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Published online: 25th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13461
Synthesis, Biological Evaluation of Some New Thiophene Derivatives

Sraa Abu-Melha*

*Department of Chemistry, Faculty of Science of Girls, King Khaled University, Abha 00966, Saudi Arabia

Abstract

The reaction of 2-pyridylacetophenone (2) with phenyl isothiocyanate gave thiocarbamoyl derivative 4, which reacted with α-halocarbonyl compounds in a mixture of ethanol and N,N-dimethylformamide in the presence of triethylamine afforded thiophenes 6, 8, 10, 12 and 14 derivatives. While, when the same reaction was carried out in ethanol without N,N-dimethylformamide, it afforded the corresponding acyclic compounds 5, 7, 9, 11 and 13 which on reflux in N,N-dimethylformamide in the presence of triethylamine gave the corresponding thiophene derivatives. The newly synthesized compounds were characterized by analytical, spectral data and evaluated their antimicrobial activities. Compounds 6, 8, 10, 12, 13 and 14 were found to have high antimicrobial activities.

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Published online: 25th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13468
Stereoselective Synthesis of Chiral α,β-Unsaturated tert-Butyl Sulfoxides Derivatives by the Horner-Wasworth-Emmons Reaction

Bo Liu, Lingyan Chen, and Zhihua Sun*

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Rd., Songjiang, Shanghai, 201620, China

Abstract

A series of chiral α,β-unsaturated tert-butyl sulfoxides derivatives was synthesized by the Horner-Wadsworth-Emmons reaction in good (E)/(Z) ratios. The enantioselectivity up to 89% and the yield up to 90% were achieved. These sulfoxides could be important intermediates in asymmetric synthesis.

Supporting Info. (3.8MB)PDF (510KB)

Published online: 25th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13471
Design and Synthesis of Benzothiazole Schiff Bases of Potential Antitumor Activitiy

Thuraya Al-Harthy, Raid Abdel-Jalil,* Wajdi Zoghaib, Maren Pflüger, Elisabeth Hofmann, and Harald Hundsberger

*Department of Chemistry, Sultan Qaboos University, P.O.Box 36 Al-Khoud 123, Oman

Abstract

In an attempt to develop a new class of selective antitumor agents, a novel series of benzothiazole derivatives was prepared via the condensation of 5-fluoro-6-(4-methylpiperazin-1-yl)benzo[d]thiazol-2-amine with aromatic aldehydes. The preliminary bioassay reveals that (4-fluorobenzylidene)-[5-fluoro-6-(4-methylpiperazin-1-yl)-benzothiazol-2-yl]-amine show specific anticancer cytotoxicity.

PDF (412KB)

Published online: 25th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13489
Approach to Phenanthroindolizidine Alkaloids Using Organic Azides with 1-Aryl Allylic Alcohols: Unexpected Tamdem Reactions to Indenyl Aziridines via Nazarov Cyclization

Taiki Yokoi, Takahiro Sugiura, Hiroki Tanimoto,* Tsumoru Morimoto, Yasuhiro Nishiyama, and Kiyomi Kakiuchi

*Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan

Abstract

Organic azide cyclization reactions with 1-aryl allylic alcohols were investigated in a synthetic study of phenanthroindolizidine alkaloids. Unsaturated imines (enimines) were effectively obtained from the allylic alcohol adjacent to electron-rich aromatic rings under thermal reaction conditions. The tandem aziridination-Nazarov reactions to indenyl aziridines were preferred to the acid-mediated enimine formation via Schmidt reaction in the case of 3-aryl diallylic alcohols.

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Published online: 24th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13455
Synthesis of Quercetin Glycosides and Their α-Glucosidase Inhibitory Activities

Bixue Xu,* Guangyi Liang,* Zhonghang Wen, Zhanxin Hu, Jie Yuan, Hongju Chen, and Limei Zhang

*The Key Laboratory of Chemistry for Natural Products of Guizhou province and Chinese Academy of Sciences, Guiyang 550002, Guizhou, China

Abstract

A series of quercetin glycosides as the analogues of 3,5,5'-trimethyl-7-O-β-D-glucopyranosylquercetin (8) were synthesized, their structures were confirmed by 1H NMR, 13C NMR and MS. The inhibitory activities of those compounds against α-glucosidase were evaluated in vitro, in particular, the compounds V-c and V-d-2 showed promising bioactivities with IC50 of 19.4 μmol·L–1 and 19.7 μmol·L–1, are much higher than 8 (IC50 > 100 μmol·L–1). This research will provide a reference in the study of the synthetic methods and hypoglycemic activity for the quercetin glycosides.

