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Published online: 5th February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13368
Facile and Efficient Synthesis of 2-Aminoquinoline Derivatives Reduced by Zn/AcOH

Guolan Dou,* Deming Wang, and Daqing Shi

*School of Safety Engineering, China University of Mining & Technology, Xuzhou 221116, China

Abstract

In this paper, a simple and efficient method for one-pot synthesis of 2-aminoquinolines was accomplished in good yields via reductive cyclization of nitro and cyano groups mediated by zinc/acetic acid is reported.

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Published online: 5th February, 2016

Communication | Regular issue | Prepress
DOI: 10.3987/COM-15-13371
Catalytic Cyclization of 2,3-Dibromopropionates with Benzyl Azides to Afford 1-Benzyl-1,2,3-triazole-4-carboxylate: The Use of a Nontoxic Bismuth Catalyst

Hong-bin Sun,* Dong Li, Weiping Xie, and Xinlin Deng

*Department of Chemistry, Northeastern University of China, Wenhua Road 3-11, Shenyang 110819, China

Abstract

We synthesized 1,2,3-triazoles via the cyclization of 2,3-dibromopropionates with benzyl azides. Bismuth chloride is an efficient catalyst, and the reaction is accelerated by weak bases such as sodium acetate. A variety of functional groups are compatible with this catalytic protocol, and it takes advantage of oxygen stable catalyst and substrates because the reactive dibromides are saturated.

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Published online: 5th February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13372
Ring-Opening Reactions of Aziridines with Carboxylic Acids Catalyzed by DBU

Yanqin Guo, Yepeng Xie, Qin Yang, Songsong Xu, Zhihong Deng, Xuechun Mao, and Yiyuan Peng*

*College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China

Abstract

An efficient ring-opening of aziridines with various carboxylic acids catalyzed by an organocatalyst—DBU afforded the corresponding products in good to excellent yield under mild reaction conditions.

PDF (555KB)

Published online: 4th February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13342
Synthesis and Biological Evaluation of Novel Coumarin Derivatives as Antiplatelet Agents

Peng Huang, Lei-Lei Gao, Zhuo Zhang, Jing-Ru Liu, and Li-Qin He*

*School of Pharmacy, Anhui University of Chinese Medicine, Yaohai District of Hefei City, Anhui Province, Mo Dian Xiang Anhui University of Chinese medicine shaoquan Lake Campus, 230012, China

Abstract

In order to develop anti-thrombotic agents with higher potency, a series of novel coumarin derivatives (5a-m) were designed, synthesized and biologically evaluated. Compound 5e displayed the strongest activity in inhibiting the adenosine diphosphate (ADP)-induced platelet aggregation in vitro, with 2.3-fold more effectiveness than clinically used antiplatelet drug aspirin (ASP). Thus, Compound 5e could deserve further investigations as antiplatelet agents.

Supporting Info. (536KB)PDF (488KB)

Published online: 4th February, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13394
Inter- and Intramolecular Diels-Alder Reaction of Ethenetricarboxylate Derivatives

Shoko Yamazaki,* Hirotaka Sugiura, Mamiko Niina, Yuji Mikata, and Akiya Ogawa

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

Abstract

Inter- and intramolecular [4+2] cycloaddition reactions of highly electron-deficient ethenetricarboxylates have been studied. Intermolecular Diels-Alder reaction of ethenetricarboxylate esters and cyclopentadiene proceeded at room temperature or -20 °C to give cycloadducts with 1:1.5-1.9 endo:exo ratio. Lewis acids such as EtAlCl2, Zn(OTf)2 and Cu(OTf)2 catalyzed reaction at room temperature or -40 °C gave cycloadducts with 3.1-5.4:1 endo:exo ratio. Reaction of N-benzyl- or N-allyl-2-furylmethylamine and 1,1-diethyl 2-hydrogen ethenetricarboxylate in the presence of EDCI/HOBt/Et3N at room temperature led directly to an intramolecular Diels-Alder adduct stereoselectively. The observed stereoselectivities were explained by the use of DFT calculations.

