著者

西村 佐知夫

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.23, no.7, pp.612-619, 1965-07-01 (Released:2010-06-28)

参考文献数

73

被引用文献数

1 3

著者

内多 稔 小松 真 山崎 勝也

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.53, no.12, pp.1077-1089, 1995-12-01 (Released:2009-11-16)

参考文献数

29

被引用文献数

1 1

---

A novel series of N-acylamino acid analogues of 2 (1H) -quinolinone was synthesized and evaluated for antiulcer activity against acetic acid-induced gastric ulcer in rats. Out of this investigation, 2- (4-chlorobenzoylamino) -3- [2 (1H) -quinolinon-4-yl] propionic acid (rebamipide, OPC-12759) was identified The structureactivity relationships are discussed.Rebamipide did not only increase the healing rate of a chronic gastric ulcer model, acetic acid-induced gastric ulcer in rats, but also prevented recurrence and/or relapse of the ulcer in long term observation Rebamipide inhibited the formation of gastric mucosal lesions induced by various conditions. Rebamipide did not inhibit gastric acid secretion, although it potentiated gastric mucosal defensive factors such as mucus secretion, alkaline secretion, gastric mucosal blood flow and mucosal barrier. Rebamipide inhibited ethanol-induced gastric mucosal necrosis, which was completely abolished by pretreatment with indomethacin, suggesting the mucosal protective effect is associated with endogenous prostaglandins. Rebamipide inhibited production of superoxide from polymorphonuclear leukocytes and scavenged hydroxyl radical in vitro. Rebamipide showed useful efficacy on Helicobacter pylori-induced cell damage associated with activated neutrophils.The enantiomers of rebamipide were synthesized by using three efficient methods. Both enantiomers showed anti-ulcer activity against acetic acid-induced gastric ulcer and EtOH-induced gastric ulcer. The pair of enantiomers showed a small difference in activity.

著者

小槻 日吉三 隈本 康司

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.63, no.8, pp.770-779, 2005-08-01 (Released:2009-11-13)

参考文献数

85

被引用文献数

6 12

---

The great utility of high-pressure technology to achieve the desired reactions which are not readily accessible by other means and its application in natural product or material synthesis have been reviewed. Newly developed methods especially atom-economic processes for functional group transformations, environment-friendly constructions of target molecules, and promotion of sterically-restricted organic reactions are described. These include (1) Diels-Alder reaction, (2) intramolecular Diels-Alder reaction, (3) hetero-Diels-Alder reaction, (4) 1, 3-dipolar [3+2] cycloaddition reaction, (5) aldol condensation, (6) Friedel-Crafts-type alkylation, (7) Michael addition reaction, (8) SN2-type substitution, (9) nucleophilic aromatic substitution, (10) epoxide ringopening reaction, (11) organometallic reaction, (12) Lewis acid-catalyzed reaction.

著者

喜多河 庸二

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.18, no.7, pp.453-474, 1960-07-01 (Released:2010-10-20)

著者

石井 永

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.30, no.11, pp.922-941, 1972-11-01 (Released:2010-01-22)

参考文献数

81

被引用文献数

5 6

著者

覚知 豊次 横田 和明

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.48, no.12, pp.1106-1114, 1990-12-01 (Released:2009-11-13)

参考文献数

33

被引用文献数

5 4

---

Cyclopolymerization, which does not need a cyclic derivative as monomer, is a direct method for producing rings and polymer chain at the same time. Monomers forming 5-7 membered-rings have been generally studied. We established the synthesis of polymers with macrocyclic units via cyclopolymerization of bifunctional monomers containing oxyethylene units. Poly (crown ether) s and poly (cryptande) s are synthesized through the polymerizations of divinyl ethers and diepoxides, poly (thia-crown ether) s through diepisulfides, and poly (crown lactone) s through the monomers having acrylic and allylic groups. These polymers except for poly (crown lactone) s consist essentially of cyclic constitutional repeating units, and have the cation-binding properties. Cyclopolymerization of divinyl ethers is a facile method for producing optically active poly (crown ether) s which exhibit chiral recognition towards α-amino acids. For the cyclopolymerization of divinyl ether derived from chiral 3, 3'-disubstituted- 1, 1'-bi-2-naphthol, the asymmetric induction in the polymer main chain was concluded by the analysis of 1H NMR spectra of polymers.