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Published online: 20th May, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13475
A Colorimetric Chemosensor Based on Fluorescein for the Detection of Zn2+ in Aqueous Solution

Wei Wang, Ya-Nan Lei, Qing-Lei Liu, and Yan Gao*

*Department of Chemical Engineering, University of Science and Technology Liaoning, High-tech Zone of Anshan, Liaoning Province 114051, China

Abstract

A novel quinoline-functionalized fluorescein derivative HL was designed and used as a colorimetric chemosensor for the detection of Zn2+ over other commonly coexistent metal ions in aqueous solution at pH 7.2. Studies on its binding with different metal ions revealed a noticeable naked eye color change in the presence of Zn2+. The mechanism has been supported by Job’s plot evaluation, MS and 1H NMR spectroscopic studies. The association constant and the detection limits of sensor HL to Zn2+ were determined as 1.17×105 M-1 and 5.7 nM. This excellent selectivity and sensitive of HL to Zn2+ exhibited its potential application value in the biological monitoring and tracking of Zn2+.

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Published online: 19th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13476
Synthesis and DNA Cleavage Activity of Functionalized Pyrazol-3-ones Containing Oxime Ester

Eiichi Masumoto, Nobuhiro Kashige, Fumi Okabe, Fumio Miake, Kenji Yamagata, and Hiroshi Maruoka*

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

Abstract

A facile access to the synthesis of functionalized pyrazol-3-ones containing oxime ester from 4-hydroxypyrazol-3-ones, which were prepared starting from 4-alkylidenepyrazol-3-one, in moderate to good yields is reported. The structures of all products were identified by spectral data and some synthesized compounds were tested for their DNA cleavage activity.

PDF (305KB)

Published online: 16th May, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13480
Synthesis of the New Heterocyclic System 5,6,10b-Triazaacephenanthrylene, a Nitrogen Analogue of Aristolactams

Katarzyna Ostrowska,* Karol Dudek, and Bogdan Musielak

*Department of Organic Chemistry, Jagiellonian University, R.Ingardena 3, PL-30-060 Kraków, Poland

Abstract

We describe the two-step sequence for transforming enaminothioenone 1 to the planar semicyclic amidine 2 via an ylidenemalononitrile enamine intermediate, leading to the formation of the new π-conjugated heterocyclic system 5,6,10b-triazaacephenanthrylene, structurally related to the naturally occurring alkaloid aristolactams.

Supporting Info. (1.7MB)PDF (474KB)

Published online: 16th May, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13479
Prospective Study Directed to the Synthesis of Symmetrical Linked Bis-Rhodanine Derivatives with Their Antimicrobial Activity

Wael A. A. Arafa,* Raafat M. Shaker, and Saleh A. Rabeh

*Department Of Chemistry, Fayoum University, Fayoum 12975, Egypt

Abstract

One-pot three-component reactions of diamines, carbon disulfide and dialkyl acetylenedicarboxylates under conventional or ultrasound methods furnishing bis-rhodanines in good yields are described. Knoevenagel condensation reaction between 5,5’-methylene-bis-salicyaldehyde, pyrazole-3,5-dicarbaldehyde or terephthalaldehyde and N-alkylrhodanines afforded bis-arylidenerhodanines. While, the condensation between 2,6-diformylphenols and N-alkylrhodanines furnished only the mono-arylidenerhodanines. The newly synthesized compounds were characterized by HRMS and NMR spectral data. The compounds were screened for their in vitro antimicrobial activities. All the tested compounds showed pronounced activities, suggesting that the rhodanine moiety plays an important role in enhancing the antimicrobial properties of this class of compounds.

PDF (482KB)

Published online: 10th May, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13459
Highly C3-Selective Direct Alkylation and Arylation of 2-Pyridones under Visible-light-promoted Photoredox Catalysis

Atifah Najib, Sho Tabuchi, Koji Hirano,* and Masahiro Miura*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 560-0871, Japan

Abstract

An Ir photoredox catalyst-mediated highly site-selective direct alkylation and arylation of 2-pyridones has been developed. Under visible-light-promoted conditions, ethyl 2-bromo-2,2-difluoroacetate couples with various 2-pyridones exclusively at the C3 position. A similar photoredox catalysis is also effective for the direct C3-arylation with diaryliodonium triflates. Thus, these reactions occurs under very mild conditions (blue LEDs irradiation and ambient temperature) to form the corresponding C3-alkylated and arylated 2-pyridones of potential interest in medicinal and pharmaceutical chemistry.

