Regular Issue

Vol. 63, No. 1, 2004

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 63, No. 1, 2004, pp. 1 - 4
Published online: 14th November, 2003
DOI: 10.3987/COM-03-9911
Benzodioxole Chemistry. 5. Dramatic Substituent Effect in the Reaction of Carbonyl-bridged Cyclic Carbonates with Methoxide Ion

William S. Grove and Ernest A. Harrison Jr.*

*Department of Chemistry, The Pennsylvania State University, York Campus, 1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.


Benzodioxolediones (2c-e) undergo high-yield conversion to cyclopentenones (3c-e) in K2CO3/MeOH at room temperature, while analogs (2a) and (2b) yield exclusively cyclohexadiene carboxylates (1a and 1b) under these conditions. Isolation of intermediate 6(R,R’=Me R”=Ph) from the reaction of 2c with K2CO3/MeOH at 5-10 °C suggests that 3 is formed in a process triggered by attack of OMe(-) at the ester carbonyl of 2.

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Communication | Regular issue | Vol 63, No. 1, 2004, pp. 5 - 8
Published online: 14th November, 2003
DOI: 10.3987/COM-03-9924
Improvement in the Regioselectivity in the Ruthenium-catalyzed Metathesis Reaction of 2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH) with Allyltrimethylsilane

Minoru Ishikura,* Miyako Hasunuma, and Makoto Saijo

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1) with N-trialkylsilyl group was subjected to a ring-opening cross-metathesis reaction with allyl-trimethylsilane in the presence of a ruthenium catalyst, allowing the predominate formation of rel-(3R,5S)-3-(4,4,-dimethyl-4-silapentyl)-5-ethylpyrrolidin-2-one (5) over rel-(3R,5S)-5-(4,4,-dimethyl-4-silapentyl)-3-ethylpyrrolidin-2-one (6).

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Communication | Regular issue | Vol 63, No. 1, 2004, pp. 9 - 16
Published online: 10th November, 2003
DOI: 10.3987/COM-03-9925
New Synthesis and Biologically Active Molecular Design of Deazapteridine-Steroid Hybrid Compounds

Tomohisa Nagamatsu,* Hiroki Yamada, and Kazuyuki Shiromoto

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


This paper describes a facile and general synthesis of a new class of the hybrid compounds (4, 5 and 16), possessing 5-deazapteridine and steroid in the same ring system, by condensation of 6-(monosubstituted amino)uracils (9) or 6-(monosubstituted amino)-2-phenylpyrimidin-4(3H)-ones (14) with 2-hydroxy-methyleneandrostanolone (10) or 2-hydroxymethylenetestosterone (15) under heating in the presence of p-toluenesulfonic acid monohydrate and their potential unti-coccidiosis activities.

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Communication | Regular issue | Vol 63, No. 1, 2004, pp. 17 - 22
Published online: 21st November, 2003
DOI: 10.3987/COM-03-9928
Synthesis of Optically Active Tetrahydro-3-benzazepine-2-carboxylic Acid Derivatives via the Ring Expansion Reaction of Isoquinolines and Enzymatic Resolution

Yuji Koseki, Hidefumi Ozawa, Katsuaki Kitahara, Ichiro Kato, Hiroto Sato, Haruhiko Fukaya, and Tatsuo Nagasaka*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


The facial approach to 3-benzazepine-2-carboxylic acid derivatives (1) via the ring expansion reactions of 10b-hydroxymethyloxazoloisoquinolines (3) to 3-benzazepines (2) is described. Utilizing enzymatic resolution, the synthesis of (-)-(S)-N-Cbz-3-benzazepine-2-carboxylic acid (1b) was achieved.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 23 - 28
Published online: 31st October, 2003
DOI: 10.3987/COM-01-9163
Synthesis of N-Allyl and N-Propadienylacridones Using Phase-Transfer Catalysis

Lisbet Xuárez, Roland F. Pellón,* Norma D’Accorso, Verónica Montesano, and Mirtha Fasio

*Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina


A convenient procedure for the synthesis of N-allyl substituted acridones under phase-transfer catalysis is reported using allyl bromide as alkylating agent. When propargyl bromide was used, in the same reaction conditions, no propynylacridone was detected in the reaction and only propadienylacridone was obtained in moderate yield.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 29 - 39
Published online: 14th November, 2003
DOI: 10.3987/COM-03-9890
Bipyrrole Derivatives as New DNA-Minor Groove Binders

Mikimasa Tanada, Yoshihiro Shibata, Minoru Maeda, and Shigeki Sasaki*

*Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


Small molecules with capability of binding with DNA or RNA would have broad application as probes in genomic studies, and also as potential candidates for new therapeutic agents. In this study, we synthesized dithioamido-bipyrrole derivatives as new binding molecules to the duplex DNA. It has been revealed from the competitive binding experiments with the known intercalater, ethidum bromide, and the minor groove binder Hoechst 33258 that the dithioamido-bipyrrole derivatives with alkyl chains with medium length bind the duplex DNA in a similar manner with the minor groove binder. As ionic interactions are not included in the binding with the duplex DNA, the new dithioamido-bipyrrole skeleton may provide an interesting motif for DNA binding.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 41 - 54
Published online: 4th November, 2003
DOI: 10.3987/COM-03-9903
Indium-mediated Reductive Inter-molecular Coupling Reaction of 2-Nitroaniline with Aromatic Aldehydes to Benzimidazoles

