著者

佐々木 茂貴

出版者

公益社団法人 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.60, no.5, pp.498-499, 2002-05-01 (Released:2009-11-13)

参考文献数

5

著者

飯田 博一 杉山 弘

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.58, no.10, pp.975-987, 2000 (Released:2009-11-13)

参考文献数

39

被引用文献数

2 3

---

By the completion of the human genome project, many diseases including cancer, hereditary and viral diseases can be understood by the DNA sequence level. Control of the specific gene expression will provide ultimate gene therapy. Minor groove binding polyamides containing N-methylpyrrole and N-methylimidazole amino acids exhibit promising performance based on the recognition of nucleic acid sequences. Various types of sequence-specific DNA binding agents are developed and used for the regulation of gene expression. We synthesized novel type of polyamide-alkylator conjugates. These synthetic compounds alkylated predetermined DNA sequences selectively, and also some of them possessed selective potency for certain cancer cell lines. In this review, we will focus on recent progress of minor groove binding polyamides that play important roles in the rational recognition of nucleic acid sequences. One of the future directions of rational design of molecular medicine in the post genome era is proposed.

著者

長瀬 敏雄

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.57, no.10, pp.888-897, 1999 (Released:2009-11-16)

参考文献数

40

被引用文献数

1 1

---

Medicinal chemistry efforts on optimization of the endothelin receptor antagonistic natural products toward highly potent and selective ETA, ETB or ETA/B dual receptor antagonists are summarized. In order to get adequate biological tools for elucidating physiological and/or pathophysiological roles of endothelin as well as to identify highly potent antagonists possessing appropriate profiles, liquid phase and solid phase peptide synthesis, and their modification have been carried out. During these efforts, we have realized physiological roles of endothelin and its receptors, and have confirmed drug discovery values of its receptor antagonists as clinical drugs to modulate various kinds of disease.

著者

大久保 満

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.55, no.6, pp.566-569, 1997-06-01 (Released:2009-11-16)

参考文献数

10

被引用文献数

2 3

---

A new indolocarbazole anticancer agent, NB-506 (6-N-formylamino-12, 13-dihydro-1, 11-dihydroxy-13-β-D-glucopyranosyl) -5H-indolo [2, 3-a] pyrrolo [3, 4-c] carbazole-5, 7 (6H) -dione) was developed. The total synthesis of NB-506 was successfully achieved with a new glycosylation reaction which was carried out in good yield with high β-selectivity. Moreover the Mitsunobu reaction was newly found to be a convenient method for synthesizing dissymmetric indolocarbazole glycosides at the glycosylation step.

著者

長瀬 博 藤井 秀明

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.64, no.4, pp.371-381, 2006-04-01 (Released:2010-10-20)

参考文献数

30

被引用文献数

1 3

---

A selective nonpeptidic δ opioid receptor agonist TAN-67, (4aS*, 12 aR*) -4 a- (3-hydroxyphenyl) -2-methyl-1, 2, 3, 4, 4 a, 5, 12, 12 a-octahydropyrido [3, 4-b] acridine was designed from the selective δ opioid receptor antagonist NTI on the basis of the message-address concept and the accessory site theory. (-) -TAN-67 is a potent and selective δ1 opioid receptor agonist and showed profound antinociceptive effect, cardioprotective effect, and antiarrhythmic effect. On the contrary, (+) -TAN-67 induced hyperalgesia, which is the opposite effect of the antinociception. Optical resolution of racemic TAN-67 and the synthesis of (4aS*, 8 aR*) -4 a- (3-methoxyphenyl) -2-methyl-6-oxodecahydroisoquinoline, the important intermediate ketone of TAN-67 synthesis were also described.

著者

奥山 彬

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.60, no.8, pp.794-799, 2002-08-01 (Released:2009-11-13)

参考文献数

8

被引用文献数

1

---

The key issue of the present drug development is to find the lead compound in the minimum time and cost by using all kinds of new and traditional technology such as genomic drug discovery, random High Throughput Screening (HTS), virtual screening, combinatorial chemistry, X-ray crystal analysis, molecular modeling and so on. It is crucial to build up efficiently Chemical Compound Library with wide diversity to be applied to HTS for any kind of biological activity. University Compound Project at Foundation for Education of Science and Technology was started on February 2002, to use more efficiently not commercially-available domestic and abroad University Compounds (UC) for the drug development by building up the University Compound Data Base (UCDB). So far, 60 chemists at 35 universities and institutes, and 12 companies have joined to the project. The project has collected about 29, 000 UCDB available to the participating companies for the selection of UC and would add about 10, 000 UCDB every year.

