Regular Issue

Vol. 63, No. 4, 2004

20 data found. 1 - 20 listed
Communication | Regular issue | Vol 63, No. 4, 2004, pp. 759 - 764
Published online: 6th February, 2004
DOI: 10.3987/COM-03-9977
Well-divided and pH-Dependent Bimodal Chemiluminescence of 2-Methyl-6-phenyl-8-(4-substituted phenyl)imidazo[1,2-a]pyrazin-3(7H)-ones Induced by Superoxide Anion

Ryota Saito,* Chizuru Inoue, and Akira Katoh

*Department of Applied Chemistry, Seikei University, Musashino, Tokyo 180-8633, Japan


An unprecedented pH-dependent bimodal chemiluminescence of 2-methyl-6-phenyl-8-(4-substituted phenyl)imidazo[1,2-a]pyrazin-3(7H)-ones (1a and 1b) initiated by superoxide anion (O2·-) in phosphate buffer solutions is described. The intensity ratio of the bimodal luminescence due to two light-emitting species, the singlet-excited neutral 2-acetamido-5-phenyl-3-(4-substituted phenyl)pyrazine [1(2a)* or 1(2b)*] and its amide anion [1(2a-)* or 1(2b-)*], varied as the pH rose. The percentage of the anionic luminescence intensity [Ianion/(Ineutral+Ianion)] for 1a showed a good linear correlation with the pH value, demonstrating the usefulness of 1a as a pH indicator as well as an O2·- probe.

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Communication | Regular issue | Vol 63, No. 4, 2004, pp. 765 - 771
Published online: 9th February, 2004
DOI: 10.3987/COM-03-9989
Anodic Oxidation of Tetrahydro-β-carboline Derivatives: Formal Oxidation of Protonated Tertiary Amines

Loïc Planas, Thierry Martens, Florence Billon-Souquet, and Jacques Royer*

*UMR 8638 (CNRS-University Paris-5), Faculty of Pharmaceutical and Biological Sciences, 4 avenue de l'Observatoire, 75270 Paris cedex 06, France


A study of the anodic oxidation of indolic compounds in the tetrahydro-β-carboline series is described. Methoxylation at the α position of the C-3 indole ring was observed furnishing a convenient access to variously substituted products at that position. Nevertheless, this oxidation reaction was not general and very slight structural variation led to different chemical behavior corresponding to a formal oxidation of protonated tertiary amines.

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Communication | Regular issue | Vol 63, No. 4, 2004, pp. 773 - 778
Published online: 9th February, 2004
DOI: 10.3987/COM-03-9996
Use of Deoxo-Fluor for Double Cyclization to Bis-thiazolines. Limitations of This Agent for the Synthesis of Oxazolines

Laura Scarone, Diver Sellanes, Eduardo Manta, Peter Wipf, and Gloria Serra*

*Department of Organic Chemistry, Facultad de Química, UDELAR, Av. General Flores 2124, Casilla de Correo 1157, Montevideo, Uruguay


Double cyclizations to bis-thiazolines have been performed using the Deoxo-Fluor cyclodehydration agent. Some limitations of the use of Deoxo-Fluor for the synthesis of oxazolines are described.

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Communication | Regular issue | Vol 63, No. 4, 2004, pp. 779 - 784
Published online: 20th February, 2004
DOI: 10.3987/COM-04-10009
Synthesis of CMP-sialic Acid Mimics That Have 5-Fluorouracil for Cytosine and the C-Terminal's Peptide Bond for the Phosphate Group: Targeting Inhibitors of Sialyltransferases

Shinji Nakahara, Toru Tanaka, Kazuharu Noguchi, Kenji Nozaki, Shuichi Tsuji, Tsuyoshi Miura, and Tetsuya Kajimoto*

*Department of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei-shi, Tokyo 184-8588, Japan


Novel mimics of cytidine 5'-monophosphate-sialic acid (CMP-sialic acid) were designed and synthesized for targeting inhibitors of sialyltransferases on the basis of the phenomenon that the tautomerization of 5-fluorouracil from the lactam to the lactim form produces a structure similar to that of cytosine, and the C-terminal's peptide bond can be a bioisoster of a phosphate group. Since γ-N1-(5-fluorouracilyl)-β-hydroxy-α-L-amino acid, a key synthetic intermediate, was easily prepared using the enzyme-catalyzed aldol reaction, the synthesis of the mimics of the CMP-sialic acid was attained in a short step.