Byeong Hyo Kim,* Rongbi Han, Ji Sook Kim, Young Moo Jun, Woonphil Baik, and Byung Min Lee

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea


2-Nitroaniline and aromatic aldehydes were coupled to give benzimidazoles in high yields in the presence of 2-bromo-2-nitropropane and indium at room temperature.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 55 - 62
Published online: 14th November, 2003
DOI: 10.3987/COM-03-9909
Synthesis and Structural Studies of (2-Oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic Acids

Anton V. Dolzhenko,* Nina V. Kolotova, Vladislav O. Kozminykh, Wai-Keung Chui,* Paul W. S. Heng, and Viktor N. Khrustalev

*Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore


(2-Oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acids (4a-c, 9a-c) were prepared from 2-aminopyridines by acylation with maleic or citraconic anhydrides and followed by Michael addition. Formation of 3-methyl substituted derivatives (9a-c) from citraconic anhydride was found to be regioselective. The molecular conformations of the products in the solution and in the crystal form were discussed based on 1H NMR spectral and X-Ray data.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 63 - 74
Published online: 10th November, 2003
DOI: 10.3987/COM-03-9916
Preparation and Structure of Diexo-Oxanorbornane-fused 1,3-Heterocycles

Ferenc Miklós, Iván Kanizsai, Steffen Thomas, Erich Kleinpeter, Reijo Sillanpää, and Géza Stájer*

*Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary


Via the reaction of diexo-oxanorbornanedicarboxylic anhydride with toluene, the diexo-aroylcarboxylic acid (3a) was prepared, which exists partly as the tautomeric lactol (3b). With bifunctional reagents, 3a yields fused hetero-cycles containing three–six rings. Thus, alkylenediamines result in imidazole- and 1,3-diazepine-fused oxygen-bridged isoindolones (6a,b), alkanolamines form the oxazole- and 1,3-oxazine-fused oxanorbornene derivatives (7a-c), and o-phenylenediamine undergoes cyclization to furnish the condensed benzimidazole (8). The reaction of 3a with diexo-aminonorbornanecarbohydrazide yields a pyrimido-pyridazine containing six condensed rings (9). In a similar reaction with diendo-aminonorbornenecarbohydrazide, cyclopentadiene cleaves off to give the tricyclic retro Diels-Alder product (10). The structures, and particulary the configurations at the oxanorbornane ring systems and the position of the aryl substituent, were established by means of 1D- and 2D-NMR spectroscopy and, for 3b and 7c, also by X-Ray measurements.

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Paper | Regular issue | Vol 63, No. 1, 2004, pp. 75 - 85
Published online: 14th November, 2003
DOI: 10.3987/COM-03-9918
Synthetic Studies on Isoquinoline Derivatives with Multidrug Resistance (MDR) Modulating Activity

Chen Ma,* Su-Dong Cho, J. R. Falck, and Dong-Soo Shin

*School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China


Tetrahydropyridazino-1,4-oxazinoisoquinoline derivatives with
multidrug resistance (MDR) modulating activity were designed and synthesized.
A key step for cyclization of 1,4-oxazine ring was developed using K2CO3 and
CH3CN in one-pot. Among prepared compounds, 2-(4-fluorobenzyl)-9,10-
[3,4,-a]isoquinolin-1(2H)-one (1f) exhibited significant MDR reversing activity
and low toxicity, which might be as potential MDR agent.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 87 - 93
Published online: 31st October, 2003
DOI: 10.3987/COM-03-9896
One-Pot Synthesis of Tetra-substituted Imidazoles on Silica Gel under Microwave Irradiation

Yu Xu, Yan-Zhi Liu, Lei Rui, Lei Liu, and Qing-Xiang Guo*

*Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei 230026, China


A new procedure for synthesis of tetra-substituted imidazoles was developed. A series of imidazole derivatives including six new compounds were synthesized by this procedure via condensation of benzoin, aromatic aldehyde, amine and ammonium acetate in the presence of silica gel under solvent-free microwave irradiation.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 95 - 105
Published online: 21st November, 2003
DOI: 10.3987/COM-03-9901
Synthesis of 2-Substituted 3,4-Dihydroquinazoline Derivatives via Regioselective Addition of a Carbon Nucleophile to a Carbodiimide

Bum Hoon Lee, Jae Yeol Lee,* Bong Young Chung, and Yong Sup Lee*

*Division of Life Sciences, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 131-650, Korea


Synthesis of 2-alkyl or phenyl-substituted 3,4-dihydroquinazoline derivatives (6) is described via regioselective carbon nucleophilic addition (RMgBr and RM) to a carbodiimide (4) followed by intramolecular conjugate addition.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 107 - 113
Published online: 4th November, 2003
DOI: 10.3987/COM-03-9902
Terpenoid Metabolites of the Marine Octocoral Eunicea laciniata

