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Published online: 22nd August, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13516
Microwave-Assisted Efficient Synthesis of 4-Substituted Amino-2-methylquinolines Catalyzed by p-Toluenesulfonic Acid

Xiao-qin Wang,* Yuan-hong Cai, Xiao-yang Xie, Cui-ying Huang, Jia-yu Li, Wen-na Chen, Ming-hua He, and Wen-jia Pan*

*School of Pharmacy, Guangdong Medical University, NO1, Xincheng Road, Songshan Lake, Dongguan 523808, China

Abstract

A series of novel 4-subtituted amino-2-methylquinolines (3a-3o) were readily synthesized via the reaction of 4-chloro-2-methylquinoline with amines catalyzed by p-toluenesulfonic acid (TsOH) at 120 for 1 h under microwave-assisted organic synthesis (MAOS) condition. The yields of product 3a-3o were in range of 55-89%. This approach has advantages such as higher yield, shorter reaction time, lower costs, more convenience, and higher efficiency compared to the conventional method. The structures of the products were characterized by using 1H NMR, 13C NMR and HRMS. The reactivity of different amines was discussed.

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Published online: 22nd August, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13513
Three New Benzolactones from the Leaves of Yunnan Local Sun Cured Tobacco and Their Bioactivities

Feng-Mei Zhang, Jian-Jun Xia, Pei-Song Yang, Qin-Peng Shen, Chun-Bo Liu, Pei He, Jia-Qiang Wang, Zhi-Hua Liu,* and Zhong-Tao Ding*

*Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industry Company, Hongjin Road 181#, Kunming, 650231, China

Abstract

Three new benzolactones, 5-(hydroxymethyl)-6-(2-oxopropyl)isobenzofuran-1(3H)-one (1), 5-methyl-6-(2-oxopropyl)isobenzofuran-1(3H)-one (2), and 5-methoxy-6-(2-oxopropyl)isobenzofuran-1(3H)-one (3), together with three known benzolactones (4-6) were isolated from the leaves of Yunnan local sun cured tobacco. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-3 were tested for their anti-tobacoo mosaic virus (TMV) activities and compounds 1-6 were tested for their cytotoxicity activities. The results revealed that compound 1-3 showed high anti-TMV activity with inhibition rate of 28.6, 31.2 and 32.7%. These rates are close to that of positive control. Compounds 1-6 also showed moderate-to-weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 2.5-8.5 μM.

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Published online: 18th August, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-16-845
Diazonaphthoquinones: Synthesis, Reactions and Applications

Dina I. A. Othman and Mitsuru Kitamura*

*Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550, Japan

Abstract

This review deals with synthesis and reactions of diazonaphthoquinones during the past 6 years. Various substituted diazonaphthoquinones have been prepared by the reaction of the appropriate naphthol and 2-azido-1,3 dimethyl imidazolinium chloride (ADMC) in short direct pathway. This method is likely to find wide spread uses in organic synthesis and material chemistry such as for preparing photoresists. In this review, different metal catalyzed reactions are investigated and applied successfully to the synthesis of important aromatic compounds. In addition, total synthesis of some natural compounds has been attempted using this recently developed diazo transfer methodology. It is hoped that this compilation, in combination with the previously published literatures on diazo-transfer reaction, will provide useful, up-to-date and comprehensive foundation and reference sources for individuals interested in the same field.

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Published online: 18th August, 2016

Communication | Regular issue | Prepress
DOI: 10.3987/COM-16-13515
Oxidative Dearomatic Cyclization of N-Substituted Benzanilide Derivatives: Conformational Effect of Amide Groups on the Reaction

Kousuke Hayashi, Jun Takayama,* Meiyan Xuan, Misaki Suda, Hiroyuki Teramae, and Takeshi Sakamoto*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

The synthesis of spirooxindoles with a hypervalent iodine reagent depended on N-substituted benzanilide derivatives as starting materials. Reaction yields of benzanilides containing various N-substituents were discovered to relate to the cis and trans conformations of the amide bond by ab initio molecular orbital calculations at the B3LYP/6-31G(d,p) and MP2/6-31G(d,p) levels, including full geometry optimizations. The relationship between the reaction and conformation of the starting material by quantum chemical calculations was applied to the formal synthesis of SR121463.

