Regular & Special Issues

8 data found. 1 - 8 listed

Published online: 27th February, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13184
Synthesis of New Hydantoins Bearing Glutarimide or Succinimide Moiety and Their Evaluation for Cell-Differentiation-inducing and Anti-Angiogenic Activities

Jun-ichi Yamaguchi,* Tomomi Noguchi-Yachide, Yuka Sakaguchi, Chiaki Shibata, Shinnosuke Kanuma, Akiko Yoshizaki, Yuka Takizawa, and Yuichi Hashimoto

*Department of Applied Chemistry, Faculty of Engineering, Kanagawa Institute of Technology, Shimo-ogino, Atsugi-shi 243-02, Japan


Several derivatives of hydantoin containing glutarimide or succinimide at the 3-position were synthesized. The new hydantoin derivatives had a structure similar to that of thalidomide, and so may possess activity similar to that of thalidomide and/or its analogs, such as effects on cell differentiation and angiogenesis. Some hydantoins showed enhancing effects on all-trans retinoic acid (ATRA)-induced cell differentiation of human leukemia cell line HL-60 and anti-angiogenic activity on human umbilical vein endothelial cells (HUVEC). These new hydantoin derivatives were more effective than thalidomide in cell differentiation-inducing activity on HL-60 and anti-angiogenic activity on HUVEC.

Supporting Info. (5.6MB)PDF (825KB)

Published online: 26th February, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-14-13126
Domino [3+2+1] Heteroannulation for Stereoselective Synthesis of Anti-Pyrazolo[3,4-d][1,3]oxazines

Yi Ning, Wei Fan, Wen-Juan Hao, Mu-Yan Sun, Bo Jiang,* Shu-Jiang Tu,* and Guigen Li*

*Department of Chemistry & Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, U.S.A.


A novel three-component domino reaction of arylglyoxals with pyrazol-5-amines in HOAc has been developed, providing an efficient and stereoselective access to polysubstituted anti-pyrazolo[3,4-d][1,3]oxazines in a intermolecular manner. Features of this strategy include mild conditions, convenient one-pot operation, and excellent stereoselectivity, which make highly attractive.

Supporting Info. (771KB)PDF (644KB)

Published online: 25th February, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13181
Synthesis and Antibacterial Activity of Novel N-Carboxyalkyl-N-phenyl-2-aminothia(oxa)zole Derivatives

Rita Vaickelioniene, Kristina Mickeviciene, Kazimieras Anusevicius, Jurate Siugzdaite, Kristina Kantminienė, and Vytautas Mickevicius*

*Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, Kaunas LT-50254, Lithuania


N-Phenyl-N-thiocarbamoyl-α- and β-methyl-β-alanines were converted into a series of 1,3-thiazole derivatives by treatment with chloroacetaldehyde and haloketones. The reaction of N-phenyl-N-thiocarbamoyl-β-alanines and N-carbamoyl-N-phenyl-β-alanines with 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloroquinoxaline provided naphthoquinone- and quinoxaline-fused thiazoles and oxazoles, respectively. A number of the synthesized compounds exhibited good antibacterial activity against Staphylococcus aureus and Salmonella enteritidis with MIC and MBC values (62.5 and 125 µg/mL, respectively) which are the same or even lower than those for the antibiotic oxytetracycline.

PDF (350KB)

Published online: 24th February, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13166
Convenient Synthesis of Novel Phenylpyrimido[1,2-c]thienopyrimidinones as IL-6/STAT3 Inhibitors

Jae Hoo Park, So Young Hong, Jungah Kim, Hyuck Joo Lee, Hyun Ho Lee, Ka Young Kim, Seung Woong Lee, Hyun-Mee Oh, Mun-Chul Rho, Beom-Gyu Lee, and Yang-Heon Song*

*Department of Chemistry, Mokwon University, Daejeon, Doan-dong 800, 302-729, Korea


New phenylpyrimido[1,2-c]thienopyrimidinones 4A and 4B were easily prepared in good yields by the one-pot reaction of formamidine derivatives 2 of 4-aminothienopyrimidine 1 with phenylacetyl chlorides. The application of this convenient and reliable method could be used for the synthesis of a variety of pyrimido[1,2-c]thienopyrimidinone derivatives of biological importance. Some of the compounds synthesized showed strong IL-6/STAT3 inhibition.