Kelly I. Marville, William F. Reynolds, R. Lynn Sealy, and Winston F. Tinto*

*Laboratory of Bioorganic Chemistry, Department of Biological & Chemical Sciences, University of the West Indies, Cave Hill Campus, P.O. Box 64, Bridgetown, Barbados


A chemical investigation of the Caribbean marine octocoral Eunicea laciniata collected along the south coast of Barbados afforded a new cubitane diterpenoid (1), a new steroidal glycoside (3), along with two known diterpenes. Their structures were determined by 1D and 2D NMR spectral experiments.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 115 - 121
Published online: 31st October, 2003
DOI: 10.3987/COM-03-9907
Two New Bicoumarins from Clausena excavata

Yuko Takemura, Kinuko Kanao, Asami Konoshima, Motoharu Ju-ichi,* Chihiro Ito, Hiroshi Furukawa, Harukuni Tokuda, and Hoyoku Nishino

*Faculty of Pharmacy, Meijo University, 150 Yagoto, Tempaku-ku, Nagoya, Aichi 468-8503, Japan


Two novel type bicoumarins, named cladimarins A (1) and B (4), were isolated from the branch of Clausena excavata (Rutaceae) collected in Indonesia. The structures were elucidated on the basis of spectroscopical data especially by using HMBC method. Naturally occurring bicoumarin, connected two coumarin moieties by acetal ring as in 1 and by ester bond as in 4, is rare type. Inhibitory effects of new bicoumarins on EBV-EA activation induced by TPA in Raji cells were also demonstrated.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 123 - 128
Published online: 21st November, 2003
DOI: 10.3987/COM-03-9915
Three New Lycoctonine-Type C19-Diterpenoid Alkaloids from Delphinium giraldii

Xian-Li Zhou, Qiao-Hong Chen, and Feng-Peng Wang*

*Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, No. 17, Duan 3, Remin Nan Road, Chengdu 610041, China


From the roots of Delphinium giraldii, three new lycoctonine-type C19-diterpenoid alkaloids, giraldine D (1), giraldine E (2) and giraldine F (3), have been isolated. The structures of 1~3 were established by spectroscopic evidence including 2D NMR spectroscopy.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 129 - 136
Published online: 10th November, 2003
DOI: 10.3987/COM-03-9917
A New Resveratrol Hexamer from Upuna borneensis

Tetsuro Ito,* Toshiyuki Tanaka, Zulfiqar Ali, Yukihiro Akao, Yoshinori Nozawa, Yoshikazu Takahashi, Ryuichi Sawa, Ken-ichi Nakaya, Jin Murata, Dedy Darnaedi, and Munekazu Iinuma

*Gifu Prefectrual Institute of Health and Environmental Sciences, 1-1 Nakafudogaoka, Kakamigahara, Gifu 504-0838, Japan


A new resveratrol hexamer, upunaphenol A, was isolated from an acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structure, which has twelve asymmetric carbon atoms on the partial structures of a dibenzobicyclo[3.2.1]octadiene ring and four dihydrobenzofuran rings, was determined by spectral analysis including 1D and 2D NMR spectral experiments. Resveratrol and four known resveratrol oligomers, ampelopsin F, isoampelopsin F, vaticanols C and B, were also isolated. Upunaphenol A was found to suppress cell growth in HL60 cells through induction of apoptosis with IC50 at 9.2 μM.

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Note | Regular issue | Vol 63, No. 1, 2004, pp. 137 - 143
Published online: 31st October, 2003
DOI: 10.3987/COM-03-9919
Preparation and Optical Resolution of a New Helical Lactone Carrying the 2,8-Dioxabicyclo[3.3.0]octane Ring System

Makoto Yamaye,* Yusuke Ikeda, Namiko Cho(Toh), Yoshinori Miura, Tetsutaro Yoshinaga, Katsuya Mukae, and Toshiaki Tsuru

*Faculty of Engineering, Kyushu Kyoritsu University, 1-8 Jiyugaoka, Yahatanishiku, Kitakyushu 807-8585, Japan


A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo[3.3.0]octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800° (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.

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Review | Regular issue | Vol 63, No. 1, 2004, pp. 145 - 173
Published online: 14th November, 2003
DOI: 10.3987/REV-03-569
Structural Revision in Pyrazole Chemistry

Devinder Kumar* and Shiv P. Singh*

*Department of Applied Chemistry, Guru Jambheshwar University, Hisar-125001, Haryana, India


Reaction of several heteroarylhydrazines with β-diketones has been incorrectly reported to generate triazepines or diazepines. It has now been firmly established that these reactions lead to the formation of pyrazoles. Further, many workers have reported the formation of pyrazoles in the reaction of heteroarylhydrazines with trifluoromethyl 1,3-diketones, whereas the actual products were found to be 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles. It was also established that with a trifluoromethyl β-diketone and hydrazines, the location of the CF3 group at position 3 or 5 of pyrazoles depends on the nature of the hydrazine. Erroneous reports concerning the structure of the products obtained by the reaction of dehydroacetic acid with hydrazines have also been revised.

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18 data found. 1 - 18 listed