Supporting Info. (10.4MB)PDF (762KB)

Published online: 4th February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13398
Room-Temperature One-Pot Palladium-Catalyzed Synthesis of 3-Hydroxyisoindolin-1-ones from Phenylglyoxylic Acids

Menglei Yuan, Yu Sun, Hui Yan, Jinxiong Wu, Gaofeng Ma, Feng Li, Siyu Miao, Mengyao Hao, and Na Li*

*Department of Chemical Engineering & Process, North University of China, Changning Road 65, Shuozhou, Shanxi, 036000, China

Abstract

A room-temperature and efficient synthesis of 3-hydroxyisoindolin-1-ones by Pd-catalyzed C-H activation has been proposed. Wide ranges of benzamides and phenylglyoxylic acids indicated good functional group tolerance and wide potential application of this approach. Moreover, good yields of products further made it practical and attractive.

Supporting Info. (3.3MB)PDF (471KB)

Published online: 2nd February, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13387
An Efficient and Convenient Synthesis of Acyl CoA: Monoacylglycerol Acyltransferase 2 Inhibitor, 2-[2-(4-tert-Butylphenyl)ethyl]-N-[4-(3-cyclopentylpropyl)-2-fluorophenyl]-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide

Tsuyoshi Busujima* and Hiroaki Tanaka

*Medicinal Chemistry 3, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-cho Kita-ku Saitama 331-9530, Japan

Abstract

An efficient and convenient synthesis of MGAT2 inhibitor, 2-[2-(4-tert-butylphenyl)ethyl]-N-[4-(3-cyclopentylpropyl)-2-fluorophenyl]-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide (1), is reported. The optimized route consists of an effective chlorosulfonylation and debromination, resulting in an increase in the total yield from 6.8% to 45%, compared with our previous method. This synthetic approach enabled the synthesis of 1 to be scaled-up to a multi-gram scale.

PDF (890KB)

Published online: 2nd February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13397
Synthesis of Novel Benzofuro-Fused Thiazolo[3,2-a]pyrimidinones via Pictet-Spengler Reaction

Dao-Lin Wang,* Dong Wang, Jian-Hua Qiang, and Lin Liu

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

Abstract

An efficient method for the preparation of novel benzofuro[3’,2’:2,3]pyrido[4,5:d]thiazolo[3,2-a]pyrimidin-5-ones 5 is described. The key intermediate, 7-(3-amino-2-benzofuran)-5H-thiazolo[3,2-a]pyrimidin-5-one (3), was synthesized from 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one (1) with salicylonitrile (2) by Thorpe-Ziegler isomerization. Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet-Spengler reaction provided benzofuro-fused thiazolo[3,2-a]pyrimidines under sulfamic acid as catalyst in good yields.

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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: 1st February, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13408
Synthesis of A New Chiral C2-Symmetric Nhc-AuCl Complex

Naoya Okitsu, Takuya Yoshida, Kensuke Usui, and Masahisa Nakada*

*Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

A New chiral C2 symmetric NHC ligand with two binaphthyl units has been synthesized. The new NHC ligand features two seven-membered rings that link the imidazolylidene with the binaphthyl units. X-Ray crystallographic analysis of the new NHC-AuCl complex indicates that the Au-Cl bond is located between the phenyl groups of the binaphthyl units and suggests that this arrangement could induce enantioselectivity in reactions. Indeed, catalytic asymmetric ene-yne cyclization of 2b in the presence of a catalytic amount (5 mol%) of cationic complex of 13 quantitatively afforded the cyclized product with 78% ee.

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Published online: 28th January, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-15-830
Total Biosynthesis of Fungal Indole Diterpenes Using Cell Factories

Atsushi Minami, Chengwei Liu, and Hideaki Oikawa*

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

Abstract

Reconstitution of biosynthetic genes in a heterologous host is a newly emerging method for synthesis of fungal secondary metabolites. Application of this method to indole diterpenes is described. We have successfully elucidated all of the individual enzymatic steps and produced four representative indole diterpenes, paspaline, paxilline, aflatrem, and penitrem, at a yield of ~100 mg/L. These results confirmed that the Aspergillus oryzae expression system is highly reliable for elucidation of biosynthetic pathways, even those involving 17 enzymatic reactions.

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Published online: 28th January, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13379
Preparation of (+)-Biotin: Process Development and Scale-Up

Fei Xiong,* Jin Li, Gen Li, Bo Song, Yu-Xiao Zhou, Fen-Er Chen, and Dan Li

*Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China

Abstract

A practical asymmetric total synthesis of (+)-biotin based upon the chiral bifunctional sulfamide 8-promoted enantioselective anhydride desymmetrization has been achieved via the key chiral intermediacy of (3aS,6aR)-1,3-bis(4-methoxybenzyl)tetrahydro-4H-thieno[3,4-d]imidazole-2,4(1H)-dione (4). In addition, the installation of the 4-carboxybutyl side chain at C-4 position of 4 was efficiently introduced by an improved C4+C1 strategy.

