Regular Issue

Vol. 87, No. 11, 2013

15 data found. 1 - 15 listed
Contents | Regular issue | Vol 87, No. 11, 2013
Published online:
DOI: 10.3987/Contents-13-8711
Review | Regular issue | Vol 87, No. 11, 2013, pp. 2199 - 2224
Published online: 30th September, 2013
DOI: 10.3987/REV-13-779
Total Synthesis of Decahydrobenzo[d]xanthene Sesquiterpenoids Aureol, Strongylin A, and Stachyflin: Development of a New Strategy for the Construction of a Common Tetracyclic Core Structure

Tadashi Katoh*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


In this article, the total synthesis of rearranged sesquiterpenoid hydroquinones—aureol, strongylin A, and stachyflin—is reviewed with a particular focus on their methodology and strategy.

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Review | Regular issue | Vol 87, No. 11, 2013, pp. 2225 - 2248
Published online: 10th October, 2013
DOI: 10.3987/REV-13-782
Recent Syntheses of Proanthocyanidins

Hidefumi Makabe*

*Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minamiminowa-mura, Kamiina-gun, Nagano 399-4598, Japan


Recently proanthocyanidins have been paid much attention due to their significant biological activities and health benefitical effects. The author reviewed recent progress of the syntheses of proanthocyanidins including our work within this decade.

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Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2249 - 2266
Published online: 3rd October, 2013
DOI: 10.3987/COM-13-12799
A Novel Synthetic Approach towards 1H-Pyrazole-5-carboxylic Acid Derivatives Using 4-(4-Methylbenzoyl)-5-(4-methylphenyl)furan-2,3-dione

Elif Korkusuz,* Ismail Yıldırım, and Ertan Şahin

*Kayseri Vocational College, Erciyes University, Kayseri 38039, Turkey


The 1H-pyrazole-5-carboxylic acid derivatives were obtained by reactions of 4-(4-methylbenzoyl)-5-(4-methylphenyl)furan-2,3-dione with 2,4-dinitrophenyhydrazine. So, new derivatives of 1H-pyrazole-5-carboxylic acid which are potential biological active compounds, were synthesized for the first time. The structures of all new synthesized products were characterized by IR, 1H-, 13C NMR, APT, and 2D NMR (HETCOR, COSY) spectroscopic data and elemental.

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Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2267 - 2281
Published online: 3rd October, 2013
DOI: 10.3987/COM-13-12812
Synthesis of Tetrasubstituted Pyrrolidine Derivatives Employing β-Lactam as a Chiral Building Block

Genta Tadano, Koji Ishikura, and Keiji Tanino*

*Department of Chemistry, Graduate School of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan


A new method for constructing tetrasubstituted pyrrolidine derivatives using the known β-lactam as a chiral building block was developed. After construction of a carbapenem skeleton, the β-lactam moiety was cleaved to afford a multi-substituted pyrrolidine. The present method was employed for the synthesis of A-315675 analogs 1 and 2.

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Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2283 - 2297
Published online: 25th September, 2013
DOI: 10.3987/COM-13-12816

Rawdha Medyouni, Naceur Hamdi,* Anis Ben Hsouna, Abdullah Sulaiman Al-Ayed, Hussain Ali Soleiman, Fethi Zaghrouba, and Christian Bruneau

*Chemistry Department, College of Science, Qassim University, P.O.Box 8000, Saudi Arabia


The preparation of novel metal-free phthalocyanine and metallophthalocyanine complexes 6 and 7 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were prepared and characterized by cyclotetramerization of compounds 4 and 5 with the corresponding metal salts (Zn(OAc)2·2H2O, Co(OAc)2·4H2O, CuCl, Mn(OAc)2·4H2O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol whereby a mixture of four different structural isomers are obtained; two of these isomers, with C2"- and Cs,symmetry are isolated by HPLC and characterized by FT-IR, UV-vis, elemental analyses, 1H NMR and 13C NMR spectroscopies. The electronic spectra exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are more active against E. coli and S. aureus .