Supporting Info. (9.8MB)PDF (670KB)

Published online: 28th April, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13464
Synthesis and Antileukemic Activity of New Fluorinated 5-Aza-9-deazapurines

Felicia Phei Lin Lim, Koon Kee Kow, Eng Hwa Yeo, Sek Chuen Chow, and Anton V. Dolzhenko*

*School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Subang Jaya, Selangor 47500, Malaysia

Abstract

Novel fluorinated 4-benzylamino-7-phenylpyrazolo[1,5-a]- [1,3,5]triazin-2-amines were prepared using an efficient and practical approach. The chemoselectivity of condensation of pyrazolylguanidine and trichloroacetonitrile was found to be solvent-dependent and, when conducted in toluene, this reaction afforded 7-phenyl-4-trichloromethylpyrazolo[1,5-a]- [1,3,5]triazin-2-amine as the main product. This key intermediate underwent nucleophilic replacement of the trichloromethyl group with fluorinated benzylamines providing a series of the target compounds. Antiproliferative activity of the prepared compounds against Jurkat T cells was explored using MTS assay. Morphological changes observed in cells treated by the most potent compounds of this series, suggested that these compounds induced apoptosis in cells.

PDF (772KB)

Published online: 28th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13477
Efficient One-Pot Synthesis of Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives under Copper-Catalyzed Conditions

Jiyang Jie, Haoyi Li, Meihui Piao, and Xiaobo Yang*

*College of Chemistry & Chemical Engineering, Shenyang Normal University, 253 Huanghe North Street Shenyang, China

Abstract

An efficient method has been developed for the synthesis of benzo[e]pyrazolo[1,5-c][1,3]thiazines via one-pot two-step reactions of readily available substituted 1-(2-halophenyl)-3-akylprop-2-yn-1-ones, hydrazine hydrochloride and β-oxodithioesters under mild conditions, and the corresponding benzo[e]pyrazolo[1,5-c][1,3]thiazines were obtained in good to excellent yields. The novel method affords a new strategy for the construction of diverse and useful poly N,S-heterocyclic compounds.

PDF (295KB)

Published online: 27th April, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13465
A One-Pot Synthesis of Phaitanthrin E Through Intermolecular Condensation/Intramolecular Aryl C-H Amination Cascade

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

A one-pot synthesis of phaitanthrin E starting from methyl indole-3-carboxylate and isatoic anhydride through intermolecular condensation/intramolecular aryl C-H amination cascade was developed.

PDF (1.1MB)

Published online: 26th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13458
Selective Synthesis of Monosubstituted p-tert-Butylthiacalix[4]arene under Phase Transfer Catalysis

Omran A. Omran*

*Medical laboratory department, College of Science, Majmaah University, Zulfi, 1712, 11932, Saudi Arabia
Chemistry Department, Faculty of Science, Sohag University, Sohag, 82524, Egypt

Abstract

Phase transfer catalysis (PTC) technique for lower rim alkylation of p-tert-butylthiacalix[4]arene (TCA) with diethyl bromomalonate, phenacyl bromide, N,N-diethylchloroacetamide, ethyl bromoacetate and chloroacetonitrile using K2CO3, CsOH or Na2CO3 as a base and tetraethylammonium bromide (TEAB) as catalyst in benzene has been employed. Selective synthesis of monosubstituted p-tert-butylthiacalixarene using K2CO3 or CsOH as base has been elaborated. Unprecedented alkylation cyclization as well as arene oxidation by using of Na2CO3 as a base for alkylation of p-tert-butylthiacalix[4]arene under PTC conditions led to the synthesis of two new p-tert-butylthiacalix[4]arene derivatives with heterocyclic bridging rings. The structures of the newly synthesized compounds were characterized by different spectroscopy methods IR, 1H NMR, 13C NMR, and single crystal X-ray diffraction.

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Published online: 18th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13442
A Biomimetic Approach to the Synthesis of Terpene-Amino Acid Conjugates. The Ugi Reaction in the Hypothetical Biosynthesis of Marine Natural Products

Yoshiyasu Ichikawa,* Kenta Saito, Rika Mimura, Ayumi Kitamori, Akihito Matsukawa, Akifumi Ikeda, Toshiya Masuda, Hiyoshizo Kotsuki, and Keiji Nakano

*Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan

Abstract

A unique pathway for the biosynthesis of the marine sponge terpenes, exigurin and boneratamides A–C, is proposed. Based on this proposal, a biomimetic strategy on key Ugi coupling reactions between terpene isocyanides and amino acids was developed for construction of the core structures of exigurin and boneratamides A–C.