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Communication | Regular issue | Vol 63, No. 4, 2004, pp. 785 - 790
Published online: 20th February, 2004
DOI: 10.3987/COM-04-10016
Synthesis of Microcarpalide, a Microfilament Disrupting Agent

Ken Ishigami and Takeshi Kitahara*

*Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan


Microcarpalide is a strong microfilament disrupting agent. The convergent and stereoselective synthesis of microcarpalide was succeeded via Julia olefination and macrolactonization.

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Paper | Regular issue | Vol 63, No. 4, 2004, pp. 791 - 795
Published online: 30th January, 2004
DOI: 10.3987/COM-03-9937
A Simple and Efficient Synthesis of New 6-Arylimino-6H-indolo[2,1-b]quinazolin-12-ones under Microwave Irradiation

Javad Azizian,* Ali A. Mohammadi, F. Ardakani, Ali R. Karimi, and Mohammad R. Mohammadizadeh

*Department of Chemistry, Faculty of Science, Shahid Beheshti University, P.O. Box 19395-4716, Tehran, Iran


A ring opening and selective reaction of isatoic anhydride with isatin-3-imine in the presence of catalytic amount of KF-Al2O3, a reusable catalyst, to yield a novel series of 6-arylimino-6H-indolo[2,1-b]quinazolin-12-one under microwave irradiation, is described.

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Paper | Regular issue | Vol 63, No. 4, 2004, pp. 797 - 807
Published online: 6th February, 2004
DOI: 10.3987/COM-03-9973
An Interaction of 2-Thiazoleacetonitriles with N-(2-Chloroacetyl)anthranilic Acid Ester

Elizaveta V. Resnyanska, Anton V. Tverdokhlebov,* Andrey A. Tolmachev, Yulian M. Volovenko, and Tatyana V. Shokol

*'Enamine Ltd.' Co., I. Kudri str. 31, apt. 17, 02042, Kiev, Ukranie


The title ester was found to react with 2-benzothiazoleacetonitrile yielding 3-(2-benzothiazolyl)-2,4-dihydropyrrolo[1,2-a]quinazoline-1,5-dione. At the same time 4-aryl-2-thiazoleacetonitriles gave 3,4-dihydro-β,4-dioxo- α,δ-bis(4-aryl-2-thiazolyl)-2-quinazolinepentanenitriles potassium salts under identical conditions. These results were explained in terms of different solubility of the intermediate compounds. Upon acidification the obtained salts were shown to undergo intramolecular Thorpe addition leading to the 3-amino-2,4-bis(4-aryl-2-thiazolyl)-4-[4(3H)-oxo-2-quinazolinyl]-2-cyclopenten-1-ones. Above mentioned pyrrolo[1,2-a]quinazoline derivative was treated with benzylamines and active methylene nitriles to yield β-(2-benzothiazolyl)-N-arylmethyl-3,4-dihydro-4-oxo-2-quinazolinepropanamides and 2-substituted 3-amino-4-(2-benzothiazolyl)-4-[4(3H)-oxo-2-quinazolinyl]-2-cyclopenten-1-ones, respectively.

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Paper | Regular issue | Vol 63, No. 4, 2004, pp. 809 - 818
Published online: 30th January, 2004
DOI: 10.3987/COM-03-9982
Some Reactions of 3-Phenyl-8-triphenylphosphoimino-1-azaazulene

Noritaka Abe,* Kentaro Nagamatsu, Kenji Tahara, and Hiroyuki Fujii

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yoshida, Yamaguchi 753-8512, Japan


Reaction of 3-phenyl-8-triphenylphosphoimino-1-azaazulene (1) with arylaldehyde gave 2-aryl-4-phenyl-3H-1,2a-diazacyclopent[cd]azulenes. Reaction of 1 with trans-cinnamaldehyde gave 3-benzyl-1-pheny-2a,5-diazabenz[cd]azulene as cyclization product. Cycloaddition reaction of 1 with dimethyl acetylenedicarboxylate gave tetramethyl 4-phenyl-9,9b-diazaindeno[4,3a,3,2-bcd]azulene-1,2,3,9a-tetracarboxylate and hexamethyl 6-phenyl-3aH-10c-azaacephenanthryene-1,2,3,3a,4,5-hexacarboxylate.

