Special Issue

Volume 50's Special Issues, Vol. 50, No. 1, 1999

74 data found. 61 - 74 listedFirst Previous
Note | Special issue | Vol 50, No. 1, 1999, pp. 445 - 452
Published online:
DOI: 10.3987/COM-98-S(H)10
Synthesis of Enantiopure (S)-Thieno[f]indolizidines

Stefan Marchalin, Fridrich Szemes, Nathalie Bar, and Bernard Decroix*

*Laboratoire de Chimie, Faculté des Sciences et Techniques, Université du Havre, 30, rue Gabriel Peri, 76600 Le Havre, France


The thieno[2,3(or 3,2)-f ]indolizidines (5a,b) were synthesized in four steps from ready available (S)-5-oxoprolines (1a,b) derivatives. The stereospecific reduction of (S)-thieno[f]indolizinediones (2a,b) was discussed and the optical purity of each compound was determined.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 453 - 462
Published online:
DOI: 10.3987/COM-98-S(H)11
Synthesis of Certain Quinolin-2(1H)-one α-Methylene-γ-butyrolactones as Potential Antiplatelet Agents

Yeh-Long Chen, Tai-Chi Wang, Kuo-Chang Fang, Nein-Chen Chang, and Cherng-Chyi Tzeng*

*School of Chemistry, Kaohsiung Medical University, 100 Shin Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


Certain quinolin-2(1H)-one derivatives with various α-methylene-γ-butyrolactones substituted at C(7)-position were synthesized and evaluated for their antiplatelect activity against arachidonic acid (AA)-, and platelet-activating factor (PAF)-induced aggregation in washed rabbit platelets. 7-Hydroxyquinoline 1-oxide was treated with acetic anhydride followed by the hydrolysis of 1.0 N NaOH to afford 7-hydroxyquinolin-2(1H)-one (6). The desired 7-[2,3,4,5-tetrahydro-4-methylene-5-oxo-2-furanyl)methoxy]-quinolin-2(1H)-ones (8a-e) were obtained from 6 via alkylation and the Reformatsky-type condensation. These quinolin-2(1H)-ones (8a-e), exhibited approximately five to seven times more potent than their coumarin counterparts against AA- and PAF-induced aggregation and are approximately two hundred times more potent than aspirin against AA-induced aggregation.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 463 - 467
Published online:
DOI: 10.3987/COM-98-S(H)16
Studies on Isocyanides and Related Compounds. A Facile Synthesis of 1-Substituted 3-Cyano-2-methoxy-3-phenylpyrroles

Ricardo Bossio, Stefano Marcaccini, Roberto Pepino,* and Tomás Torroba

*CNR, Centro di Studio Sulla Chimica e la Struttura dei Composti Eterociclici e lolo Applicazioni, c/o Dipartimento di Chimica Organica "Ugo Schiff", Universita di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy


A simple one-pot synthesis of 1-substituted 3-cyano-1,2-dihydro-2-oxo-4-phenyl-2H-pyrroles (8) based on the isocyanide chemistry is described. Compounds (8) undergo a facile O-methylation with diazomethane to give the corresponding 1-substituted 3-cyano-2-methoxy-4-phenylpyrroles (1).

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Note | Special issue | Vol 50, No. 1, 1999, pp. 469 - 478
Published online:
DOI: 10.3987/COM-98-S(H)18
Synthesis of Coumarin-3-O-acylisoureas by Different Carbodiimides

Leonardo Bonsignore,* Filippo Cottiglia, Silvio M. Lavagna, Giuseppe Loy, and Daniela Secci

*Dipartimento Farmaco Chimico Tecnologico, Universita di Cagliari, Via Ospedale 72, I-09124 Cagliari, Italy


The synthesis and isolation of some O-acylisourea derivatives are described. The reaction between coumarin-3-carboxylic aciads and diisopropyl- and di-tert-butyl-carbodiimides leads only to coumarin-isourea derivatives except for two reactions which lead, as by-products, also to coumarin-urea derivatives.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 479 - 483
Published online:
DOI: 10.3987/COM-98-S(H)32
Practical Synthesis of Quinoline Nucleus of NK-104

Mikio Suzuki, Keizo Tanikawa, and Ryozo Sakoda*

*Central Research Institute, Nissan Chemical Industries Ltd., 722-1 Tsuboicho, Funabashi, Chiba 274-8507, Japan


The development of practical synthetic procedure for a staple intermediate of NK-104, a highly advanced HMG-Co. A reductase inhibitor is reported.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 485 - 488
Published online:
DOI: 10.3987/COM-98-S(H)49
A New Manzamine Congener from Marine Sponge Amphimedon sp.

Masashi Tsuda, Daisuke Watanabe, and Jun'ichi Kobayashi*

*Graduate School of Pharmaceutical Science, Hokkaido University, Sapporo 060-0812, Hokkaido


A new manzamine congener, 1,2,3,4-tetrahydromanzamine B (1), has been isolated from a Okinawan marine sponge Amphimedon sp. and the structure including absolute stereochemistry was elucidated from spectroscopic data.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 489 - 497
Published online:
DOI: 10.3987/COM-98-S(H)51
Manganese(III) Acetate Initiated Oxidative Free Radical Reaction between 2-Aryloxy-1,4-naphthoquinones and Dialkyl Malonates

Sheow-Fong Wang, Che-Ping Chuang,* and Jia-Han Lee

*Department of Chemistry, Natioanl Cheng Kung University, Tainan, 70101, Taiwan, R.O.C.


