-1 and alpha-2 blocking activities, DHC or YO was most selective for alpha-1 or alpha-2 subtype, respectively, among the four YO analogs. These results suggest that the A, B, C and D rings of YO analogs and their planarity are necessary for the affinity to alpha-adrenoceptors and that the predominant conformation of the carboxymethyl or hydroxy group on the E ring of YO structure determines the selectivity for alpha-1 and alpha-2 blocking activities.

著者

山中 悦二 成嶋 真弓 犬飼 邦江(旧姓長島) 坂井 進一郎

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.1, pp.77-81, 1986-01-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

7 13

---

Convenient syntheses of 1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo[2, 3-α]quinolizine derivatives (4a, b) and a relatd unsaturated lactam (14) are described. The condensation of tryptamine (1) with 8a, b (prepared from 7a, b by decarboethoxylation), followed by treatment with alkali gave the lactams (4a, b), respectively. The stereochemistry of 4b was determined by conversion to the known cis- and trans-compounds (5b). The condensation of 1 with the sulfenylated ester (10), which was prepared in two ways, followed by treatment with alkali gave the lactams (12a, b). Oxidation of 12a, b with m-chloroperbenzoic acid gave the sulfoxides (13) which were heated at 50°C to give the lactams (14, 15) and the pyridone (16).