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Published online: 20th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13384
Synthesis, Molecular Docking and Antihuman Breast Cancer Activities of Novel Thiazolyl Acetonitriles and Thiazolyl Acrylonitriles and Their Derivatives Containing Benzenesulfonylpyrrolidine Moiety

Mahmoud S. Bashandy* and Shimaa M. Abd El-Gilil

*Department of Chemistry, Al-Azhar University, Nasr City, Cairo 002, Egypt

Abstract

This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 3, 8-10, 13, 19, 20, 24, 30, 31, 35-41, pyrazolo[5,1-c][1,2,4]triazine 5, 1H-1,2,4-triazole 6, thiazolo[3,2-a]pyridine 14, chromen-2-one 16, benzo[f]chromen-3-imine 17, benzo[f]chromen-3-one 18, triazolo[4,3-a]pyrimidine 22, pyrazolo[1,5-a]pyrimidine 23, isoxazole 26, 2,4-diaminopyrimidine 27, benzo[4,5]imidazo[1,2-a]pyridine 28, imidazolidine 32 and 1H-benzo[d]imidazolidene 33 moieties, starting with 2-(4-(4-(pyrrolidin-1-ylsulfonyl)phenyl)thiazol-2-yl)acetonitrile (2), which was prepared from cyclocondensation of phenacyl bromide derivative 1 with 2-cyanoethanethio-amide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR and Ms spectral data. All the compounds were tested in-vitro antihuman breast cancer cell line (MCF7). Compounds 18, 8, 41 and 28 with IC50 values of 48.01, 49.11, 49.27 and 49.78 µM, respectively, exhibited better activity than doxorubicin (DOX) as a reference drug with IC50 value of 68.6 µM. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.

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Published online: 18th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13345
Preparation of Nicotinoyl Amino Acid Derivatives by Fmoc-Solid Phase Synthesis and Preliminary Studies on the DNA-Binding Properties of Nicotinoyl Derivatives

Dongxin Zhao* and Kui Lu*

*School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China

Abstract

Three types of nicotinoyl amino acids, i.e., nicotinoyl leucine (NA-Leu), NA-Leu-His, and NA-Tyr-Tyr, were synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase HPLC, and characterized by 1H, 13C NMR and ESI-MS. The interactions of nicotinic acid and nicotinoyl derivatives with ctDNA were investigated by fluorescence spectroscopy. NA-Leu-His and NA-Tyr-Tyr exhibited higher affinity for ctDNA compared with free NA, indicating that the imidazolyl of histidine and the phenol group of tyrosine can enhance the embedding interaction of nicotinoyl derivatives into ctDNA. In addition, leucine in the derivatives helped form a special surrounding and spatial structure to interact with ctDNA. The stronger interaction of NA-Tyr-Tyr and NA-Leu-His with ctDNA suggested that the modified nicotinic acid probably erhaps had significant practical value and should be further studied.

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Published online: 18th January, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13358
An Efficient Conversion of Lysine to 2-Aminocaprolactam

Hiroshi Matsumoto, Kouji Kaiso, and Akio Kamimura*

*Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, , Japan

Abstract

Treatment of lysine in wet MeOH at high-temperatures provided a smooth and efficient conversion to 2-aminocaprolactam that is recognized as a potential intermediate for the preparation of bioactive compounds. The obtained 2-aminocaprolactam underwent very rapid racemization under these conditions. A kinetic study of the reaction was performed.

PDF (585KB)

Published online: 18th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13389
Design, Synthesis and Anticancer Activity of Novel 2,3- and 2,4-Disubstituted Quinazoline and Quinazolinone Derivatives

Maher El-Hashash, Jehan Morsy, Mohamed Azab,* and Naglaa Mahmoud

*Chemistry of Department, Ain Shams University, Abbassia, Cairo 11566, Egypt

Abstract

An acetylhydrazide derivative containing a quinazoline nucleus has been utilized to design and synthesize a series of 2,4-disubstituted quinazolines via reaction with several carbon electrophiles including 4-methoxybenzaldehyde and carbon disulfide as well as acetyl and benzoyl chloride. Another series of 2,3-disubstituted-4(3H)-quinazolinones has been also obtained from reactions of a 3-aminoquinazolin-4(3H)-one derivative with other carbon electrophiles, such as chloroacetamide, acetic anhydride, phenyl isocyanate, and ethyl chloroacetate. The structures of the new compounds have been assigned from their spectral data (IR, 1H NMR, 13C NMR and MS) and elemental analyses. The newly synthesized compounds were evaluated for their in vitro cytotoxic activity against breast cancer, hepatocellular carcinoma, cervical cancer, and human promyelocytic leukemia cell lines. All the tested compounds showed anticancer activity.

