Regular Issue

Vol. 68, No. 11, 2006

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 68, No. 11, 2006, pp. 2243 - 2246
Published online: 8th September, 2006
DOI: 10.3987/COM-06-10849
Novel Formation of 1,2-Dithiolane-3-thione from β-Dithiolactone

Toshiyuki Shigetomi, Akiko Nojima, Kosei Shioji, Kentaro Okuma,* and Yoshinobu Yokomori

*Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan


The sulfurization of β-dithiolactone gave 1,2-dithiolane-3-thione via an ionic intermediate. The reaction of 1,2-dithiolane-3-thione with acetylenedicarboxylate esters gave the corresponding spirocyclic 1,3-dithioles in good yields, whereas the reaction of 5-methyl-1,2-dithiole-3-thione with DMAD afforded a 1:2 cycloadduct in 78% yield.

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Communication | Regular issue | Vol 68, No. 11, 2006, pp. 2247 - 2252
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10863
Synthesis of 4-Arylpyrazoles via PdCl2(dppf)-Catalyzed Cross Coupling Reaction with Grignard Reagents

Hayato Ichikawa,* Yuuki Ohno, Yoshihide Usami, and Masao Arimoto

*Osaka University of Pharmaceutical Sciences, Nasahara Takatsuki, Osaka 569-1141, Japan


4-Aryl-1-tritylpyrazoles were prepared from the cross coupling reaction of aryl Grignard reagents with 4-bromo-1-tritylpyrazoles in the presence of 0.2 mol% PdCl2(dppf) as catalyst. To deprotect the trityl group, 4-phenyl-1-tritylpyrazole was reacted with TFA to produce 4-arylpyrazole in quantitative yield.

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Communication | Regular issue | Vol 68, No. 11, 2006, pp. 2253 - 2257
Published online: 3rd October, 2006
DOI: 10.3987/COM-06-10871
Microwave-Assisted Cycloaddition Reaction of Azides to N-Substituted 2-Azabicyclo[2.2.1]hept-5-en-3-ones

Minoru Ishikura,* Miyako Hasunuma, Koji Yamada, and Reiko Yanada

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


The reaction of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-ones (ABH) (1) with azides (2,4) could be effected under microwave conditions, producing aziridine-fused ABH (3) and triazolines (5,6) in good yields.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2259 - 2267
Published online: 3rd October, 2006
DOI: 10.3987/COM-06-10841
Efficient Microwave Assisted Syntheses of Unsubstituted Cyclic Imides

Yousef M. Hijji* and Ellis Benjamin

*Department of Chemistry, Morgan State University, Baltimore, MD 21251.USA


A number of cyclic imides were synthesized from cyclic anhydrides using ammonium chloride (NH4Cl), and 4-N,N-dimethylaminopyridine (DMAP) or with ammonium acetate (NH4OAc) under microwave irradiation in both a mono-mode and a conventional microwave. Several substituted succinic anhydrides used as reactants were synthesized efficiently by Diels-Alder reactions of maleic anhydride with 1,3-cyclohexadienes in 63-82% for the mono-mode and 72-92% in the conventional microwave ovens. Cyclic imides were synthesized with yields from 50 - 98%.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2269 - 2283
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10842
Synthesis of Novel 1,3,4-Oxadiazin-5(6H)-ones and 2-Hydroxymethyl-1,3,4-oxadiazoles

Agnieszka Kudelko* and Wojciech Zielinski

*Department of Organic Technology and Petrochemistry, Silesian University of
Technology, Ul. Krzywoustego 4, PL-44101 Gliwice, Poland


Reactions of α-hydroxyacid hydrazides (benzilic, R- and S-mandelic) and triethyl orthoesters (orthoformate, orthoacetate, orthopropionate, orthobenzoate) in glacial acetic acid resulted in two groups of heterocyclic compounds, derivatives of 6-phenyl-1,3,4-oxadiazin-5-(6H)-one and 2 hydroxymethyl-1,3,4-oxadiazole. Their structures were confirmed by typical spectroscopic methods and X-Ray analysis. Spectral characteristic of the compounds and attempts to elucidate the mechanism are discussed.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2285 - 2299
Published online: 5th September, 2006
DOI: 10.3987/COM-06-10844
Synthesis, Crystal Structure Determination and Antiproliferative Evaluation of Novel Benzazoyl Benzamides

Kristina Starcevic, Irena Caleta, Dominik Cincic, Branko Kaitner, Marijeta Kralj, Katja Ester, and Grace Karminski-Zamola

*Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, Marulicev trg 20, HR-10000 Zagreb, Croatia