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Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2299 - 2317
Published online: 15th October, 2013
DOI: 10.3987/COM-13-12827
Synthesis and in vitro Antitumor Effect of New Vindoline Derivatives Coupled with Amino Acid Esters

Péter Keglevich, László Hazai, Álmos Gorka-Kereskényi, Lilla Péter, Judit Gyenese, Zsófia Lengyel, György Kalaus, Zsófia Dubrovay, Miklós Dékány, Erika Orbán, Ildikó Szabó, Zoltán Bánóczi, Csaba Szántay, Jr., and Csaba Szántay*

*Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Szt. Gellért tér 4, Hungary


10-Bromovindoline and its 14,15-dihydro- and 14,15-cyclopropano derivatives were coupled in the position 16 with (L)- and (D)-tryptophan methyl esters. The tryptophan derivatives of vindoline were synthesized starting from the 16-carboxylic acid hydrazides via the corresponding azides which were allowed to react with the amino acid esters. The new compounds showed antitumor activity against human leukemia (HL-60) cells in vitro.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2319 - 2332
Published online: 15th October, 2013
DOI: 10.3987/COM-13-12810
Hydrazones and 1,3-Thiazolidin-4-ones Incorporating Furoxan Moiety Synthesized from Eugenol, the Main Constituent of Ocimum sanctum L. Oil

Nguyen Huu Dinh,* Trinh Thi Huan, Hoang Thi Tuyet Lan, and Sang-Bae Han

*Department of Chemistry, Hanoi National University of Education, 136 Xuanthuy Hanoi, Vietnam


Two series of new hydrazones and 1,3-thiazolidin-4-ones incorporating furoxan moiety were synthesized from eugenol, the main component of Ocimum sanctum L. oil. The structure of these compounds was determined by IR, MS, 1H and 13C NMR analysis. All resonance signals of proton and carbon in the examined compounds are assigned using HSQC, HMBC and NOESY spectra. The hydrazones and the 1,3-thiazolidin-4-ones were tested for antimicrobial activities and almost all examined thiazolidinones displayed moderate activity against S. aureus and A. niger. Among screened hydrazones only one compound exhibited a significant cytotoxicity for human cancer cell line SW620.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2333 - 2341
Published online: 16th October, 2013
DOI: 10.3987/COM-13-12813
Synthesis of 1,4-Diarylfluorenone and 1,4-Diarylfluorene

Yanmei Wang, Qiancai Liu,* Xiaoli Xiong, Shiming Deng, Jun Zhang, Min Zhu, and Hangmin Ge

*Department of Chemistry, East China Normal University, 500 Dongchuan Rd., Minhang, Shanghai 200241, China


A novel synthetic route to 1,4-diarylfluorenone and 1,4-diarylfluorene is presented by starting with ninhydrin. The retro-Diels-Alder cycloaddition was employed as a key step to construct the target fluorenones, while a highly efficient reduction from 1,4-diarylfluorenones to 1,4-diarylfluorenes is developed by using of sodium sulfide nonahydrate as reductant. The final products are confirmed by 1H NMR, 13C NMR and mass spectrometry.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2343 - 2350
Published online: 3rd October, 2013
DOI: 10.3987/COM-13-12822
Synthesis of Some Pyrazole-Fused Pyrido[3,2-a]azulenes

Dao-Lin Wang,* Zhe Dong, Qing-Tao Cui, Fei-Fei Yang, and Wei Zhao

*Liaoning Key Laboratory of Synthesis and Application of Functional Compound, College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121001, China


Facile synthesis of 11H(2H)-4-oxopyrazolo[3’,4’:6,5]pyrido[3,2-a]azulene-10-carboxylates (3) via a domino reaction of 3-(dimethylamino)-2-(2-methoxy-1-ethoxycarbonylazulen-3-oyl)acrylonitrile (1) with hydrazines (2) in moderate to good yields. This reaction provides a new procedure for synthesis of pyridinone-fused azulenes.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2351 - 2360
Published online: 16th October, 2013
DOI: 10.3987/COM-13-12818
Efficient Organocatalytic Michael Addition Reaction of β−Ketoesters under High Pressure