PDF (418KB)

Published online: 15th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13329
Design, Synthesis, Antitumor and Antimicrobial Activity of Some Novel 6,7-Dimethoxyquinazoline Derivatives

Asmaa E. Kassab,* Ehab M. Gedawy, Zienab Mahmoud, and Rania A. Khattab

*Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Cairo University, 33 Kaser El Ainin Street 11562, Egypt

Abstract

Novel 4-substituted-6,7-dimethoxyquinazolines 3, 4a and 4b were synthesized via reacting the corresponding 4-chloro derivative 2 with 2-(4-aminopiperazin-1-yl)ethanol, ethylpiperazine or benzylpiperidine. Quinazolines 6a-c and 8a-d were obtained through reacting 4-hydrazinylquinazoline 5 with different aromatic aldehydes or aromatic isothiocyanates. An attempt to synthesize 6,7-dimethoxyquinazolin-4-yl hydrazinecarboxamides via reacting the hydrazinyl derivative 5 with certain aromatic isocyanates was unsuccessful and the unexpected triazoloquinazoline 7 was obtained regardless to the isocyanate used .The anticancer activity of 4 compounds, namely 3, 4a, 4b and 7 was evaluated by National Cancer Institute (USA) at single dose (10-5 M) utilizing 59 different human tumor cell lines. Moreover, the antimicrobial activity of all the newly synthesized quinazolines was screened against Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram negative bacteria (Escherichia coli and Klebsiella) and a fungal strain (Candida albicans).

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Published online: 15th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13343
Synthesis of Novel Benzimidazoles 2-Functionalized with Pyrrolidinone and γ-Amino Acid with a High Antibacterial Activity

Vestina Strelciunaite,* Kazimieras Anusevicius, Ingrida Tumosiene, Jurate Siugzdaite, Ilona Jonuskiene, Irena Ramanauskaite, and Vytautas Mickevicius

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

Abstract

Series of 2- and 1,2-disubstituted benzimidazoles with carboxyalkyl substituents or their derivatives were synthesized during chemical transformations of 4-(1H-benzimidazol-2-yl)-1-(3-chloro-4-methoxyphenyl)pyrrolidin-2-one. Condensation products of 2-{2-[1-(3-chloro-4-metoxylphenyl)-5-oxo- 3-pyrrolidinyl]-1H-benzimidazol-1-yl}acetohydrazide and 3-(1H-benzimidazol- 2-yl)-4-(3-chloro-4-methoxyphenylamino)butanoic acid hydrazide with mono- and dicarbonylic compounds have been obtained. Some of the synthesized compounds are characterized by a strong bactericidal effect, even at low concentrations.

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Published online: 15th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13373
Synthesis of 6,7-Dihydropyrido[2,3-d]pyrimidin-5(8H)-one Derivatives Based on the Reaction of 1-(4-Chloropyrimidin-5-yl)alk-2-en-1-one Derivatives with Primary Amines

Kazuhiro Kobayashi,* Ryoga Ono, Kouki Ishitobi, Yuuki Chikazawa, Hidetaka Hiyoshi, and Kazuto Umezu

*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 sequence for the synthesis of 6,7-dihydropyrido[2,3-d]pyrimidin-5(8H)-one derivatives has been developed. Thus, treatment of 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine with lithium diisopropylamide (LDA) generates 4-chloro-5-lithio-6-methoxy-2- (methylsulfanyl)pyrimidine, which are allowed to react with α,β-unsaturated aldehydes to give the corresponding 1-(4-chloropyrimidin-5-yl)alk-2-en-1-ol derivatives. Oxidation of these alkenols with activated manganese(IV) oxide provides 1-(4-chloropyrimidin-5-yl)alk-2-en-1-one derivatives, of which reaction with a variety of primary amines constitutes tetrahydropyridinone structure to give the desired products.

