Special Issue

John Daly's Special Issues, Vol. 79, No. 1, 2009

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1081 - 1086
Published online: 6th November, 2008
DOI: 10.3987/COM-08-S(D)27
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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1087 - 1091
Published online: 21st November, 2008
DOI: 10.3987/COM-08-S(D)56
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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1093 - 1100
Published online: 4th December, 2008
DOI: 10.3987/COM-08-S(D)61
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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1101 - 1105
Published online: 5th December, 2008
DOI: 10.3987/COM-08-S(D)62
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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1107 - 1112
Published online: 8th December, 2008
DOI: 10.3987/COM-08-S(D)65
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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1113 - 1120
Published online: 9th December, 2008
DOI: 10.3987/COM-08-S(D)69
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 TESOTf2,4,6-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.

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Note | Special issue | Vol 79, No. 1, 2009, pp. 1121 - 1126
Published online: 19th December, 2008
DOI: 10.3987/COM-08-S(D)72
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.

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