PDF (399KB)

Published online: 24th February, 2015

Review | Regular issue | Prepress
DOI: 10.3987/REV-15-818
Transition Metal-Catalyzed Intramolecular Cyclization of Propargyl Alcohols and Their Derivatives for the Synthesis of Highly Substituted Five-Membered Oxygen Heterocycles

Masahiro Egi* and Shuji Akai*

*Synthetic Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan


The transition metal-catalyzed intramolecular cyclization of propargyl alcohols and their derivatives has been widely utilized in the synthesis of five-membered oxygen heterocycles such as furans, hydrofurans, and furanones. Prerequisites for the efficient transformations into highly substituted target compounds include the regioselectivity of the cyclization step and the chemoselectivity of the transition metal-mediated activation of substrates. This review documents recent progress on the title reactions by categorizing the initial activation modes of substrates.

PDF (902KB)

Published online: 20th February, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-14-13160
Reactivity of 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)-2-nitrosoacetonitrile: A Facile One-Pot Synthesis of Benzimidazo[1,2-a]piperazine Derivatives

Samia M. Sayed, Mohamed A. Khalil, and Mohamed A. Raslan*

*Department of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt


Several new heterocyclic compounds such as benzimidazo[1,2-a]piperazine derivatives (5-7;9,10 and 14,15,17) have been synthesized by the reactions of the versatile 2-(1-methyl-1H-benzo[d]imidazol-2-yl)-2-nitroso-acetonitrile (2) with malononitrile derivatives (3a-e) and 2-cyanomethyl-benzimidazole derivatives (1b,c). Oxidation of iminopyrazino[1,2-a]benzimidazole-3-carbothioamide derivatives 9 via refluxing in aqueous H2O2 solution afforded iminopyrazino[1,2-a]benzimidazole-3-carboamide derivatives 10. Also, reaction of 9 with 1-aryl-2-bromoethanone derivatives (11a,b) in refluxing DMF, the Hantzsch-type thiazoles (12a,b) were obtained. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis.

PDF (290KB)

Published online: 17th February, 2015

Review | Regular issue | Prepress
DOI: 10.3987/REV-14-812
Chemistry of Macrocyclic β-Lactam: An Overveiw

Vijaya Bhaskar Vangala, Mahagundappa Rachappa Maddani, Rama Mohan Hindupur, and Hari Narayan Pati*

*Department of Chemistry, Advinus Therapeutics Ltd., 21 and 22 Peenya Industrial Area, 560058, India


β-Lactam macrocycles displayed major contributions in the filed of drug discovery. The chemical potentiality of β-lactam has proved their usefulness in the discovery of variety of conformationally restricted macrocycles. Macrocycles containing versatile functionalities derived from β-lactam have also been employed in the fields of supramolecular chemistry. In this review, attempts were made to summarize the recent methods for synthesis of potential β-lactam containing macrocycles.

PDF (361KB)

Published online: 10th February, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13171
Synthesis and Applications of a New Epoxy-isoindolinone

Shang-Shing P. Chou* and Sung-Lin Hsu

*Department of Chemistry, Fu Jen Catholic University, 510 Chung-Cheng Rd., Hsin-Chuang, New Taipei City 24205, Taiwan, R.O.C.


A new epoxy-isoindolinone was stereoselectively synthesized, and its reactions gave several interesting products including a new 6-azabicyclo[3.2.1]octane derivative.

PDF (560KB)
8 data found. 1 - 8 listed