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Published online: 5th August, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-16-844
Efficient Synthesis of Heterocycles Using Highly Electrophilic Ethenetricarboxylates

Shoko Yamazaki*

*Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan

Abstract

The synthesis of heterocyclic compounds utilizing highly electrophilic ethenetricarboxylates is described. Ethenetricarboxylate is a member of methylenemalonates and more reactive than frequently used alkylidenemalonates by the electron-withdrawing effect of 2-carboxyl group. They are utilized as efficient Michael acceptors or electron-deficient C=C components. Lewis acids also promote the reactions of ethenetricarboxylate derivatives efficiently. The intermolecular and intramolecular reactions of ethenetricarboxylates towards synthesis of heterocycles are presented.

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Published online: 5th August, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)12
Synthesis of γ-Trifluoromethyl Tetronate Derivatives from Squarates

Yoshihiko Yamamoto,* Yosuke Takamizu, Takashi Kurohara, and Masatoshi Shibuya

*Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan

Abstract

Squarates and semisquarates were treated with TMSCF3 in the presence of a catalytic amount of AcONa in DMF at room temperature to afford 4-trifluoromethyl-4-hydroxycyclobutenones. Subsequent oxidative ring expansion of these products was performed using Pb(OAc)4 in the presence of MS 4A in 1,2-dichloroethane at 50 °C to afford γ-trifluoromethyl tetronate derivatives.

Supporting Info. (7MB)PDF (714KB)

Published online: 5th August, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13521
Three New Isoindolin-1-ones from the Leaves of Yunnan Local Sun Cured Tobacco and Their Bioactivities

Feng-Mei Zhang, Jian-Jun Xia, Pei-Song Yang, Qin-Peng Shen, Chun-Bo Liu, Pei He, Jia-Qiang Wang, Zhi-Hua Liu,* and Zhong-Tao Ding*

*Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industry Company, Hongjin Road 181#, Kunming, 650231, China

Abstract

Three new (1-3) and one known (4) isoindolin-1-ones were isolated from the leaves of Yunnan local sun cured tobacco. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-3 were tested for their anti-tobacco mosaic virus (anti-TMV) activities and compounds 1-4 were tested for their cytotoxicity activities. The results showed that compounds 1-3 showed high anti-TMV activity with inhibition rates of 43.8, 45.6 and 52.7%. These rates are higher than that of positive control. Compounds 1-4 also showed moderate-to-weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 2.8–8.2 μM.

Supporting Info. (490KB)PDF (794KB)

Published online: 3rd August, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)7
[3+2] Cycloadditions of N-Protected ‘(S)-Diazoproline’ with Selected Acetylenes

Grzegorz Mlostoń,* Paulina Pipiak, and Heinz Heimgartner*

*Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

Acetylene carboxylates and an acetylene phosphonate reacted with N-protected (S)-2-(diazoacetyl)pyrrolidines ((S)-diazoprolines) to give optically active bis-heterocyclic pyrazole derivatives in a regioselective [3+2] cycloaddition. The reactions occurred at 60 °C in THF solution in the absence of a catalyst. However, diethyl ethynylphosphonate reacted significantly slower than the carboxylates. The obtained products were shown to exist in CDCl3 solution at room temperature as mixtures of rotamers. The reactions of diethyl ethynylphosphonate with a selected cyclic α-oxodiazo compound, i.e. 2-diazoacenaphthen-1-one, yielded a fused tricyclic pyrazole derivative.

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Published online: 1st August, 2016

Communication | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)11
Oxidative Self-Annulation of 2,5-Diaryl-3,4-diaminothiophene via C–C and C–S Bond Cleavage of the Thiophene Ring: A New Synthesis of an Amino-Substituted Triarylthieno[3,4-b]pyrazines and Their Photophysical Properties

Youhei Takeda,* Satoshi Ueta, and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

A novel oxidative self-annulation of 2,5-diaryl-3,4-diaminothiophenes that accompanies C–C and C–S bonds cleavage of a thiophene ring to produce 3,5,7-triaryl-2-aminothieno[3,4-b]pyrazines in moderate to good yields has been discovered. Photophysical properties of this new family of thienopyrazines have also been disclosed.

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Published online: 1st August, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)10
Total Synthesis of Fargesine Using a Platinum-Catalyzed Intramolecular Friedel-Crafts-Type C–H Coupling–Allylic Amination Cascade

Yuito Tanaka, Yuta Suzuki, Yasumasa Hamada, and Tetsuhiro Nemoto*

*Pharmaceutical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba, Japan

Abstract

Total synthesis of fargesine was described herein. The synthesis was based on the platinum-catalyzed intramolecular Friedel-Crafts-type C–H coupling–allylic amination cascade to construct the 3,4-fused tricyclic indole skeleton.