著者

石黒 正路 今城 精一

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.54, no.5, pp.427-436, 1996-05-01 (Released:2009-11-16)

参考文献数

30

被引用文献数

2 2

---

Complex structures of neocarzinostatin (NCS) and β-lactamase/β-lactam antibiotics were built using NMR and crystallographic data of the proteins. On binding of ligands to proteins, particular amino acid side chains as well as ligands show dynamic character to exhibit specific molecular recognition. NMR studies and conformational analysis of the Phe 78 side chain of NCS revealed that the Phe 78 residue plays a major role on the chromophore binding through conformational change of the side chain aromatic moiety. Crystal structures and computational modeling of the enzyme-ligand complexes indicated that at the active site, the carboxylate of β-lactam antibiotics induces the conformational change of the Lys 73 residue and acts as a trigger of the hydrolytic reaction (acylation). Modeling of the acyl-enzyme structures also suggested the role of a mobile water molecule at the active site for deacylation. Experimental (NMR and X-ray crystallography) and computational results provided a fruitful information about molecular interaction between proteins and ligands.

著者

石黒 正路 今城 精一

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.8, pp.722-731, 1984-08-01 (Released:2009-11-13)

参考文献数

52

被引用文献数

1 1

---

Recent application of three dimensional computer graphics technics has widely expanded to molecular modeling. This article describes a brief history of computer graphics use in molecular modeling, function of hardware and software and its application to molecular modeling in Suntory computer aided drug-design system.

著者

芝 哲夫

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.50, no.12, pp.1070-1073, 1992-12-01 (Released:2009-11-16)

被引用文献数

1

著者

端早田 隆

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.65, no.7, pp.715-716, 2007-07-01 (Released:2010-10-20)

参考文献数

11

被引用文献数

1 2

---

This short review describes the recent development on β-mannosidic bond formation. Though the formation of β-mannoside is rather difficult in chemical synthesis, following two useful representative methods are reported; 1) introducing an acetal moiety as an acceptor on a donor as the stereocontroling element for intramolecular β-mannosylation; 2) using a donor having cyclic acetal protecting group at O-4, 6 position. As for the later, it was reported that the introduction of propagyl group at O-2 position improved β-selectivity even if a donor having steric protecting group at O-3 position was employed. Catalytic and β-selective mannosylation is also noted.

著者

中野 眞汎

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.7, pp.665-671, 1984-07-01 (Released:2009-11-13)

参考文献数

18

被引用文献数

5 7

---

Poly (ethylene carbonate), poly (propylene carbonate), and poly (ethylene propylene carbonate) were examined as to their biodegradability, permeability, and drug release characteristics.Poly (ethylene carbonate) degraded but poly (propylene carbonate) did not in the peritoneal cavity of rats and the peritoneal cavity and subcutaneous tissue of guinea pigs. Mixtures of the two polymers degraded at a rate in proportion to poly (ethylene carbonate) content. Degradation rate in the peritoneal cavity was faster than that in subcutaneous tissue in guinea pigs.Membranes free from pores were obtained from poly (ethylene carbonate). Permeability of drugs through them depended on lipophilicity indicating role of solubility of the drugs in the membrane material for permeation.Release rate of tegafur from poly (ethylene carbonate) implants was faster than that from poly (propylene carbonate) implants. Blood level profiles were obtained after implantation of implants in rats.Microspheres containing local anesthetics were prepared by a solvent evaporation process and effects of drug content and polymer on release profiles were examined in vitro. Duration of local anesthesia after administration of dibucaine microspheres in guinea pigs was demonstrated.

著者

田村 類 高橋 弘樹 生塩 孝則

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.56, no.1, pp.22-33, 1998-01-01 (Released:2009-11-16)

参考文献数

16

被引用文献数

1 3

---

We have discovered the first case of accomplishment of an enantiomeric resolution by simple recrystallization of a series of racemic compounds [(±) forms] composed of a regular packing of (+) and (-) molecules in a crystal, although in principle this sort of enantiomeric resolution has been considered to be infeasible for more than a century since the discovery of chiral crystals by Pasteur and preferential crystallization of conglomerates by Gernetz which are a mixture of homochiral (+) and (-) crystals. We have designated this new enantiomeric resolution phenomenon as “Preferential Enrichment”. Here we report a distinct evidence that polymorphism between a racemic compound and a mixed crystal (solid solution), which consists of alternating alignment of the two homochiral dimers in a crystal, is responsible for the “Preferential Enrichment”, and we propose a mechanism of the phenomenon of the reversal of chirality in the deposited crystals, that is the essence of the “Preferential Enrichment”, on the basis of the polymorphic transformation during crystallization.

著者

安孫子 淳

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.61, no.1, pp.24-34, 2003-01-01 (Released:2009-11-13)

参考文献数

14

被引用文献数

2 5

---

Boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the gener-al belief that carboxylic esters are inert toward the conventional enolization conditions, propionate esters are shqwn to have adequate reactivity on the boron-mediated aldol reaction. More impor-tantly, the stereochemical course of the aldol reaction can be controlled by the judicious choice of the enolization reagents. Complementary anti- and syn-selective asymmetric aldol reaction of structurally related chiral esters are developed. Also, novel double aldol reaction is discovered with acetate esters, which provides a precursor to the synthesis of chiral triols of C3-symmetry. Extensive NMR experiments lead to characterize the first carbon-bound boron enolates and the novel doubly borylate enolates as intermediates of the double aldol reaction. A plausible mecha-nism of the double aldol reaction is proposed.