PDF (1.5MB)

Published online: 14th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13445
An Efficient Route for Synthesis and Reactions of Seleno-[2, 3-c]coumarin

Shams H. Abdel-Hafez,* Ahmed Elkhateeb, Adel A. Gobouri, Islam H. El Azab, and Gilbert Kirsch

*Department of Chemistry, Faculty of Science, Taif University, Taif-Al-Haweiah 888/21974, Saudi Arabia

Abstract

Synthesis of new selenium-containing coumarin moiety via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium borohydride gave 3-Cyano-4-coumarinselenol which reacted with different halo-acids, such as chloroacetonitrile, ethyl chloroacetate and chloroacetamide to give the corresponding 3-amino-4-oxo-4H-seleno[3,2-c]chromene-2- derivatives. Hydrazonolysis of the obtained new ethyl 3-amino-4-oxo-4H-seleno[3,2-c] chromene-2-carboxylate afforded the corresponding hydrazino compound. The hydrazino compound was used as a versatile precursor for synthesis of new other heterocyclic compounds containing selenocoumarin moiety. The newly synthesized compounds were characterized using the spectroscopic tools (IR, 1H NMR, 13C NMR and mass spectroscopy) as well as microanalysis.

PDF (971KB)

Published online: 8th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13430
1-Methylimidazolium Trifluoroacetate Efficiently Catalyzed Three Component Synthesis of Diazaspiro[5.5]undecane-1,5,9-trione Derivatives under Solvent-Free Conditions

Zhaohui Xu,* Houfu Zhang, Chunhua Lin, and Deyong Liu

*College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330027, China

Abstract

A simple, green and efficient method for the synthesis of 2,4-dioxa- 8,10-diazaspiro[5.5]undecane-1,5,9-trione derivatives has been developed by the reaction of aromatic aldehydes with urea and 1,3-dioxane-4,6-dione catalyzed by 1-methylimidazolium trifluoroacetate under solvent-free conditions.

PDF (1.2MB)

Published online: 8th April, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-16-841
Latest Development on the Methods of Synthesizing Ionic Liquids

Xiaoxia Xie, Lihua Li, Xian Wu, Cheng Ma, and Jinsheng Zhang*

*Department of Chemical Engineering and Environment Engineering, College of Chemistry, Liaoning Shihua University, Fu Shun, Liaoning Province, 113000, China

Abstract

Nowadays, in spite that the application of ionic liquids in some domains is still at infancy stage, the related synthetic technologies have got tremendous development over one century. In this paper, we made an overview on characteristics of five approaches to synthesize ionic liquids and compared the advantages and disadvantages of different methods, and gave recommendations for the best means of synthesizing to the objectives of related studies. Finally, the present work provides a full-scale literature review of the implementation of synthesizing ionic liquids, which could assist the corporations or individuals to search for the most suitable methods and lay the foundation for exploiting more ideal methods to obtain high purity and better yields of ionic liquids in the future.

PDF (447KB)

Published online: 8th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13450
Synthesis of 1-Aroyl-1,2-dihydro-3H-indol-3-ones via Cyclization of N-[2-(2-Chloroacetyl)phenyl]benzamides with Triethylamine in the Presence of Di-tert-butyl Dicarbonate

Kazuhiro Kobayashi,* Daiki Kado, and Kohei Nishikawa

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

Abstract

1-Aroyl-1,2-dihydro-3H-indol-3-ones can now be conveniently obtained from 2-aryl-4-(Z)-(chloromethylidene)-4H-3,1-benzoxazines using an easy operated three-step sequence under mild conditions. Thus, the starting materials are hydrolyzed with dilute hydrochloric acid at 0 ˚C to N-[2-(2-chloroacetyl)phenyl]benzamides, of which treatment with triethylamine in the presence of di-tert-butyl dicarbonate at room temperature, followed by deprotection with trifluoroacetic acid at room temperature, provides the desired products.

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Published online: 8th April, 2016

Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13451
Synthesis and Antimicrobial Evaluations of Novel Spiro Cyclic 2-Oxindole Derivatives of N-(1H-Pyrazol-5-Yl)-Hexahydroquinoline Derivatives

Said Ahmed Soliman Ghozlan, Muhammed Ali Ramadan, Amr Mohamed Abdelmoniem,* and Ismail Abdelshafy Abdelhamid*

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

A novel series of interesting spiro cyclic 2-oxindole derivatives of N-(1H-pyrazol-5-yl)hexahydroquinoline derivatives were prepared via the versatile readily accessible cyclic β-enaminones incorporating pyrazole. Antimicrobial evaluations were performed on the prepared compounds. Most of these compounds exhibited high to moderate antimicrobial activity.