Supporting Info. (306KB)PDF (415KB)

Published online: 28th July, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)8
N-Heterocyclic Carbene-Promoted [3+2] Cycloaddition of Allenyl Sulfone and Arylidenemalononitriles

Satoru Kuwano,* Toshinobu Masuda, Koki Yamaguchi, and Takayoshi Arai

*Department of Chemistry, Graduate School of Science, Chiba University, , Japan

Abstract

N-Heterocyclic carbenes promote the [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles, accompanied by 1,2-migration of the sulfonyl group. This reaction provides a new route to highly substituted cyclopentenes.

Supporting Info. (4.9MB)PDF (402KB)

Published online: 26th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13391
A Green, Solvent-Free One-Pot Synthesis of Disubstituted Quinolines via A3-Coupling Using 1 Mol% FeCl3

Shivani Naidoo and Vineet Jeena*

*School of Chemistry and Physics, University of KwaZulu-Natal, Cnr Golf and Ridge Roads 3209, South Africa

Abstract

A simple and green route towards disubstituted quinolines via A3-coupling using 1 mol% FeCl3 is described. Using this approach, the above-mentioned derivatives were synthesized in moderate to good yields (45-95%) under solvent-free, microwave conditions. Preliminary investigations have indicated that a further decrease in catalyst amount is possible with a satisfactory yield still observed.

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Published online: 26th July, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13514
Synthesis of 3-Hydroxy-1,3-dihydro-2H-pyrrolo[2,3-b]-, -[2,3-c]-, or -[3,2-c]pyridin-2-ones from the Respective N-Pyridinylpivalamides and α-Keto Esters

Kazuhiro Kobayashi,* Risa Kosuna, and Yuuki Chikazawa

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A convenient synthesis of the title compounds utilizing the reaction of the dilithium compounds, generated in situ by the reaction between N-(pyridin-2-, -3-, or -4-yl)pivalamides and two equivalents of butyllithium in THF, with α-keto esters is described. Thus, N-(3-lithiopyridin-2-yl)pivalamide reacts smoothly leading to the formation of the corresponding α-hydroxy esters. These undergo deprotective cyclization in refluxing hydrochloric acid to afford 3-substituted 3-hydroxy-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones. Similarly, starting from N-(pyridin-3- or -4-yl)pivalamides, the corresponding 3-dihydro-2H-pyrrolo[2,3-c]- or -[3,2-c]pyridin-2-one derivatives, respectively, can be prepared.

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Published online: 21st July, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13508
A Facile Preparation of Imidazo[1,2-a]pyridin-3-amine Derivatives via a Three-Component Reaction with β-Cyclodextrin–SO3H as Catalyst

Jian Wu,* Fang-Zhou Xu, She-Lei Feng, Wei Xue, and Zhen-Zhen Wang

*Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China

Abstract

Because heterogeneous catalysts have attracted great interest in organic chemistry, this paper reports facile β-cyclodextrin–SO3H–catalyzed cyclization to form imidazo[1,2-a]pyridin-3-amine derivatives via a three-component reaction. The main advantages of this strategy include short reaction time, practical simplicity, and high yield, and the catalyst can be separated easily by filtration and reused at least four times.

Supporting Info. (3.5MB)PDF (770KB)

Published online: 19th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13511
Two New Alkaloids from the Seeds of Cassia alata and Their Bioactivities

Pei-Song Yang, Wei Zhang, Xiao-Feng Shen, Xin-Lin Wang, Chao Li, Xiao-Wei Gong, Xu-Dong Zheng, Dong-Lai Zhu,* and Jia-Qiang Wang*

*School of Chemical Science and Technology, Yunnan University, Kunming 650091, China

Abstract

Two new alkaloids, 6-(hydroxymethyl)-3,9-dimethyl-7H-benzo[de]quinolin-7-one (1) and 6-(hydroxymethyl)-8-methoxy-3,9-dimethyl-7H-benzo[de]quinolin-7-one (2), together with four known alkaloids (3-6) were isolated from the seeds of Cassia alata. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-6 were tested for their anti-tobacco mosaic virus (TMV) activities, and the results showed that compound 2 exhibited high anti-TMV activity with inhibition rates of 38.5%. This rate is higher than that of the positive control. The cytotoxicities of compounds 1-6 against five human tumor cell lines (NB4, A549, SHSY5Y, PC3 and MCF7) were also tested. Compounds 1-6 showed weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 2.5-7.5 μM.