A free radical reaction between 2-aryloxy-1,4-naphthoquinones and diakly malonates initiated by manganese(III) acetate is described. This reaction provides a new method for the synthesis of 6,11-dihydro-6,11-dioxo-benzo[b]xanthenes. With meta substituent on aryloxy ring, this reaction shows unusual high regioselectivity.

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Note | Special issue | Vol 50, No. 1, 1999, pp. 499 - 503
Published online:
DOI: 10.3987/COM-98-S(H)55
Bufobutanoic Acid and Bufopyramide, Two New Indole Alkaloids from the Chinese Traditional Drug Ch'an Su

Yoshiaki Kamano,* Hiroshi Morita, Rui Takano, Ayano Kotake, Toshihiko Nogawa, Hirohumi Hashima, Koichi Takeya, Hideji Itokawa, and George R. Pettit

*Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka, Kanagawa259-1293, Japan


Two new bioactive indole alkaloids, 5-hydroxytryptamine (serotonin) N-4-oxobutanoic acid and 5-hydroxytryptamine N-acetyl-N-pyrrolecarboxamide, named as bufobutanoic acid (2) and bufopyramide (3), respectively, were isolated from the Chinese traditional drug Ch’an Su in a addition to known bufotenine (1). The structures were elucidated on the basis of spectroscopic data. Bufobutanoic acid (2) and bufopyramide (3) exhibited cytotoxicity against murine P388 lymphocytic leukemia cells with IC50 values of 22μg / mL and 7.6μg / mL, respectively.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 505 - 541
Published online:
DOI: 10.3987/REV-98-SR(H)2
Heteroatom Radical Addition-Cyclization and Its Synthetic Application

Takeaki Naito

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan


Heteroatom radical and heteroatom-mediated addition-cyclizations of the substrates including various types of multiple bonds are reviewed from a synthetic point of view.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 543 - 559
Published online:
DOI: 10.3987/REV-98-SR(H)3
Progress in Total Synthesis of Marine Alkaloids, Aaptamines

Eiichi Sugino, Tominari Choshi, and Satoshi Hibino*

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


A bright yellow aaptamine, which possesses a novel 1H-benzo[d,e][1,6]naphthyridine skeleton was isolated as a protonic salt from the Okinawan sea sponge Aaptos aaptos. Also related compounds, demethylaaptamine and demethyloxyaaptamine were isolated from same origin. We summarize here eight total syntheses containing one formal synthesis of aaptamine and related compounds.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 561 - 593
Published online:
DOI: 10.3987/REV-98-SR(H)4
Chemical Realization of the Biogenetic Pathways Proposed for the Fused-polycyclic Ethers of Marine Origins

Kenshu Fujiwara, Nobuyuki Hayashi, Tetsuo Tokiwano, and Akio Murai*

*Department of Chemistry, Graduate School of Sience, Hokkaido University, Sapporo 060-0810, japan


The biomimetic constructions of fused polycyclic ethres of marine origins according to the proposals for their biogenetic pathways starting from trans-polyepoxide compounds could be realized chemically as the model experiments in two ways : one is regarded epoxy groups as electrophiles as electrophiles and other is those as nucleophiles.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 595 - 609
Published online:
DOI: 10.3987/REV-98-SR(H)5
Limonoids from Melia toosendan (Meliaceae) and Their Antifeedant Activity

Munehiro Nakatani

*Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan


Twenty two new limonoids have been isolated along with nineteen known limonoids from a Meliaceae plant Melia toosendan and their antifeeding activity was tested against the larvae of Spodoptera insects. The structures, 13CNMR data and antifeedant activity of the isolated compounds are summarized.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 611 - 625
Published online:
DOI: 10.3987/REV-98-SR(H)6
Synthesis and Reactivity of Pyronoids in Aqueous Medium

Francesco Fringuelli,* Oriana Piermatti, and Ferdinando Pizzo

*Dipartimento di Chimica, Laboratorio di Chimica Organica, Università de Perugia, Via Elce di Sotto 8, 06100 Perugia, Italy


The synthesis and reactivity in aqueous medium of compounds having the 2- and 4-pyrone subunits (pyronoids) are reviewed. The results obtained in aqueous medium are compared with those carried out in organic solvent.

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Review | Special issue | Vol 50, No. 1, 1999, pp. 627 - 639
Published online:
DOI: 10.3987/REV-98-SR(H)9
Recent Advances on Antitumor-active Benzo[c]phenanthridine Alkaloids

Tsutomu Ishikawa* and Hisashi Ishii

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Recent advances on antitumor-active benzo[c]phenanthridine alkaloids mainly focused on our synthetic works are described.

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74 data found. 61 - 74 listedFirst Previous