Regular Issues

8 data found. 1 - 8 listed

Published online: 15th August, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14134
Synthesis and Antioxidant Activities of Some Novel Indane-Amide Substituted Pyrazole, Pyrimidine, Pyridine and 2-Pyrone Derivatives

Khaled S. Mohamed* and Elsherbiny H. El-Sayed

*Engineering Chemistry Department, Higher Institute for Engineering and Technology, New Damietta, New Damietta 34518, Egypt


2-Cyano-N-(2,3-dihydro-1H-5-indenyl)-3-(dimethylamino)acrylamide (3) was used in synthetic paths to some novel indane-amide containing pyrazole, pyrimidine, fused pyrimidines, fused pyridines and 2-pyrone derivatives by reaction of 3 with various reagents. The newly synthesized compounds were investigated for their antioxidant activity. Some of the tested compounds exposed auspicious activities.


Published online: 13th August, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14128
Synthesis and the First Structure–Activity Relationship Study of Imidazole Alkaloid from Red Ascidian as Aldose Reductase Inhibitors

Kenta Morikawa, Sota Uno, Shoko Higashi, Masaru Goto, and Ryota Saito*

*Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan


We synthesized a series of 2-aroyl-4-aryl-1H-imidazoles (2 and 3) and evaluated their in vitro AR inhibitory activity for the first time. We observed improved activities with derivatives having multiple catechol moieties.


Published online: 13th August, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14129
Ruthenium-Catalyzed Hydroxyethylation of Cyclic Amines with Ethylene Glycol

Yushi Nakamura, Shuhei Tomioka, Yohei Oe,* and Tetsuo Ohta

*Department of Biomedical Information, Faculty of Life and Medical Sciences, Doshisha University, 1-3 Tatara-miyakodani, Kyotanabe, Kyoto 610-0394, Japan


It was found that a catalyst system RuCl2(PPh3)3/Xantphos is effective to install hydroxyethyl groups to the nitrogen atom of cyclic amines. Thus, the reactions of cyclic amines with ethylene glycol were performed in the presence of the RuCl2(PPh3)3/Xantphos catalyst in toluene at 120 °C for 22 h to provide the corresponding β-amino alcohols in up to 92% yield.

FREE:Supporting Info. (828KB)PDF (727KB)

Published online: 7th August, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14110
Synthesis and Biological Evaluation of 3-((1-Methyl-1H-pyrrol-2-yl)methylene)indolin-2-one Derivatives as Potent Anticancer Active Agents

Jie Chen, Wei-nan Hu, Yang Xu, Wen Li, Ya-yun Qi, Yi-hong Fu, Jia-min Liu, Zhen-chao Wang,* and Gui-ping Ouyang*

*College of Pharmacy, Guizhou University, Huaxi St., Guiyang 550025, China


A series of 3-((1-methyl-1H-pyrrol-2-yl)methylene)indolin-2-one derivatives were designed, synthesized, and evaluated for their inhibition activities against four tumor cells in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Antitumor experiments indicated that some compounds exhibited significant inhibition activities against SMMC-7721. Especially, the IC50 values of 7k and 7l (IC50 = 8.08 ± 0.95 µM, IC50 = 3.01 ± 0.61 µM) demonstrated the best antitumor activities against SMMC-7721 (human hepatoma cell lines) than the positive agents Sunitinib (IC50 = 8.27 ± 0.40 µM). Likewise, their structure activity relationship (SAR) was studied.

FREE:Supporting Info. (4MB)PDF (600KB)

Published online: 7th August, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14127
Synthesis of 8-Oxa-2-azabicyclo[3.2.1]octane Using a 1,3-Dipolar Cycloaddition Reaction

Kazuhiro Higuchi,* Yoshiki Matsubayashi, Takuma Sakurai, Motoki Ito, and Shigeo Sugiyama

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


Herein, we report the application of 1,3-dipolar cycloaddition reaction toward the synthesis of a variety of 8-oxa-2-azabicyclo[3.2.1]octane compounds, the core structure of atkamine. The target compounds were obtained using a combination of a vinyl ether and carbonylylide, which was generated from a diazo compound and rhodium catalyst, in the presence of a Lewis acid.


Published online: 30th July, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14114
Enviromentally Friendly Synthesis of N-Methylated Nitrogen Heterocycles from an Aqueous Solution of Methylamine and Diols

Akane Enomoto, Takuya Shimbayashi, and Ken-ichi Fujita*

*Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan


N-Methylated nitrogen heterocycles are important compounds which are very common in organic, pharmaceutical, and material chemistry. Development of new environmentally friendly catalytic methods for the synthesis of N-methylated heterocycles using cost-effective and readily-available starting materials is strongly demanded. Herein, we report the efficient synthesis of N-methylated heterocycles using readily-available aqueous solution of methylamine and various diols catalyzed by iridium complexes. This catalytic system is attractive because of its high atom economy exhausting water as a sole by-product.

FREE:Supporting Info. (1.2MB)PDF (641KB)

Published online: 17th July, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14112
Synthesis of Optically Acitve γ-Lactams by Palladium Catalyzed Asymmetric Dicarbonylation Reaction of N-Arylsufonyl Homoallylic Amines

Ryosuke Takahashi, Nga Hang Thi Phan, Takuya Suga, Takahiro Soeta, and Yutaka Ukaji*

*Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan


Optically active γ-lactams were prepared by asymmetric dicarbonylation reaction of N-arylsulfonyl homoallylic amines catalyzed by palladium in the presence of copper(I) triflate. By the use of benzyl-substituted bioxazoline ligand, the corresponding γ-lactams were obtained with enantioselectivities of up to 67% ee.

FREE:Supporting Info. (239KB)PDF (255KB)

Published online: 12th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14033
Synthesis of 1,2-Benzothiazole-3(2H)-thione 1,1-Dioxides by DBU-Promoted Cyclization of 2-(Aminosulfonyl)-N-methylbenzothioamide Derivatives

Kazuhiro Kobayashi* and Daiki Fujiwara

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


An efficient method for the preparation of 2-alkyl-1,2-benzothiazole-3(2H)-thione 1,1-dioxides has been developed. Thus, the reaction of 2,N-dilithio derivatives of N-alkylbenzenesulfonamides with methyl isothiocyanate affords 2-[(alkylamino)sulfonyl]-N-methylbenzothioamides, which are treated with a catalytic amount of DBU in refluxing toluene to provide the desired products in moderate to good yields.

8 data found. 1 - 8 listed