PDF (413KB)

Published online: 15th July, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13503
Facile Synthesis of Sulfonyl Amidines by 1,3-Dipolar Cycloaddition between 1-Morpholinocycloalkenes and Sulfonyl Azides without Catalyst

Chiaa Adiche, Mohammed Hamadouche, and Douniazad El Abed*

*Chemistry Department, Faculty of Exact and Applied Sciences, University of Oran 1, Ahmed BenBella, BP 1524 El M’naouar, Oran 31000, Algeria

Abstract

Three new series of sulfonyl amidines were prepared by 1,3-dipolar cycloaddition reaction between 1-morpholinocycloalkenes and various substituted sulfonyl azides without catalyst at room temperature. This reaction yielded unstable bicyclic Δ2-1,2,3-triazoline intermediates which rearranged themselves in situ into amidines by elimination of a nitrogen molecule. The reactions were performed under mild conditions and with moderate to good yields.

Supporting Info. (1.8MB)PDF (421KB)

Published online: 15th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13506
Lewis Acid-Catalyzed Borono-Minisci Reactions of Arylboronic Acids and Heterocycles

Joyce L. Biaco, Savannah L. Jones, and Timothy J. Barker*

*Department of Chemistry and Biochemistry, College of Charleston, 66 George St., Charleston, SC 29424, U.S.A.

Abstract

A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Brønsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.

PDF (396KB)

Published online: 13th July, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)9
Preparation and Biological Activity of Novel Twin-Drug Type C2-Symmetrical Cyclic Phenylboronic Acid Derivatives

Makoto Furutachi, Ayumi Ejima, Reika Tsuru, Saho Goto, Toshiaki Gondo, Kenta Ako, Saho Fuchigami, Saya Fujii, Arisa Okumura, Ayumi Tozuka, Kazumi Yokomizo, Jian-Rong Zhou, Hiroshi Inao, Yutaro Ono, Nobuhiro Kashige, Fumio Miake, and Kunihiro Sumoto*

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

Abstract

We here report the results of evaluation of antibacterial and anti-herpes simplex virus-1 (HSV-1) activities of a novel twin-drug type C2-symmetrical boronic acid and its pinacol ester derivatives. By using a primitive amide bond formation reaction, various targeted C2-symmetrical cyclic phenylboronic acid derivatives were obtained from the reactions of commercially available amino-substituted phenylboronic acid derivatives and diacid dichlorides. The C2-symmetrical bivalent molecule 3bd containing two cyclic phenylboronic acid pinacol ester moieties and a flexible hexamethylene linker showed both antibacterial activity (S. aureus) and anti-HSV-1 activity. The corresponding boronic acid derivative 3dd showed neither antibacterial nor anti-HSV-1 activity, indicating the importance of two pinacol ester functionalities.

PDF (355KB)

Published online: 12th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13510
KH2PO4 Promoted Practical and Environmentally Friendly Preparation of Coumarin-3-carboxylic Acids under Solvent-Free Condition

Shuangqiu Gao, Di Xiao, Ying Yang, Xiaoyü Wei, Sai Sun, Jian Lang, and Chengwei Lv*

*School of Chemistry and Chemical Engineering, Liaoning Normal University, No.850 Huanghe Road, Liaoning Province 116029, China

Abstract

An efficient and green protocol for synthesis of coumarin-3-carboxylic acids is developed in good to high yields via a Knoevenagel-intramolecular cyclization cascade reaction of Meldrum’s acid with various ortho-hydroxyarylaldehydes. This reaction is catalyzed by a combination of KH2PO4 (10 mol%) and water (100 μL). Solvent-free, cheap and eco-friendly catalyst, clean reaction conditions, simple workup procedure and easy isolation are the best features in this process.

Supporting Info. (539KB)PDF (325KB)

Published online: 11th July, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13484
An Efficient and Practical Preparation of a Potent Low-Affinity Na+-Dependent Glucose Cotransporter (SGLT2) Inhibitor, Sergliflozin Etabonate

Masahiro Kobayashi,* Hidetoshi Isawa, Junichi Sonehara, and Minoru Kubota

*Quality Assurance, Kissei Pharmaceutical Co., Ltd, 19-48 Yoshino, Matsumoto-City, Nagano-Pref., Japan

Abstract

The development of an efficient and practical process for the preparation of Sergliflozin etabonate (1), a prodrug of a novel selective low-affinity Na+-dependent glucose cotransporter (SGLT2) inhibitor, Sergliflozin (2), is described. Its development required a suitable process for large-scale manufacturing. We established a chromatography-free approach for 2-[(4-methoxyphenyl)methyl]phenol (5), the efficient O-glycosylation of 5 with penta-O-acetyl-β-D-glucopyranose (7) without using a trichloroimidate intermediate (9), and efficient reaction conditions to introduce an ethoxycarbonyl group onto the primary alcohol of 2 with high selectivity. This process provided 1 with a 45% overall yield from anisole (10).

