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15 data found. 1 - 15 listed

Published online: 27th August, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13293
Design, Synthesis, and Evaluation of Novel 2-Halogenated or Aminated Carbocyclic Oxetanocin a Analogs as Potential Angiogenic Agents

Norikazu Sakakibara,* Junsuke Igarashi, Maki Takata, Ryoji Konishi, Natsuki Suzue, Yoshihisa Kato, Tokumi Maruyama, and Ikuko Tsukamoto

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

Abstract

We succeeded in the synthesis of four types of carbocyclic oxetanocin A (2-Chloro-C.OXT-A; COA-Cl) analog: 2-halogenated or aminated carbocyclic oxetanocin A: COA-F, COA-Br, COA-I, and COA-NH2, which were synthesized and evaluated using human umbilical vein endothelial cells. Among these compounds, 100 M COA-Br and COA-I had greater angiogenic activity, with relative tube areas of 2.10 0.32 and 2.01 0.61 (mean SD), respectively, which were comparable to that of COA-Cl (2.30 0.59).

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Published online: 24th August, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13256
Metal-Free Synthesis of Benzothiazoles from Disulfides of 2-Aminobenzenethiol and Carboxylic Acid via PCl3-Promoted Tandem Reaction

Guangyan Du, Ning Zhu,* Limin Han, Hailong Hong, and Quanling Suo

*Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051, China

Abstract

A metal-free process for the synthesis of benzothiazoles via PCl3-promoted cleavage/acylation/ cyclization of disulfides and carboxylic acids has been developed. In addition to acting as the acylating reagent which converted carboxylic acids into acyl chlorides, PCl3 also converted disulfides to thiols, which promoted disulfides of 2-aminobenzenethiol reacted with carboxylic acid to produce benzothiazoles. The developed method is applicable to a wide range of carboxylic acids containing different functional groups.

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Published online: 24th August, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)5
Total Synthesis of Carbazole-1,4-quinone Alkaloid Koeniginequinones A and B based on a One-Pot Cyclocarbonylation Procedure from 2-Alkenyl-3-iodoiodoindole

Takashi Nishiyama, Nanase Satsuki, Satoshi Hibino,* Mami Fujii, Takumi Abe, Minoru Ishikura, and Tominari Choshi*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

Total syntheses of koeniginequinones A and B, isolated from Murraya koenigii, were newly achieved by constructing of carbazole-1,4-quinone using a one-pot Pd-catalyzed cyclocarbonylation method with 2-(but-2-en-1-yl)-3-iodoindoles derived from known methyl 6-methoxyindole-2-carboxylate and methyl 5,6-dimethoxyindole-2-carboxylate, followed by desilylation, and an oxidation sequence.

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Published online: 24th August, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13290
Synthesis and Antihypertensive α-Blocking Activity Evaluation of Thiazole Derivatives Bearing Pyrazole Moiety

Sobhi Gomha,* Khaled Khalil, Hassan Abdel-aziz, and Mohamed Abdalla

*Department of Organic Chemistry, Cairo University, Giza-Haram 12613, Egypt

Abstract

A novel, facile reaction for the synthesis of series of thiazole derivatives has been developed from the reaction of the appropriate thiosemicarbazone derivatives and 2-bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone in ethanol under reflux. The structures of the newly synthesized products were established on the basis of spectral data (mass, IR, 1H and 13C NMR) and elemental analyses. The pharmacological screening showed that many of the synthesized compounds exhibit a good antihypertensive α-blocking activity and having low toxicity, as compared to Minoxidil.

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Published online: 21st August, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13286
The Synthetic Studies of Carbazole Alkaloids

Hajime Yokoyama,* Yuzen Shoji, Takayoshi Kubo, Masahiro Miyazawa, and Yoshiro Hirai

*Department of Chemistry, Graduate School of Science and Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan

Abstract

The carbazole alkaloids have profound biological activities and material properties. We reported that 3, 4-substituted, 3-substituted and 4-substituted carbazoles were regioselectively synthesized from indoline derivatives by means of Diels-Alder reaction in the presence or absence of Pd catalyst and attained the synthesis of natural carbazole alkaloid from 3-substituted carbazole, too.