PDF (365KB)

Published online: 15th January, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13383
Design, Synthesis and Evaluation of an L-Dopa-Derived Macrocyclic Hexaoxazole (6otd) as a G-Quadruplex-Selective Ligand

Takahiro Nakamura, Yue Ma, Keisuke Iida, Terumi Ohtake, Hiroyuki Seimiya, and Kazuo Nagasawa*

*Biotechnology and Life Science, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Tokyo 184-8588, Japan

Abstract

G-Quadruplex (G4) structures in guanine-rich oligonucleotides are involved in replication, transcription and translation processes in cells, and G4 dysfunction is associated with various diseases. Since G4 stabilization is believed to induce growth inhibition, senescence or apoptosis of cancer cells, various G4-stabilizing agents (G4 ligands) have been synthesized, including our recently developed series of macrocyclic polyoxazoles (OTDs). Among OTD derivatives, those bearing side-chain functional groups that interact with phosphate of the DNA backbone show potent G4-stabilizing ability. Here, we report synthesis of a new macrocyclic hexaoxazole bearing two catechol side chains, i.e., D2H4–6M(4)OTD, based upon our previously reported procedure. D2H4–6M(4)OTD showed moderate and selective stabilizing ability towards G4-forming oligonucleotides without altering their topology. It also showed moderate growth-inhibitory activity towards several cancer cell lines.

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Published online: 14th January, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-15-833
Mesoionic Tetrazoles – Progress Since 1980

Dietrich Moderhack*

*Institute of Medicinal and Pharmaceutical Chemistry, Technical University, Braunschweig, Beethovenstrasse 55, D-38106, Germany

Abstract

This article summarizes the findings made during the past decades with the traditional classes of mesoionic tetrazoles of type (A) and (B); it also deals with the 'abnormal' carbenes derived therefrom. – Emphasis is placed on preparative aspects.

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Published online: 14th January, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13386
Inhibition of NF-κB and Cellular Invasion by Novel Flavonoid Dismal in Ovarian Carcinoma Cells

Liyan Wang, Yinzhi Lin, Kulrawee Sidthipong, Jianqiang Tang, Mengjie Li, Takashi Koyano, Thaworn Kowithayakorn, Kengo Sumiyoshi, Tamami Ukaji, and Kazuo Umezawa*

*Molecular Target Medicine, School of Medicine, Aichi Medical university, 1-1 Yazako-Karimata, Nagakute-shi, Aichi 480-1195, Japan

Abstract

In the course of our screening of NF-κB inhibitors, we isolated known flavonoids that inhibit LPS-induced NO production in mouse monocytic leukemia RAW264.7 cells. Since those flavonoids inhibited the NF-κB activity, we have evaluated the inhibitory activity of plant-derived novel flavonoid, desmal, on NF-κB, and found that it inhibits LPS-induced NO production and NF-κB. It also inhibited cellular invasion possibly by the decrease of NF-κB-dependent urokinase-type plasminogen activator. Thus, desmal was found to be a new NF-κB inhibitor having cellular anti-inflammatory and anti-metastatic activities.

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Published online: 6th January, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)42
Formal Total Synthesis of Artocarpin

Isao Mizota, Kana Taniguchi, and Makoto Shimizu*

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurimamachiya-cho Tsu, Mie 514-8507, Japan

Abstract

A formal total synthesis of artocarpin was achieved via selective demethylation, iodination, followed by Suzuki-Miyaura coupling reaction of the key flavone derivative. It took only 7 steps in the overall yield of 55% starting from commercially available 3,5-dimethoxyphenol.

PDF (392KB)

Published online: 25th December, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13331
Two New Isoindolin-1-ones from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activities

Guang-Hui Kong, Yu-Ping Wu, Wei Li, Zhen-Yuan Xia, Qiang Liu, Kun-Miao Wang, Pei He, Rui-Zhi Zhu, Xiao-Xi Si, 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 isoindolin-1-ones, 2-(2-hydroxyethyl)-5-methyl-6-(3- methylbut-2-enyl)isoindolin-1-one (1) and 2,5-dimethyl-6-(3-methylbut-2-enyl) isoindolin-1-one (2), 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 and 2 were tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results revealed that compounds 1 and 2 showed potential anti-TMV activities with inhibition rates of 48.2 and 45.6%, respectively.