PDF (508KB)

Published online: 7th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13501
Synthesis of Isoquinolinium via Rhodium(III)-Catalyzed Oxidative Annulation between Aldimines and Alkynes

Cheng-Qi Wang, Wei Zhang, Hui Lin, Fu Su,* and Lin Dong*

*West China School of Pharmacy, Sichuan University, 17# Third Section of South Renmin Road 610041, China

Abstract

Various isoquinolinium salts have been efficiently synthesized from aldehyde imines and alkynes via RhIII-catalyzed C–H activation and annulation reaction. A broad substrate scope has also been studied to provide various isoquinolinium triflate salts.

Supporting Info. (3.6MB)PDF (575KB)

Published online: 5th July, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13495
Skeletal Transformation of 2a,8b-Dihydrobenzo[b]cyclobute[d]pyran-3-ones into Dihydrodibenzofurans

Toru Tanaka, Masaki Nagahama, Navnath Dnyanoba Yadav, Hiroki Iwasaki, Minoru Ozeki, Naoto Kojima, and Masayuki Yamashita*

*Kyoto Pharmaceutical University, 5 Misasagi-Nakauchi, Yamashina, Kyoto, Japan

Abstract

Using dimethylsulfoxonium methylide as the methylene-transfer reagent, 8-methoxy-2a,8b-dihydrobenzo[b]cyclobute[d]pyran-3-ones were exclusively converted into the corresponding dihydrodibenzofuran derivatives. The use of a methoxy group as the substituent and its position are crucial to the success of this transformation.

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Published online: 30th June, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)4
Isolation and Evaluation of Hedgehog Inhibitors from Christmas Grass (Themeda arguens)

Tatsuro Yoneyama, Midori A. Arai,* Takashi Koyano, Thaworn Kowithayakorn, and Masami Ishibashi*

*Department of Natural Products Chemistry, Graduate School of Pharmaceutical Science, Chiba University, 1-8-1 Inohana, Chuo, Chiba, Japan

Abstract

The hedgehog (Hh) signaling pathway is an important regulator of embryonic development, tissue patterning, cellular proliferation and differentiation. However, aberrant activation of the pathway is associated with tumorigenesis. In this study, the Hh signal inhibitory activity of plant extracts was measured with a cell-based assay system that targets GLI1-mediated transcription. Activity guided analysis of MeOH extracts of christmas grass (Themeda arguens) led to the isolation of four inhibitory compounds: aciculatin (1), 7-de-O-methylaciculatin (2), 8-C-β-D-boivinopyranosylapigenin (3) and aciculatinone (4). Compound 1 strongly inhibited Hh/GLI1-mediated transcriptional activity with an IC50 value of 1.8 μM, and disrupted the formation of the GLI1-DNA complex by EMSA. 1 and 3 were cytotoxic for human prostate (DU-145) and breast (MCF-7) cancer cells. These compounds may serve as new tools for the molecular dissection of Hh pathway activation.

Supporting Info. (129KB)PDF (1.6MB)

Published online: 22nd June, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)5
Synthesis of (±)-Cephalanthrin A Using Baeyer-Villiger Oxidation

Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, and Minoru Ishikura*

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

Abstract

Indoloquinazoline alkaloid (±)-cephalanthrin A was synthesized through the Baeyer-Villiger oxidation of the phenyl ketone derived from aldol reaction of tryptanthrin and acetophenone.

PDF (360KB)

Published online: 9th June, 2016

Communication | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)1
A Water-Soluble Cavitand Sequesters 2-Nonenal, the Odor Component of the Elderly

Yang Yu, Simone Mosca, and Julius Rebek, Jr.*

*Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, U.S.A.

Abstract

Long chain aldehydes are principal components of odor in older populations. Here we show that a synthetic container molecule, a deep water-soluble cavitand forms complexes in aqueous (D2O) solution. The cavitands bind the aldehyde in a compressed conformation that reduces exposure to the medium. The aldehyde is extracted from the complex by tetrachloroethane and sodium dodecyl sulfate, chemical agents of dry cleaning or laundering, respectively. The large-scale synthesis of the cavitand opens possibilities for its attachment to clothing fibers.