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.11, no.12, pp.475-478, 1953-12-30 (Released:2010-10-20)

著者

室伏 旭

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.43, no.11, pp.991-1002, 1985-11-01 (Released:2009-11-13)

参考文献数

26

被引用文献数

1

---

Plant hormones are very important bio-active compounds which regulate the physiology of higher plants. There are five kinds of known plant hormones, auxin, gibberellin, cytokinin, abscisic acid and ethylene. Besides, there are some other plant hormone-like substances as brassinolide, polyamines and unknown flower-inducing substances. The studies of plant hormones concerning activity, practical use, fluctuation of endogenous level in intact plants, biosynthesis and structure-activity relationship are explained. The organic syntheses in these studies are important especially in production of plant hormones and their related compounds enough for their application test in the agricultural field, and various kinds of derivatization of plant hormones for the investigation of action mechanism and for the modern analysis methods with highest reliability and sensitivity. Some other importance of organic synthesis in plant hormone research is discussed.

著者

高橋 一公 伊達 隆文 山田 和俊 飯田 弘忠

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.29, no.3, pp.293-297, 1971

被引用文献数

1

---

A prolonged treatment of <I>p</I>-nitrotoluene and benzaldehyde with a sodium-hexamethylphosphoric triamide (HMPA) -benzene mixture was found to give 1-phenyl-2- (4-nitrophenyl) -ethan-1-ol (1) selectively. It was also found that the yield of (1) is sensitively affected by various factors, such as the temperature, the concentration of HMPA, and the reaction time. It may be concluded from the correlation of the yield of (1) and the conversion ratio of <I>p</I>-nitrotoluene that the formation of (1) results from the nucleophilic attack of the <I>p</I>-nitrobenzyl anion, derived from <I>p</I>-nitrotoluene, on the carbonyl carbon of benzaldehyde.

著者

斎藤 鐘次郎 立花 輝一 大道 弘昭

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.20, no.2, pp.150-157, 1962-02-01 (Released:2011-07-05)

参考文献数

23

被引用文献数

1

---

6-Methyl-6 (or 5)-hepten-2-one was synthesized from the addition compounds which were prepared from 4-methyl-l-penten-3-ol acetate or 2-methyl-4-penten-2-ol acetate and acetaldehyde by the Prins Reaction.These addition compounds weve at first hydrolysed to sec- or test-keto-alcohols respectively and then dehydrated to methyl heptenone under appropriate conditions in good yield. The dehydration of 6-methyl-5-hydroxy-2-heptanone was best carried out at 280-370°c by passing through a pyrex glass tube, packed with pumice catalyst containing phosphoric acid. 6-Methyl-6-hydroxy-2-hepta-none was dehydrated to 6-methyl-5-hepten-2-one with a trace of iodine. On the other hand, 6-methyl-6-hydroxy-2-heptanone acetate was subjected to pyrolysis at 450°c through a pyrex glass tube, filled with crushed glass in almost quantitative yield, giving 6-methyl-6-hepten-2-one. 6-Methyl-6-hydroxy-2-heptanone, reported by Verley in 1897, which was obtained by the hydration of methyl heptenone with 40-50% H2SO4, differed apparently from the hydrolygate of 6-methyl-6-hydroxy-2-heptanone acetate. The substance which was obtained by Verley's method, was supposed to be 2, 2-dimethyl-6-methyl-6-hydroxy-tetrahydro pyran. When 6-methyl-5-hydroxy-2-heptanone acetate was hydrolyged with alcoholic sodium hydroxide solution, 2-isopropyl-5-methyl-5-ethoxy-tetrahydrof uran and 6-methyl-5-hydroxy-2-heptanone were obtained. The f uran ring of the former could be opened easily to the latter keto-alcohol when it was boiled with dil. HCl.