著者

佐藤 恒夫 安孫子 淳 正宗 悟

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.44, no.5, pp.384-404, 1986-05-01 (Released:2010-04-23)

参考文献数

89

被引用文献数

2 2

著者

佐藤 恒夫 安孫子 淳 正宗 悟

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.44, no.4, pp.309-325, 1986-04-01 (Released:2010-01-22)

参考文献数

46

被引用文献数

2 5

---

This account examines double asymmetric induction from theoretical and practical viewpoints. In the context of four major organic reactions-the aldol, Diels-Alder, catalytic hydrogenation, and epoxidation-it is shown that a double asymmetric induction can be analyzed in terms of the single asymmetric reactions of each of the two chiral reactants. A rule which qualitatively relates the results of these single asymmetric reactions with the outcome of the double asymmetric reaction is proposed. A powerful new strategy based on this rule for the predictable creation of new chiral centers is discussed and the use of this strategy for the synthesis of sugars and macrolides is presented.

著者

安孫子 淳

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.54, no.7, pp.564-573, 1996-07-01 (Released:2010-01-28)

参考文献数

28

被引用文献数

2 3

---

New chiral auxiliaries based on the isoxazolidine skeleton have been developed. Characteristic feature of these auxiliaries are : 1) High reactivity for asymmetric alkylations. 2) Acylation of the auxiliary with an acid chloride and an amine, or DCC condensation. 3) One step transformation of the reaction products to the corresponding chiral alcohols, aldehydes and ketones without loss of the stereochemical integrity with the recovery of the auxiliary. Asymmetric alkylation of chiral β-substituted alkanols via their triflates lead to the easy access to the “reduced polypropionate units” as well as the first synthesis of the marine natural product (+) -siphonarienone. Enantiomerically pure axially dissymmetric cyclohexylidene compounds were synthesized using asymmetric Horner-Emmons reaction of the phosphonate derived from the auxilliary.

著者

酒井 浄 中村 紀雄

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.36, no.2, pp.93-106, 1978-02-01 (Released:2009-11-13)

参考文献数

91

被引用文献数

2 2

---

Advances in Prostaglandin (PG) fields after the discovery of PGG2 and PGH2 are reviewed. Biological activities of PGG2, H2, I2 and TXA2 are briefly explained, and the synthetic studies on these new PGs reviewed. Improvements in the synthesis of primary PGs are also summarized.

著者

酒井 浄 末宗 洋

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.46, no.4, pp.334-343, 1988-04-01 (Released:2009-11-13)

参考文献数

48

被引用文献数

1 1

---

Starting with (+) - and (-) -limonenes as chiral synthons, syntheses of biologically active compounds such as prostaglandins, (+) -brefeldin A and nepetalactones have been studied. The key-step of these conversions is based on the stereoselective cyclization of 3, 4-disubstituted 4-pentenals into cis-3, 4-disubstituted cyclopentanones using the Rh (I) -complex.Ring cleavage and reconstruction of five and six membered rings under acetalization conditions are also discussed.

著者

周東 智 市川 聡 阿部 洋 松田 彰

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.66, no.1, pp.50-60, 2008-01-01 (Released:2010-06-28)

参考文献数

22

被引用文献数

2 4

---

Despite considerable progress and extensive effort, a general method for highly stereoselective glycosylation particularly for the 1, 2-cis-glycosylation has not yet been developed and therefore is required. The α/β-stereoselectivity in glycosylation can be affected by the steric and stereoelectronic (anomeric) effects around the anomeric center, which depend on the conformation of the glycosyl donor substrates. Therefore, we hypothesized that highly α- and β-selective glycosylation can be realized by employing conformationally restricted substrates. We showed that the α/β-stereoselectivity was significantly increased by the conformational restriction and was completely inverted by changing the substrate conformation from the 4C1-form into the 1C4-form in radical and nucleophilic C-glycosylation reactions as well as in O-glycosylation reactions. The conformational restriction of substrates also effectively facilitates the α- and β-selective radical cyclization reaction at the anomeric position. Using the method, C-glucoside trisphosphates designed as Ca2+-mobilizing agents were successfully synthesized.

著者

津江 広人 堀口 雅弘 田村 類 藤井 孝太郎 植草 秀裕

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.65, no.12, pp.1203-1212, 2007-12-01 (Released:2010-10-20)

参考文献数

88

被引用文献数

35 52

---

A single crystal X-ray diffraction method is the most powerful technique for the crystal structure determination of both organic and inorganic compounds. However, a number of organic compounds crystallize in a form of polycrystalline powder rather than a single crystal of suitable size and quality for X-ray crystallographic analysis. Recent remarkable developments of both software and hardware have turned X-ray powder diffraction method into another significant technique for solving crystal structure. In fact, not a few crystal structures solved from the powder diffraction data of organic compounds have been published in scientific papers. At the same time, however, it is also true that crystal structure solution from powder data is still a challenging subject; indeed, the structure solution cannot be executed in such an automatic manner as established in the single crystal method. In this article, we describe the details of the structure solution processes from X-ray powder diffraction data, together with the experimental know-how gained from our experiences.