HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Special Issue
Keiichiro Fukumoto's Special Issues, Vol. 77, No. 2, 2009
Published online: 9th September, 2008
■ Synthesis and Properties of 2-Bromo-7-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)-2,4,6-cycloheptatrine-1-one
Kanji Kubo,* Akira Mori, and Hitoshi Takeshita
*School of Dentistry, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan
Abstract
2-Bromo-7-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)tropone (1) was found to display unique absorption spectral changes in the presence of guest cations. The compositions of 1 with guest salts were 1:1 for Mg(SCN)2, Ca(SCN)2, and Ba(SCN)2, 1:2 for CdI2 and 1:1.5 for Zn(SCN)2, respectively. Azacrown ether (1) could be used as a carrier for transport of Hg2+ through a chloroform liquid membrane.
Published online: 14th October, 2008
■ Geranyl Derivatives of Salsolinol Show Increased Biological Activities
Kinuko Iwasa,* Suguru Okada, Yumi Nishiyama, Sousuke Takeuchi, Masataka Moriyasu, Chisato Tode, Makiko Sugiura, Atsuko Takeuchi, Harukuni Tokuda, Kazuyoshi Takeda, Yi-Nan Liu, Pei-Chi Wu, Kenneth F. Bastow, Toshiyuki Akiyama, and Kuo-Hsiung Lee
*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan
Abstract
Salsolinol and its N- and N,N-geranylated derivatives were tested for antimicrobial, cytotoxic, anti-oxidant, and anti-HIV activities, as well as inhibitory activity against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. N,N-Geranylation increased potency in three different assays, antimicrobial, cytotoxic, and EBV-EA, while N-geranylation increased potency to a lesser extent in these same assays. N,N-Geranylated salsolinol was significantly active in all assays, except anti-HIV, and may be useful as a lead compound for developing potential chemotherapeutic agents.
Published online: 25th September, 2008
■ Synthesis of Piperazine Derivatives by Cp*Ir Complex-Catalyzed N-Alkylative Reactions of Ethanolamines
Kein-ichi Fujita, Yasushi Kida, and Ryohei Yamaguchi*
*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
Abstract
A new method for the synthesis of piperazine derivatives catalyzed by a Cp*Ir complex has been developed. Cp*Ir complex-catalyzed N-alkylative homocoupling reactions of N-benzylethanolamines give N,N’-dibenzylpiperazine derivatives. For example, the reaction of N-benzylethanolamine in the presence of [Cp*IrCl2]2 (2.5 mol%) and NaHCO3 (15 mol%) in toluene at 110 °C for 17 h gives N,N’-dibenzylpiperazine in 66% yield. Cp*Ir complex-catalyzed N-alkylative cross coupling reactions of Boc-protected diethanolamines with benzylamine also give N-benzyl-N’-Boc-piperazine derivatives in moderate to good yields.
Published online: 22nd September, 2008
■ Flavonoids from Eupatorium odoratum with Death Receptor 5 Promoter Enhancing Activity
Takashi Ohtsuki, Takahito Hiraka, Hiroyuki Kikuchi, Takashi Koyano, Thaworn Kowithayakorn, Toshiyuki Sakai, and Masami Ishibashi*
*Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
Sixteen flavonoids including two new ones (1 and 2) were isolated from the leaves of Eupatorium odoratum (Compositae) through bioassay-guided isolation. The chemical structures of 1 and 2 were established on the basis of spectroscopic analysis. Compounds 2, 7, 9, and 14 led to more than 2-fold increase in death receptor 5 (DR5) promoter activity at 17.5 or 35 μM.
Published online: 9th October, 2008
■ Two New Alkaloids from Bulbs of Lycoris squamigera
Mariko Kitajima, Eri Kinoshita, Noriyuki Kogure, and Hiromitsu Takayama*
*Laboratory of Molecular Structure and Biological Function, Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
A new crinine-type alkaloid, squamigine, and a norbelladine-type alkaloid were isolated from the bulbs of Lycoris squamigera (Amaryllidaceae), together with sixteen known alkaloids. Their structures were determined by spectroscopic analyses.
Published online: 24th September, 2008
■ First Total Synthesis of Crispine B by Nitro Aldol and the Bischler-Napieralski Reaction
Tomohisa Yasuhara, Naoko Zaima, Satoko Hashimoto, Masako Yamazaki, and Osamu Muraoka*
*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan
Abstract
A pyrrolo[2,1-a]isoquinoline alkaloid, crispine B, was firstly synthesized in 55% overall yield from 3,4-dimethoxyaldehyde via five steps by employing nitro-aldol reaction and the Bischler-Napieralski reaction.
Published online: 16th October, 2008
■ Synthesis of 7-Anilino-5,8-dimethylisoquinolines Having Electron-Attracting Group on Anilino Moiety
Yukinori Nagao,* Ryosuke Endo, Mizuho Tokumaru, and Koji Arimitsu
*Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan
Abstract
7-Amino-5,8-dimethylisoquinoline gave various 7-anilino-5,8-dimethylisoquinolines via a palladium-catalyzed coupling reaction with bromobenzenes having electron-attracting groups (NO2, F).
Published online: 14th October, 2008
■ Preparation of 5H,7H-Dibenz[c,e]oxepin-5-one Derivative through Reconstruction of the Lactone Ring
Hitoshi Abe,* Masatsugu Arai, Yasuo Takeuchi, and Takashi Harayama*
*Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan
Abstract
The systematic investigation of the efficient transformation of 6H-dibenzo[b,d]pyran-6-one into 5H,7H-dibenz[c,e]oxepin-5-one is described.
Published online: 27th October, 2008
■ Anomeric Samarium(III) Intermediates of N-Acetylneuraminic Acid from Anomeric 2-Pyridylsulfides
Adeline Malapelle, Zouleika Abdallah, Gilles Doisneau, and Jean-Marie Beau*
*Laboratoire de Synthese de Biomolecules, Institut de Chimie Moleculaire et Materiaux associe au CNRS, Université de Paris-Sud 11, Batiment 430, F-91405 Orsay Cedex, France
Abstract
Treatment of the anomeric 2-thiopyridyl derivative of N-acetylneuraminic acid (sialic acid or Neu5Ac) with samarium diiodide in the presence of aldehydes or ketones provides the corresponding C-sialylated derivatives in excellent yields. The efficiency of the reductive samariation of the anomeric 2-pyridylsulfide moiety in the Neu5Ac series does not require any cosolvent or additive. This samarium Reformatsky-like reaction from anomeric 2-pyridylsulfide derivatives of Neu5Ac provides an efficient and highly stereoselective access to α-2,6-C-disaccharides.