A series of benzazoyl-benzamides containing different substituents (7-17) were synthesized by condensation of 2-aminobenzazole derivatives (3a-6) with p-substituted benzoyl chlorides. All compounds were characterized by IR, 1H and 13C NMR, MS and elemental analysis. Crystal structure was determined for the compound (9). Some of the new synthesized compounds (7-17) were screened for antitumor activities. Based on presented in vitro screening results we may conclude that compounds (10, 15a, 15b and 16) showed accentuated cell growth inhibitory activity.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2301 - 2317
Published online: 1st September, 2006
DOI: 10.3987/COM-06-10845
Synthesis of Vinca Alkaloids and Related Compounds. Part 106. An Efficient Convergent Synthetic Pathway to Build Up the Ibophyllidine Skeleton II. Total Synthesis of (±)-Deethylibophyllidine and (±)-14-Epi-deethylibophyllidine

Flórián Tóth, György Kalaus,* István Greiner, Mária Kajtár-Peredy, Ágnes Gömöry, László Hazai, and Csaba Szántay*

*Department for Organic Chemistry, Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Gellért tér 4, H-1521 Budapest, Hungary


Starting from 2,3-dihydrofuran (7) we prepared aldehyde (5) which, in a [4+2] cycloaddition reaction with the tryptamine derivative (4) gave, as a final step, compound (10) having a D-seco-aspidospermane skeleton. We synthesized (±)-14-epi-deethylibophyllidine (3) via the mesylate (12) of alcohol (11) which had been obtained from 10, whereas the cyclization of the benzoate ester (15) resulted in (±)-deethylibophyllidine (2). We have managed to build up (±)-2 via the tetracyclic intermediates (16) and (20).

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2319 - 2326
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10853
Synthesis of New 1,2-Diphenyl-4,5-dihydro-3H-3-benzazepines

Chiaki Kaito, Kumiko Sakamoto, Mitsushi Sakamoto, Aiko Yamauchi, and Masaru Kihara*

*Faculty of Pharmaceutical Sciences, The University of Tokushima, 1-78, Sho- machi, Tokushima 770-8505, Japan


1,2-Diphenyl-4,5-dihydro-3H-3-benzazepine derivatives (2a-d) were synthesized via cyclization reaction of N-[2-(2-iodophenyl)ethyl]-α- phenylphenacylamines (5a-c) and (5e) with n-C4H9Li, followed by dehydration of the cyclization products, 1,2-diphenyl-1-hydroxy-3-methyl-2,3,4,5-tetrahydro- 1H-3-benzazepines (4a-d) with trifluoromethanesulfonic acid.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2327 - 2333
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10856
L-Proline-Catalyzed Asymmetric Aldol Condensation of N-Substituted Isatins with Acetone

Gang Chen, Ye Wang, Hongping He, Suo Gao, Xiaosheng Yang, and Xiaojiang Hao*

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


L-proline-catalyzed asymmetric aldol condensation of several isatin derivatives with acetone is reported. The desired products were obtained in highly yield with the ee among 30-79%. The substitutes of N can deeply effect the ee value of products, and a novel mechanism is also described.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2335 - 2342
Published online: 12th September, 2006
DOI: 10.3987/COM-06-10858
Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus)

Masayuki Yoshikawa,* Toshio Morikawa, Junji Tanaka, and Hiroshi Shimoda

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of β-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2343 - 2347
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10859
N,N,N’,N’-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an Efficient Promoter for One-Pot Conversion of N-Arylglycines to Sydnones in the Presence of NaNO2/Ac2O under Neutral Conditions

Davood Azarifar,* Hassan Ghasemnejad-Bosra, Ramin Ghorbani-Vaghei, and Mahmood Tajbaksh

*Department of Chemistry, School of Science, Bu-Ali Sina University, Postal Code 65174, Hamadan, Iran


N,N,N’,N’-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization in high yields (85-95%) under mild and neutral conditions.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2349 - 2356
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-10865
Regioselective Reaction of 2-Indolylcyanocuprates with Electrophiles

Minoru Ishikura,* Reina Uemura, Koji Yamada, and Reiko Yanada

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


The reaction of 2-indolylcyanocuprate with electrophiles was found to give rise to 2- and 3-substituted indoles in regioselective manner.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2357 - 2364
Published online: 6th October, 2006
DOI: 10.3987/COM-06-10868
Nankakurine B, a New Alkaloid from Lycopodium hamiltonii and Revised Stereostructure of Nankakurine A

Yusuke Hirasawa, Jun’ichi Kobayashi, Yutaro Obara, Norimichi Nakahata, Nobuo Kawahara, Yukihiro Goda, and Hiroshi Morita*

*Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa-ku, Tokyo 142-8501, Japan


A new Lycopodium alklaoid, nankakurine B (2), has been isolated from the club moss Lycopodium hamiltonii together with nankakurine A (1). Stereochemistry of 2 was elucidated by combination of NOESY correlations and chemical transformation. Stereostructure of 1 was revised to be the same as that of 2. Nankakurine A (1) induced secretion of neurotrophic factors from human astrocytoma cells.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2365 - 2373
Published online: 29th September, 2006
DOI: 10.3987/COM-06-10874
Synthesis of Pipecolic Acid and Baikiain

Meng-Yang Chang,* Yung-Hua Kung, and Tsun-Cheng Wu

*Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, R.O.C.