著者

吉田 隆志 波多野 力 伊東 秀之

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.5, pp.500-507, 2004-05-01 (Released:2009-11-13)

参考文献数

24

被引用文献数

5 14

---

Large-size secondary metabolites with dimeric-oligomeric and/or dendrine-type structure from higher plants are regarded as natural nanomolecules which are constructed in a bottom-up pathway from small molecules under biological condition. Among them are polyphenols classified as tannins which have large molecular weights ranging from 500 to 4000, and strong affinity to proteins, alkaloids and heavy metals to form complex molecules (precipitates). They constitute two major groups : one is condensed tannins (proantocyanidins), which are composed of flavan-3-ol units linked through C-C bond, and the other is hydrolyzable tannins, which are principally multiple esters of D-glucose with gallic acid and its oxidative metabolites. This paper reviews the diverse structural characteristics of both tannins, especially ellagitannin oligomers up to pentamers, and examples of their biological activities. Formation of insoluble and soluble complex between tannins and proteins are also described.

著者

藤田 眞作

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.70, no.9, pp.951-957, 2012

被引用文献数

1

著者

生長 幸之助

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.72, no.1, pp.74-78, 2014-01-01 (Released:2014-03-04)

参考文献数

14

---

This article summarizes how “blog” media, which is complementary to traditional media (newspaper, television, academic journal etc.), is affecting and changing scientific communication processes especially in synthetic organic chemistry, through reviewing recent representative examples.

著者

川口 春馬

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.42, no.10, pp.922-931, 1984

被引用文献数

3

---

Research and development on the preparation of novel polymer microspheres and their applications have been accelerated in this decade. This article deals with polymer catalysts and reagents which have functional groups on and in polymer microspheres or beads. Immobilization of functional groups on polymer microspheres causes not only simplification of the recovery of reagent from the reaction system, but also changes in the rate, selectivity, and pattern of reaction in most cases. Dependence of these changes on the physical and chemical structure of polymer microspheres is discussed and a guide is given for the preparation of polymer microspheres having desirable functions.

著者

張 功幸 塩入 孝之 青山 豊彦

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.67, no.4, pp.357-368, 2009 (Released:2011-04-11)

被引用文献数

1 8

---

This review describes the recent application of trimethylsilyldiazomethane (Me3SiCHN2, TMSCHN2), its lithium and magnesium bromide salts [TMSC(Li)N2 and TMSC(MgBr)N2] to the synthesis of heterocycles. Reaction of TMSCHN2 with acyl isocyanates followed by Diels-Alder reaction with propiolates or N-phenylmaleimide affords furans or bicyclic pyridones in a one-pot process, respectively. In addition, TMSCHN2 is useful for the preparation of 2-azaazulenes, aziridines and indolizines. Meanwhile, TMSC(Li)N2 reacts with benzynes generated from halobenzenes to yield 3-trimethylsilylindazoles, which are easily converted to 1-arylindazoles or indazoles bearing 3-hydroxymethyl units. TMSC(Li)N2 is also applicable to the synthesis of indoles, benzofurans, pyrroles, thiophenes and 2,3-benzodiazepines. By using TMSC(MgBr)N2, α-substituted β-trimethylsilyl-α,β-epoxyesters can be synthesized from α-ketoesters in a one-pot process. Reaction of TMSC(MgBr)N2 with carbonyl compounds efficiently furnishes trimethylsilylated diazoalcohols, which react with propiolates to give di- or tri-substituted pyrazoles.