Supporting Info. (658KB)PDF (1MB)

Published online: 24th December, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13362
Cytotoxic Compounds from Scolopendra subspinipes mutilans

Yu-Ming Liu,* Jian-Bing Nie, Lin-Na Sun, and Qing-Hua Liu

*Department of Pharmacy Engineering, Tianjin University of Technology, No.391, Bin Shui Xi Road, Xi Qing District, Tianjin , China

Abstract

A new amino acid, 2S-3-(1-methyl-1H-imidazol-5-yl)-2- (methylamino)propanoic acid (1) and a new natural product, 3, 5-dihydroxyquinoline (2), along with a known compound (3) were isolated from the centipede Scolopendra subspinipes mutilans L. Koch. Their structures were elucidated on the basis of extensive one-dimensional (1D)- and 2D-NMR spectroscopic analyses and mass spectrometry. All isolates were evaluated for their cytotoxic activities against three human cancer cell lines, HepG-2, HT-29, and A549. Compounds 2 and 3 exhibited moderate cytotoxic activities with IC50 values of 1.95–27.20 μM against the three cancer cell lines.

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Published online: 24th December, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13381
Experimental Investigation of Tetracyclic Compounds Containing a Nine-Membered Sultam via Cobalt Alkyne Complexes

Kyosuke Kaneda,* Misuzu Fujita, and Risa Naruse

*Hokkaido Pharmaceutical University, 7-Jo 15-4-1 Maeda,Teine,Sapporo,Hokkaido 006-8590, Japan

Abstract

The synthesis, reactivity, and stereochemistry of nine-membered sultams fused with cobalt alkyne complexes using sequential Nicholas and Pauson–Khand reactions are reported. Novel tetracyclic compounds containing nine-membered sultam moieties were characterized by NMR spectroscopy and X-ray crystallography.

Supporting Info. (4.2MB)PDF (1.1MB)

Published online: 3rd December, 2015

Communication | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)54
Unexpected Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline with Various Nucleophiles

Etsuji Okada,* Mizuki Hatakenaka, Yoshinori Takezawa, and Keisuke Iwakuni

*Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

Aromatic nucleophilic substitution reaction of 4-dimethyl- amino-2-methoxy-3-trifluoroacetylquinoline with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively to give the corresponding Me2N-Nu exchanged products, 2-methoxy-3-trifluoroacetyl- 4-quinolylamines, sulfides, and ethers without any formation of MeO-Nu exchanged products in spite of the common knowledge that alkoxy group is the better leaving group than amino group.

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Published online: 27th November, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13324
P-Stereogenic Diphosphacrowns: Facile Incorporation of Aromatic Rings

Ryosuke Kato, Hiroyuki Watanabe, Yasuhiro Morisaki,* and Yoshiki Chujo*

*Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan

Abstract

P-Stereogenic diphosphacrowns containing naphthalene and pyridine rings were synthesized. Facile incorporation of aromatic rings, and chains of different lengths, into the diphosphacrown skeleton was achieved by altering the electrophile in our previously reported synthetic method. Pyridine-containing diphosphacrown exhibited chiral recognition ability for chiral ammonium salts and carboxylic acids. This is the first example of chiral recognition using P-stereogenic diphosphacrowns. 1H and 31P NMR spectra indicated that the nitrogen, oxygen, and chiral phosphorus atoms contributed to the chiral recognition cooperatively.

FREE:PDF (931KB)

Published online: 30th October, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)53
Practical Synthesis of Tricyclic Lactam Model of Antitumor Renieramycin-Saframycin Natural Products

Masashi Yokoya, Akiya Fujino, Ayako Yaguchi, Miku Yamazaki, and Naoki Saito*

*Department of Medicinal Chemistry, Pharmaceutical Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

A practical synthesis of the tricyclic lactam model compound of antitumor renieramycin-saframycin natural product starting from 2-hydroxy-4,5-dimethoxy-3-methylbenzaldehyde in eleven steps was described. A tosyl group was used for protection of a phenol during this transformation. The overall yield of the target compound was 23%.

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Published online: 29th October, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)13
Chemical Reactivity and Application of 4-Alkylidene-3H-pyrazol-3-ones: Synthesis and Antifungal Activity of Polysubstituted Pyrazoles

Hiroshi Maruoka,* Masataka Hokao, Nobuhiro Kashige, Eiichi Masumoto, Fumi Okabe, Reiko Tanaka, Fumio Miake, Toshihiro Fujioka, and Kenji Yamagata

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

Abstract

Chemical reactivity and application of 4-alkylidene-3H-pyrazol-3-ones are described. Furthermore, twelve of the newly synthesized O-substituted pyrazoles were evaluated for their antifungal activity in vitro against Candida albicans and Saccharomyces cerevisiae.

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