A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction and ring-closing metathesis.

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Note | Regular issue | Vol 68, No. 11, 2006, pp. 2375 - 2380
Published online: 8th September, 2006
DOI: 10.3987/COM-06-10831
Establishment of an Efficient Synthetic Route to 3,4:3’,4’-Bis(3,6,9-trioxaundecane-1,11-dioxy)benzil

Masaru Kimura,* Kun Shi, Koji Hashimoto, and Zhi Zhi Hu

*Department of Chemistry, Faculty of Science, Okayama University, Tsushima- Naka 3-1-1, Okayama 700-8530, Japan.


3,4:3’,4’-Bis(3,6,9-trioxaundecane-1,11-dioxy)benzil (1) [bis(crown ether)benzil] was prepared by three different routes in which the third route C, including the method of Sonogashira-coupling, was the most efficient method with the overall yield of 50%. Further, the method of synthesizing the novel compound 3,4:3’,4’-bis[3,4-(3,6,9-trioxaundecane-1,11-dioxy)]benzoin (6) [bis(crown ether)benzoin], which has not yet been prepared appropriately, was also provided.

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Paper | Regular issue | Vol 68, No. 11, 2006, pp. 2381 - 2386
Published online: 12th September, 2006
DOI: 10.3987/COM-06-10832
Synthesis of 2-Aminomethylpyridine Derivatives of Phosphazenes

Saliha Begeç* and Sümeyya Alatas

*Inönü University, Faculty of Science and Arts, Chemistry Department, 44280 Malatya, Turkey


Novel cyclophosphazenes (5-8) with pyridine side groups have been synthesized by the reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6 (1), with 2-amino-3-methylpyridine (2), 2-amino-4-methylpyridine (3) and 2-amino-5-methylpyridine (4). Di- and monosubstituted products (5, 6) were obtained from the reaction of 1 with 2 and 3, respectively. Both di- and monosubstituted products (7, 8) were obtained from 2-amino-5-methylpyridine with 1. The structures of the compounds (5-8) were defined by IR, 1H, 13C and 31P NMR spectroscopy and elemental analyses.

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Note | Regular issue | Vol 68, No. 11, 2006, pp. 2387 - 2402
Published online: 12th September, 2006
DOI: 10.3987/COM-06-10869
Synthesis and Antiviral and Antitumor Activities of 2H-[1,2,3]Triazolo[4,5-d]pyrimidines and 1H-, 2H-, and 3H-[1,2,3]Triazolo[4,5-d]pyrimidin-5(4H)-one-7(6H)-thiones

Rafiqul Islam and Tomohisa Nagamatsu*

*Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700-8530, Japan


This paper describes a facile synthesis of 2-aryl-2H-[1,2,3]triazolo- [4,5-d]pyrimidine-5,7(4H,6H)-diones (3a-o) and 7-amino-2-aryl-5-phenyl-2H- [1,2,3]triazolo[4,5-d]pyrimidines (6a-e) prepared by oxidative cyclization of 6- amino-5-arylazopyrimidine-2,4(1H,3H)-diones (2a-o) and 4,6-diamino-5- arylazo-2-phenylpyrimidines (5a-e) with CuSO4, respectively, and a reliable thionation of [1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (3a,e,f, 7a,b and 9) accomplished by the reaction with phosphorous pentasulfide or Lawesson’s reagent as well as evaluation of their antiviral and antitumor activities in vitro.

Review | Regular issue | Vol 68, No. 11, 2006, pp. 2403 - 2422
Published online: 22nd September, 2006
DOI: 10.3987/REV-06-610
Quaternary Benzo[c]phenanthridines Sanguinarine and Chelerythrine: a Review of Investigations from Chemical and Biological Studies

Zdenek Dvorák, Vlastimil Kubán, Borivoj Klejdus, Jan Hlavác, Jaroslav Vicar, Jitka Ulrichová, and Vilím Simánek*

*Department of Medical Chemistry and Biochemistry, Faculty of Medicine, Palacky University Olomouc, Hnevotinska 3, 77515 Olomouc, Czech Republic


Sanguinarine and chelerythrine are intensively studied biologically active alkaloids for their potentially useful medicinal properties, such as antimicrobial, antiinflammatory, and antitumoral activities. This article aims to review critically recent literature published on the chemical behavior, synthesis, analytical methods and biotransformation of both alkaloids.

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18 data found. 1 - 18 listed