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Paper | Regular issue | Vol 63, No. 4, 2004, pp. 819 - 826
Published online: 9th February, 2004
DOI: 10.3987/COM-03-9984
Synthesis of 2,3,8-Trisubstituted 7H-Isoindolo[5,6-g]quinoxaline-5,7,9,11(8H)-tetraones

Heesoon Lee,* Sungmoon Cho, Byeonggil Choi, Kwon Namgoong, and Jae-Kyung Jung

*College of Pharmacy, Chungbuk National University, Cheongju 361-763, Korea


Oxidation of 3-methyl- or 7,8-dimethylbenzo[g]quinoxalinedione produced the unusual product, dihydroxybenezo[g]quinoxaline-5,10-dione- carboxylic acid or dicarboxylic acid. This process was used for the synthesis of a series of 2,3,8-trisubstituted isoindolo[5,6-g]quinoxalinetetraone derivatives.

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Paper | Regular issue | Vol 63, No. 4, 2004, pp. 827 - 844
Published online: 30th January, 2004
DOI: 10.3987/COM-03-9993
Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)

Miyuki Ishizaki,* Hiroshi Satoh, Osamu Hoshino, Kiyoshi Nishitani, and Hiroshi Hara*

*Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan


The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced aryl-bicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 845 - 850
Published online: 6th February, 2004
DOI: 10.3987/COM-03-9943
Conodusarine, a New Biologically Active Bisindole Alkaloid from Tabernaemontana divaricata

Toh-Seok Kam* and Huey-Shen Pang

*Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia


A new bisindole alkaloid of the vobasine-iboga type, conodusarine, was isolated from the stem-bark extract of Tabernaemontana divaricata and the structure established by spectroscopic analysis.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 851 - 860
Published online: 30th January, 2004
DOI: 10.3987/COM-03-9980
Sequential Bromination-Rearrangement of Push-pull Thiazolidines Induced by Pyridinium Hydrobromide Perbromide under Homogenous Reaction Conditions

Rade Markovic,* Marija Baranac, and Zdravko Dzambaski

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O.Box 158, 11001 Belgrade, Serbia and Montenegro


Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has the advantage of almost quantitative yields and a substantial rate enhancement.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 861 - 864
Published online: 20th February, 2004
DOI: 10.3987/COM-03-9981
A New Tricyclic 6-7-5-Ring Diterpene from Pliocene Fossil Tsuga dumosa

You-Xing Zhao, Cheng-Sen Li, Xiao-Dong Luo, and Jun Zhou*

*State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, China


A new diterpene named (+)-parryin-15,16-O-isopropylidene (1) and three known isopimara analogues (2-4) were isolated from the Pliocene lignified wood of Tsuga dumosa collected in Changning coalmine, Yunnan, China. Their structures were elucidated by spectroscopic analysis.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 865 - 870
Published online: 20th February, 2004
DOI: 10.3987/COM-03-9985
A Convenient Oxidation Method of the Benzylic 10-Position in 4,5-Epoxymorphinan

Hiromasa Horikiri and Kuniaki Kawamura*

*Pharmaceutical Research Laboratories, Toray Industries, Inc., 111 Tebiro, Kamakura, Kanagawa, 248-8555, Japan


A convenient oxidation method of the benzylic 10-position in 4,5-epoxymorphinan to obtain its 10-oxo derivatives is described. The reaction by using potassium permanganate proceeds in good yield and can be performed in large scale.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 871 - 877
Published online: 6th February, 2004
DOI: 10.3987/COM-03-9991
Two Lignan Glycosides from Vitis thunbergii

Yue-Hua He, De-Qiang Dou, Kenji Terashima, Yoshiaki Takaya, and Masatake Niwa*

*Faculty of Pharmacy, Meijo University, Tempaku, Nagoya 468-8503, Japan


Two new isolariciresinol-type lignan glycosides were isolated from Vitis thunbergii (Vitaceae) along with some oligostilbenes. Their structures were elucidated as (+)-3α-O-α-L-rhamnopyranosyl-5-methoxyisolariciresinol and (—)-3α-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosylisolariciresinol, respectively, on the basis of the spectral evidence