著者

Takashi Ikawa Hiroaki Tokiwa Shuji Akai

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.70, no.11, pp.1123-1133, 2012-11-01 (Released:2012-12-05)

参考文献数

86

被引用文献数

7 17

---

The silyl- and boryl-directed regiocontrol of benzyne reactions and their theoretical analyses using density functional theory (DFT) are described herein. The Diels-Alder reactions of both 3-silyl- and 3-borylbenzynes with substituted furans and the [3+2] cycloadditions of 3-silylbenzynes with 1,3-dipoles predominantly produced distal cycloadducts, whereas the [3+2] cycloadditions of the borylbenzynes exclusively produced proximal cycloadducts. Moreover, primary amines selectively underwent nucleophilic addition reactions at the more hindered ortho-position of the silyl group of the benzynes. The origin of these anomalous regiochemistries was theoretically evaluated using the natural bond orbital and reaction pathway analyses including the transition states of these reactions. On the basis of DFT calculations, it is proposed that the reactions of the borylbenzynes were controlled by the electrostatic effect of the boryl group, whereas those of the silylbenzynes were primarily governed by the steric effect of the silyl group.

著者

金井 求 松永 茂樹 生長 幸之助 清水 洋平

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.71, no.5, pp.433-442, 2013-05-01 (Released:2013-06-12)

参考文献数

63

被引用文献数

2

---

In general, biologically active drug lead molecules are structurally complex, bearing multiple functional groups and chiral sp3 carbons. Our aim in developing new catalysis is to promote a concise, robust, and clean drug lead synthesis. To do so requires catalysis allowing for the design of concepually new retrosynthesis independent of functional groups. Here we summarize our first step toward such a goal. First, we describe a Cu(I)-catalyzed enantioselective condensation of ketones and hemiaminals that can produce versatile chiral building blocks for alkaloid synthesis. The hard anion-conjugated soft metal (HASM) catalysis concept is the basis for the reactivity. Second, two Cu-catalyzed cross-dehydrogenative coupling (CDC) reactions are discussed. The radical-conjugated redox catalysis (RCRC) concept leads to the development of a very early example of catalytic asymmetric aerobic CDC. Third, the Rh-catalyzed aldehyde cross aldol reaction and the Co-catalyzed C-4 selective alkylation of pyridines, both of which are mediated by means of hydride transfer, are described. Unique reactivity in the latter two topics is partly due to the redox activity of the transition metal catalysts.

著者

飛鋪 靖

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.32, no.12, pp.971-988, 1974-12-01 (Released:2009-11-13)

参考文献数

118

被引用文献数

1 3

著者

福山 愛保 江角 朋之

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.65, no.6, pp.585-597, 2007-06-01 (Released:2010-10-20)

参考文献数

37

被引用文献数

9 17

---

Plants producing natural products remain one of the few sources of drug discovery, yielding unorthodox and often unexpected chemical structures. Since some classes of plant-derived natural products are frequently concentrated on the same genus, the extensive chemosystematic studies of the specific plants serve as a chemical library to discover candidates for drugs or biological probes for physiological studies. Vibsane-type diterpenes belong to rarely occurring natural products since they have been elaborated solely in Viburnum species such as V. awabuki, V odoratissimum, and V. suspensum. These diterpenes are further classified into 11-membered ring, 7-membered ring and rearranged (neovibsanin) types, thus putting their chemical diversity into a unique chemical library. We describe a variety of vibsanes, chemical correlations between three subtypes, and synthetic studies of vibsanin F, the simplest 11-membered ring vibsane, as well as neurotrophic activities of neovibsanins A-B.

著者

今村 寿一 青葉 千春 小島 邦彦

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.45, no.9, pp.909-913, 1987-09-01 (Released:2009-11-13)

参考文献数

60

被引用文献数

1 4

---

Tetramethylammonium hydroxide (TMAH) is a relatively strong base among organic compounds, and decomposes at 130-140°C into gaseous substances (Me3N, Me2O, MeOH, and H2O). TMAH has been prepared by alkali treatment of tetramethylammonium chloride (TMAC) obtainable from trimethylamine and methyl chloride, but use is made recently of developer electrolysis of TMAC in the presence of ion exchange membrane. The latter method gives rise to a highly pure TMAH aqueous solution free from chloride anions. TMAH currently finds some utilities in the production of highly functional materials such as developer for positive-working photoresist and the surface treatment of fibers, glasses, and plastics, and also as reagent for the methyl esterification of fatty acids and phospholipids, reagent for organic synthesis and preparation of catalysts, etc.