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
John Daly's Special Issues,Vol. 79, No. 1, 2009
Published online: 6th November, 2008
■ Preparation and Electrochemical and Optical Properties of Tetrakis(dithiaselenolo)phthalocyanine
Takeshi Kimura,* Toshiharu Namauo, Akio Yamakawa, and Yutaka Takaguchi
*Center for Instrumental Analysis, Iwate University, 4-3-5 Ueda, Morioka, Iwate 020-8551, Japan
Abstract
Four o-xylylene groups of phthalocyanine (2) were removed by Birch reduction and the generated octathiolate anions were then reacted with Se to give tetrakis(dithiaselenolo)phthalocyanine (3). The dication generated from 3 in CHCl3/TFA was determined with UV-vis and NMR spectroscopy.
Published online: 21st November, 2008
■ Spirocyclization of Six-Membered Cyclic N-Acyliminium Ions with a Conjugated Diene
Hideki Abe, Yoshinori Muramatsu, Kazuhiro Watanabe, Sakae Aoyagi,* Chihiro Kibayashi, and Tadashi Katoh*
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
Intramolecular spirocyclization of six-membered cyclic N-acyliminium ions with a tethered conjugated diene has been studied. The reaction of an N-acyliminium ion bearing an endocyclic amide carbonyl group led to spirocyclization to give a 1-azaspiro[5.5]undecane compound.
Published online: 4th December, 2008
■ Syntheses and Evaluation as Glycosidase Inhibitor of 1,5-Dideoxy-1,5-imino-D-glucitol Analogs of Salacinol, a Potent α-Glucosidase Inhibitor Isolated from Ayurvedic Medicine, Salacia reticulata
Genzoh Tanabe, Takanori Hatanaka, Toshie Minematsu, Hisashi Matsuda, Masayuki Yoshikawa, and Osamu Muraoka*
*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan
Abstract
N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to inhibit both rat intestinal maltase and sucrase as strong as 1, while 10 has been reported to be inactive against glucoamylase G2 from Aspergillus niger. Its O-desulfate (12) was also found active against these enzymes, and characteristic sulfate anion moiety of 1 was found not essential for the α-glucosidase inhibitory activity.
Published online: 5th December, 2008
■ Nupharic Acid, a New Sesquiterpene Alkaloid from Nuphar japonicum
Noriyuki Kogure, Akiko Nozoe, Mariko Kitajima, 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 sesquiterpene alkaloid named nupharic acid (1) was isolated from the aerial part of Nuphar japonicum together with known alkaloids nupharidine (2) and deoxynupharidine (3). Alkaloid 1 is the first example of Nuphar alkaloids that lack the common furan moiety.
Published online: 8th December, 2008
■ Indole Alkaloids from the Leaves of Alstonia scholaris
Yusuke Hirasawa, Saori Miyama, Nobuo Kawahara, Yukihiro Goda, Abdul Rahman, Wiwied Ekasari, Aty Widyawaruyanti, Gunawan Indrayanto, Noor Cholies Zaini, and Hiroshi Morita*
*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
A new indole alkaloid, akuammidine-N-oxide (1) was isolated from the leaves of Alstonia scholaris (Apocynaceae) together with akuammidine (2), and the structure was elucidated by NMR spectral analysis and chemical correlation. Akuammidine (2) showed a moderate antiplasmodial activity.
Published online: 9th December, 2008
■ Organic Chemistry Using Weakly Electrophilic Salts: The Reaction with Nitrogen Nucleophiles
Hiromichi Fujioka,* Ozora Kubo, Kento Senami, Kazuhisa Okamoto, Takashi Okitsu, and Yasuyuki Kita*
*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan
Abstract
The reaction of electrophilc salts, which were obtained by the treatment of acetals with TESOTf―2,4,6-collidine, with nitrogen nucleophiles was studied in detail. Treatment of the salts with potassium phthalimide afforded the corresponding N,O-acetals in good yields. The use of hydrazine in place of potassium phthalimide gave the corresponding hydrazones. The reaction is very mild and chemoselective, and acid-labile functional groups can tolerate these conditions.
Published online: 19th December, 2008
■ Artopeden A, a New Antiplasmodial Isoprenylated Flavone from Artocarpus champeden
Tutik Sri Wahyuni, Wiwied Ekasari, Aty Widyawaruyanti, Yusuke Hirasawa, Hiroshi Morita,* and Noor Cholies Zaini*
*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
A new isoprenylated flavone, artopeden A (1) was isolated from the barks of Artocarpus champeden (Moraceae), and the structure was elucidated by NMR spectral analysis. Artopeden A (1) showed a potent antiplasmodial activity with an IC50 of 0.045 μg/mL against Plasmodium falciparum 3D7.