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Published online: 11th August, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13270
Synthesis and Characterization of Polysubstituted 5-Quinolinecarbaldehyde Derivatives

Nguyen Huu Dinh,* Duong Quoc Hoan, Nguyen Hien, and Tran Thi Thu Trang

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

Abstract

A new quinolinecarbaldehyde, 7-(carboxymethoxy)-6-hydroxy-3-sulfo- quinoline-5-carbaldehyde (1), was synthesized from eugenol, a natural phenol, by four successive reaction steps. The condensation of 1 with various amino compounds afforded 12 Schiff-bases (213) and 3 hydrazones (1416). The structures of the aldehyde, its Schiff-bases and the hydrazone derivatives were determined by analyzing their IR, 1D NMR, 2D NMR and MS spectra. 1H NMR and NOESY data show that the imine -CH=N- group in the reported Schiff-bases and hydrazones exists in E-configuration.

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Published online: 11th August, 2015

Communication | Regular issue | Prepress
DOI: 10.3987/COM-15-13288
Synthesis of the Aglycon of Pentalinonside

Nobuhisa Isaka, Saki Kawada, Masaji Ishiguro,* and Minoru Tamiya*

*Chemical Biology Laboratory, Department of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Niigata 956-8603, Japan

Abstract

The aglycon of pentalinonside (2), a novel seco-pregnane with cage-like DEF-rings, was synthesized. Polyoxygenated DEF-rings were constructed using a known 14,20(16),21(15)-triol derivative via 5-exo-cyclization for the F-ring annulation, followed by C14–21(15) oxidative cleavage and intramolecular acetalization.

Supporting Info. (357KB)PDF (620KB)

Published online: 6th August, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13267
Regioselective Synthesis of Pyrazoles and Pyrazolo[1,5-a]Pyrimidines: Structural Characterization by HMBC NMR

Abdullah S. Al-Bogami and Tamer S. Saleh*

*Department of Green Chemistry, National Research Centre, El-Tahrir Street, Dokki, Giza 12622, Egypt

Abstract

In this study a series of novel pyrazoles and pyrazolo[1,5-a]pyrimidines with a sulfone moiety incorporated the coumarin ring were efficiently synthesized. These pyrazoles and pyrazolo[1,5-a]pyrimidines were synthesized by treating enaminone derivative of β-ketosulfone (3-(2-tosylacetyl)-2H-coumarin) with substituted hydrazines and 5-aminopyrazole derivatives, respectively under microwave irradiation. The structures of the products thus obtained were characterized by 2D NMR (HMBC).

Supporting Info. (1.3MB)PDF (824KB)

Published online: 6th August, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13282
Synthesis and in vitro Cytotoxicity Evaluation of New 2-Thioxo-benzo[g]quinazolin-4(3H)-one Derivatives

Rashad Al-Salahi,* Rabab A. El Dib, and Mohamed Marzouk*

*Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh-11451, Saudi Arabia

Abstract

Preparation of the titled 2-thioxo-benzo[g]quinazolin-4(3H)-ones (1–4) has been previously reported. In the present study, compounds (1–4) were elaborated in high and quantitative yields by simple modification on the reported synthetic route. Treatment of 2-thioxo-benzo[g]quinazolin-4(3H)-ones (1–4) with hydrazine hydrate or with different alkyl(heteroalkyl) halides afforded smoothly the target products 5, 6 or 7–28 in good and high yields. The in vitro cytotoxicity of compounds 1–28 was evaluated against colon HCT-116, hepatocellular Hep-G2, and breast MCF-7, prostate PC-3 and lung A-549 cancer cell lines, using MTT assay. The IC50-values of the target compounds are recorded in µg/mL and doxorubicin used as a reference drug. The results revealed that compounds 1, 3, 7, 10, 13, 14, 15, 16, 20, 21 and 22 had significant cytotoxic effects in relation to the reference drug. The structures of compounds 1–28 were elucidated by means of 1H- and 13C-NMR and HREI mass spectrometry.

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Published online: 5th August, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)4
Synthesis of Benzophenone and Phenylazide Derivatives of Salicin for Functional Analysis of the Bitter Taste Receptor Using Photoaffinity Labeling

Takuma Yoshida, Yasuyuki Hashidoko, and Makoto Hashimoto*

*Division of Applied Science, Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan

Abstract

Salicin is a substance that is well known for its bitter taste. Photoreactive benzophenone and phenylazide derivatives of salicin are for the functional analysis of interactions between the bitter taste receptor and salicin. First synthesis of these derivatives was prepared from acetobromo-α-D-glucose via glucosidation with salicylaldehyde derivatives followed by reduction of aldehyde to form salicin skeleton.