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 879 - 884
Published online: 6th February, 2004
DOI: 10.3987/COM-03-9994
A New Pterocarpan from Erythrina fusca

Pranorm Khaomek, Nijsiri Ruangrungsi,* Ekarin Saifah, Nongluksna Sriubolmas, Chikara Ichino, Hiroaki Kiyohara, and Haruki Yamada

*Faculty of Pharmaceutical Sciences, Chulalonghorn University, Bangkok 10330, Thailand


A new pterocarpan, 3-hydroxy-10-(3-hydroxy-3-methylbutyl)-9-methoxypterocarpan (1), together with seven known compounds, sandwicensin (2), erythrisenegalone (3), citflavanone (4), liquiritigenin (5), lonchocarpol A (6), lupinifolin (7) and 8-prenyldaidzein (8), were isolated from the stem bark of Erythrina fusca. The structure of 1 was determined on the basis of spectroscopic analyses. Among these compounds, lonchocarpol A (6) exhibited strongly antibacterial activities in vitro against Staphylococcus aureus, Bacillus subtilis and Enterococcus faecalis. Compounds (2, 3, 6 and 7) exhibited weakly antimycobacterial activity with minimum concentrations (MICs) of 100, 50, 50 and 25 μg/mL, respectively.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 885 - 893
Published online: 6th February, 2004
DOI: 10.3987/COM-03-10000
Synthesis of the ABCD Ring System of Azaspiracid, a Marine Poison from Mytilus edulis

Yuichi Ishikawa and Shigeru Nishiyama*

*Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan


Synthesis of the ABCD ring system of azaspiracid (1) was accomplished. The bridge system between the B and C rings using a sulfur atom, supported the spiroacetal-construction at the C13 position in the natural form. The stereochemistry was confirmed by the NOE experiments, along with conversion under acidic conditions into the unnatural derivative (12).

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 895 - 898
Published online: 20th February, 2004
DOI: 10.3987/COM-04-10004
Briaexcavatolide W, a New Diterpenoid from Briareum excavatum

Shwu-Li Wu, Ping-Jyun Sung, Jui-Hsin Su, Guey-Horng Wang, and Jyh-Horng Sheu*

*Department of Marine Resources, National Sun-Yat Sen University, Kaohsiung, 804, Taiwan, R.O.C.


A new briarane-type diterpenoid, briaexcavatolide W (1), has been isolated from the gorgonian coral Briareum excavatum. The structure was elucidated by spectroscopic methods.

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Note | Regular issue | Vol 63, No. 4, 2004, pp. 899 - 902
Published online: 20th February, 2004
DOI: 10.3987/COM-04-10013
(Delphinidin 3-Gentiobiosyl) (Luteorin 7-Glucosyl) Malonate from the Flowers of Eichhornia crassipes

Kenjiro Toki, Norio Saito, Shinya Tsutsumi, Chihiro Tamura, Atsushi Shigihara, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo, Japan


An additional new pigment exhibiting anthocyanin and flavone disubstituted malonate structure, was isolated from the blue-purple flowers of Eichhornia crassipes as a minor anthocyanin. This pigment was identified as (6'''-O-(delphinidin 3-O-(6''-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl))) (6''-O-(luteolin 7-O-( β-D-glucopyranosyl))) malonate by chemical and spectroscopic methods. The λmax of this pigment is 547 nm in 0.1% HCl-MeOH, where the negative cotton effect is also observed as similar to that of Eichhornia anthocyanin A, (delphinidin 3-gentiobiosyl) (apigenin 7-glucosyl) malonate previously isolated from the same flowers. This result supports that the new pigment also takes a folding conformation between delphinidin (chromophore) and luteorin (co-pigmnet).

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Review | Regular issue | Vol 63, No. 4, 2004, pp. 903 - 974
Published online: 30th January, 2004
DOI: 10.3987/REV-03-574
Syntheses of Heterocyclic Compounds under Microwave Irradiation

Yu Xu and Qing-Xiang Guo*

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


Microwave technique has been applied extensively in organic syntheses. In this paper, syntheses of different kinds of heterocyclic compounds under microwave irradiation were reviewed.

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20 data found. 1 - 20 listed