PDF (252KB)

Published online: 7th June, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)3
Synthesis of 3-Bromoquinoline-2(1H)-thiones and 2-(Alkylsulfanyl)-3-bromoquinolines Based on the Reaction of 2-(2,2-Dibromoethenyl)phenyl Isothiocayanates with Butyllithium

Kazuhiro Kobayashi,* Ippei Nozawa, and Takashi Nogi

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

The synthesis of 3-bromoquinoline-2(1H)-thiones and 2-(alkylsulfanyl)-3-bromoquinolines from readily available starting materials was accomplished. Thus, 2-(2,2-dibromoethenyl)phenyl isothiocyanates were treated with butyllithium to afford, after aqueous workup, 3-bromoquinoline-2(1H)-thiones. When haloalkanes were added prior to workup, 2-(alkylsulfanyl)-3-bromoquinolines were obtained. An elaboration of one of these compounds to a thieno[2,3-b]quinoline derivative and one-pot preparation of 3-substituted quinoline-2(1H)-thiones were also achieved.

PDF (352KB)

Published online: 2nd June, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-16-S(S)2
Synthetic Study towards Construction of Potential Scaffold of Antitumor Agents Andrastins

Shuqiang Yin, Kenji Sugimoto, Hideo Nemoto, and Yuji Matsuya*

*Graduate School of Medicine and Pharmaceutical Sciences for Research, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan

Abstract

For a construction of potential scaffold of antitumor agents andrastins, intramolecular Diels-Alder reaction of the triene composed of trans-fused AB ring with tethered D ring was examined. The reaction in refluxing toluene afforded a desired cis-fused hydrindane skeleton, the relative stereochemistries of which were unambiguously determined by X-ray crystallographic analysis.

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Published online: 28th March, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)18
Synthesis of Phenantroline and Indole Based Hybrid Cyclophane Derivatives via Ring-closing Metathesis

Sambasivarao Kotha,* Mukesh E. Shirbhate, Ajay Kumar Chinnam, and Gaddameedi Sreevani

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India

Abstract

Here, we report new phenanthroline-based cyclophane derivatives via Fischer indolization and ring-closing metathesis (RCM) as key steps. Grignard addition of 2 and subsequent autoxidation gave the phenanthroline dione derivative 3. Further, Fischer indolization of 3 followed by RCM under mild reaction conditions gave indole and phenanthroline containing hybrid cyclophanes such as 6a and 6b.

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Published online: 1st February, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)48
Synthetic Studies toward Concavine: Synthesis of The BCD Ring Syste

Yosuke Komori, Akitoshi Kozen, and Masahiro Toyota*

*Team TOYOTA, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuencho, Sakai, Osaka 593-8531, Japan

Abstract

The BCD ring system of concavine is realized stereoselectively using a palladium-catalyzed cycloalkenylation to synthesize the CD ring and an intramolecular aza-Michael reaction to append the third ring.

PDF (996KB)

Published online: 12th January, 2016

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)26
Antiproliferative Activity of Hybrid Compounds Between 6-Methoxy-3-(4-Methoxyphenyl)-1H-Indole and 3-Phenylpiperidine Against HCT-116 and HL-60 Cells

Noriyuki Hatae,* Takashi Nishiyama, Shoko Tamura, Ryohei Yamamoto, Ayaka Matsui, Hiroki Shinchi, Satoshi Hibino, Chiaki Okada, Teruki Yoshimura, Tominari Choshi, and Eiko Toyota*

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

Abstract

Indole derivatives have been potential anticancer drugs. Methyl 6-methoxy-3-(4-methoxyphenyl)-1H-indole-2-carboxylate, in particular, was reported as a potent antiproliferative agent against MCF-7, NCI-H460, and A375-C5 tumor cells. In this study, the 3-arylindole-2-carboxylate exhibited weak activity against HCT-116 colon tumor and HL-60 promyelocytic leukemia cells. To develop the potent antiproliferative indole derivatives against HCT-116 and HL-60 cells, we synthesized 6-methoxy-3-(4-methoxyphenyl)-1H-indoles with various 2-substituents and assessed their activity. The 4-phenylpiperidine derivatives attenuated the tumor cells viability. Furthermore, their calculated structure resembled that of the antiproliferative loperamide derivatives.

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