Maya Moritaka, Keiji Nakano, Yoshiyasu Ichikawa, and Hiyoshizo Kotsuki*

*Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan


The Michael addition reaction of β−ketoesters was efficiently promoted by a cooperative dual catalyst system composed by DMAP and thiourea A under high-pressure conditions (0.8 GPa) in toluene. The expected relatively congested adducts of 1,5-dicarbonyl compounds were prepared in high to excellent yield.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2361 - 2368
Published online: 30th September, 2013
DOI: 10.3987/COM-13-12819
Synthesis of Dihydrooxepins by the Cycloaddition of 2-Amino-4,5-dihydro-3-furancarbonitriles with Dimethyl Acetylenedicarboxylate

Fumi Okabe, Hiroshi Maruoka,* Eiichi Masumoto, Toshihiro Fujioka, and Kenji Yamagata

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


A facile and efficient synthesis of dihydrooxepins is described. Treatment of readily available 2-amino-4,5-dihydro-3-furancarbonitriles with dimethyl acetylenedicarboxylate at room temperature caused smoothly a cycloaddition reaction, followed by a ring expansion, giving the corresponding dihydrooxepin derivatives.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2369 - 2384
Published online: 4th October, 2013
DOI: 10.3987/COM-13-12824
A New Method for Synthesis and Angiogenic Evaluation of Leteprinim Potassium and Its Novel Analogs

Norikazu Sakakibara, Ikuko Tsukamoto, Yohei Isono, Maki Takata, Ryoji Konishi, Yoshihisa Kato, and Tokumi Maruyama*

*Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki City, Kagawa 769-2193, Japan


We developed a novel pathway for the successful synthesis of leteprinim potassium 1, which is one of the candidate substances for treating Alzheimer’s disease, and subsequently synthesized 4 types of corresponding novel derivatives 2–5 that have hypoxanthine or 2-chloro-6-aminopurine as the nucleobase. We then determined the angiogenic activity of these compounds by using human umbilical vein endothelial cells. Compounds 1–4 showed no angiogenic potencies judging from statistical analysis, student’s t-test.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2385 - 2394
Published online: 16th October, 2013
DOI: 10.3987/COM-13-12825
Design and Synthesis of New Hybrid Triazine-Indole Derivatives as Potential Antimicrobial Agents against Hospital Resistant Strains

Raed Al-Qawasmeh,* Monther A. Khanfar, Mohamad H. Semreen, Raed Abu Odeh, and Taleb H. Al-Tel

*Department of Chemistry, Faculty of Science, The University of Jordan, Amman 11942, Jordan


A new series of antimicrobial [2-(5,6-diaryl-1,2,4-triazin-3-yl)-1H-indole] have been synthesized via microwave technology. The synthesized compounds were found to be potent against various clinical isolates of Gram-positive and Gram-negative bacteria as well as hospital resistant strains, MRSA and MSSA when compared to the drugs Cephtriaxone, Gentamycin and Levofloxacin.

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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp. 2395 - 2402
Published online: 16th October, 2013
DOI: 10.3987/COM-13-12845
Allylation of N,N-Acetal Derivatives Using Allyl Tin Regent in the Presence of Aluminum Chloride

Xiaonan Sun, Takanori Obu, Tatsuro Kijima, Satoshi Murakami, Shigeru Matsuba, Miho Kusakari, and Bunpei Hatano*

*Graduate School of Science and Engineering, Yamagata University, 3-16 Jonan 4-Chome, Yonezawa 992-8510, Japan


Allylation of N,N-acetal derivatives proceeded efficiently using allyl tin regent in the presence of aluminum chloride, giving homoallylamines in good yields. This allylation was applied for N,S-acetals to give the corresponding homoallylamines.

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15 data found. 1 - 15 listed