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Published online: 4th August, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13266
Phenylpropanoids from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activities

Qin-Peng Shen, Lan Li, Xin-Meg Xu, Chun-Bo Liu, Neng-Jun Xiang, Feng-Mei Zhang, Pei He, Zhi-Hua Liu, Shan-Zhai Shang, Ming-Ming Miao,* and Guang-Yu Yang*

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

Abstract

Two new phenylpropanoids, 5-hydroxy-6-(3-hydroxypropanoyl)- isobenzofuran-1(3H)-one (1), 6-(3-hydroxypropanoyl)-5-methylisobenzofuran- 1(3H)-one (2), together with four known phenylpropanoids (3-6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-5 were tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that Compound 2 showed high anti-TMV activity with inhibition rate of 29.2%. This rate is close to that of positive control. The other compounds also showed potential anti-TMV activity with inhibition rates in the ranges of 20.3-24.6%, respectively.

Supporting Info. (100KB)PDF (704KB)

Published online: 4th August, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13285
Viridobrunnines A and B, Antimicrobial Phenoxazinone Alkaloids from A Soil Associated Streptomyces sp.

Xiu Mei Zhang, Xu Liu, Zhe Wang, Zhen Hua Tian, and Wei Dong Xie*

*Department of Pharmacy, Marine College, Shangdong University at Weihai, Wenhua Xilu 180, Weihai 264209, China

Abstract

Chemical investigation of a Streptomyces sp. strain designated A1302 isolated from soil sample led to the discovery of two new phenoxazinone alkaloids, viridobrunnines A and B (1 - 2), along with two known analogues exfoliazone (3) and chandrananimycin D (4). Their structures were established by means of spectroscopic methods. The antibacterial and antifungal activity of isolated compounds was assayed. Viridobrunnine B (2) exhibited potent antibacterial activity against Bacillus subtilis with inhibition zone from 13 mm to 15 mm.

Supporting Info. (1.6MB)PDF (530KB)

Published online: 24th July, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)3
Synthesis of 2-Arylquinoxalines: Triarylstibane-Catalyzed Oxidative Cyclization of α-Hydroxy Ketones with 1,2-Diamines Under Aerobic Conditions

Mio Matsumura, Rie Takada, Yuu Ukai, Mizuki Yamada, Yuki Murata, Naoki Kakusawa, and Shuji Yasuike*

*Faculty of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho Chikusa-ku Nagoya city 464-8650, Japan

Abstract

The reaction of -hydroxy ketones with 1,2-diamines in the presence of triphenylstibane (10 mol%) as catalyst led to the formation of 2-arylquinoxalines in moderate to good yield under aerobic conditions. This reaction is the first example of oxidative cyclization catalyzed by organoantimony compounds.

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Published online: 15th July, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)2
Synthesis of 3,4-Dihydro-2H-1,3-benzoxazine-2-thiones via Cyclization of 2-(1-Isothiocyanatoalkyl)phenols

Kazuhiro Kobayashi,* Hiroki Inouchi, Naoki Matsumoto, 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

Convenient sequences for the preparation of 3,4-dihydro-2H-1,3-benzoxazine-2-thiones from 2-hydroxybenzaldehyde and 2-hydroxyphenyl ketones or 2-methylphenols have been developed, which both employ cyclization of 2-(1-isothiocyanatoalkyl)phenols generated in situ under mild conditions.

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Published online: 10th June, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)1
Crystal Structures of N,N’-bis(5-Dodecyloxytropon-2-yl)piperazine and N,N’-bis(4-Butoxyphenyl)piperazine

Kanji Kubo,* Emi Yamamoto, Taisuke Matsumoto, Seiji Ujiie, and Akira Mori

*Department of Life Science and Technology, Faculty of Engineering, Hokkai-Gakuen Univiersity, Sapporo, Hokkaido 062-8605, Japan

Abstract

The crystal structures of N,N’-bis(5-dodecyloxytropon-2-yl)piperazine (1) and N,N’-bis(4-butoxyphenyl)piperazine (2) were analyzed by X-ray crystallography. The molecules of 1 and 2 sits on a center of symmetry such that the two aromatic rings are in an anti conformation with respect to one another across the piperazine ring. The molecules (1, 2) forms a tilted layer structure via intermolecular C-H∙∙∙O and C-H∙∙∙π interactions in 1 and intermolecular C-H∙∙∙O, C-H∙∙∙N, and C-H∙∙∙π interactions in 2.

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15 data found. 1 - 15 listed