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Published online: 5th April, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13452
Concise Synthesis and Biological Evaluation of Chalcone Derivatives Bearing N-Heterocyclic Moieties

Zewei Mao, Xi Zheng, Yuping Lin, Yan Qi, Chunyan Hu, Chunping Wan,* and Gaoxiong Rao*

*Central laboratory, The NO.1 Affiliated Hospital of Yunnan University of Traditional Chinese Medicine, Kunming, 650021, China

Abstract

In this study, we designed and synthesized a series of chalcone derivatives bearing N- heterocyclic moieties, and screened in vitro anti- inflammatory in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and anticancer activity against a panel of human tumor cell lines. The results indicated that compound 9 not only had inhibitory effect on the generation of NO (IC50=8.11μM) and significantly inhibited the production of TNF-α, but also showed better anticancer activity against Hela and SGC7901 (IC50=1.05μM and 6.47μM, respectively), which was identified as the most potent anti-inflammatory and anticancer agent.

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Published online: 5th April, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13453
Synthesis and Antibacterial Evaluation of Some New 5-Substituted Hydantoins and Novel Twin-Drug Type Derivatives

Makoto Furutachi, Fumiko Fujisaki, Reika Tsuru, Ayumi Ejima, Toshiaki Gondo, Saho Goto, Miki Ito, Maki Nakamura, Hatsumi Aki, 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 report the preparation of new oxygen analogues 2 of twin-drug type bivalent mid-size lead molecule 1 and related single-drug type hydantoin derivatives 3. The new twin-drug type oxygen analogues (2a and 2b) also showed significant antibacterial activity against a Gram-positive strain (S. aureus). A comparison of the two types of twin-drug type mid-size compounds 1 and 2 showed that the original lead 1 had a higher level of antibacterial activity against a Gram-positive strain (S. aureus) than those of the compounds (2a and 2b). We also report the results of antibacterial evaluation of prepared compounds and the investigated structure-activity relationships of these molecules.

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Published online: 1st April, 2016

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-16-13439
Furan-2-carboxylic Acids from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activities

Chun-Bo Liu, Xin-Meng Xu, Qin-Peng Shen, Wei Zhang, Xiao-Feng Shen, Ye-Kun Yang, Feng-Mei Zhang, Pei He, Xiao-Xi Si, Ya-Dong Guo, Jian-Jun Xia,* and Guang-Yu Yang*

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

Abstract

Three new furan-2-carboxylic acids, 5-(4-hydroxy-2-methoxy-6-methyl- phenyl)-3-methylfuran-2-carboxylic acid (1), methyl 5-(4-hydroxy-2-methoxy-6- methylphenyl)-3-methylfuran-2-carboxylate (2), and 5-(3-hydroxy-4-methoxy-5- methylphenyl)-3-methylfuran-2-carboxylic acid (3), together with two known furan-2-carboxylic acids (4 and 5) 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-TMV activities. The results showed that compounds 3 and 4 exhibited high anti-TMV activities with inhibition rates of 29.8 and 30.3%. These rates are close to that of positive control. The other compounds also showed potential activities with inhibition rates in the range of 22.8%~25.4%, respectively.

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Published online: 22nd March, 2016

Review | Regular issue | Prepress
DOI: 10.3987/REV-16-840
Diverse and Important Contributions by Medicinal Chemists to the Development of Pharmaceuticals: An Example of Active Vitamin D3 Analog, Eldecalcitol

Noboru Kubodera*

*International Institute of Active Vitamin D Analogs, 35-6, Sankeidai, Mishima, Shizuoka 411-0017, Japan

Abstract

Presented herein are diverse and important contributions by medicinal chemists to different stages of pharmaceutical development. The conceptual elements reviewed, which are intended for young chemists who engage in drug discovery research, draw upon the author’s experience in developing eldecalcitol, an active vitamin D3 analog used to treat osteoporosis. The review covers exploratory research for a lead candidate compound; process development for practical manufacturing; and synthesis of other compounds relevant to the program, such as tritiated compounds, postulated metabolites, and miscellaneous analogs for mode of action studies.

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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.

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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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Published online: 7th January, 2016

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)46
Chemistry of Polyhalogenated Nitrobutadienes, 15: Synthesis of Novel 4-Nitro-3-amino-1H-pyrazole-5-carbaldehydes and Pyrazolo[3,4-f]indazole-4,8-diones

Viktor A. Zapol'skii, Jan C. Namyslo, Mimoza Gjikaj, and Dieter E. Kaufmann*

*Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

Condensation of 1-amino-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3,4,4-trichloro-2-nitrobuta-1,3-dienes 3a-e with methylhydrazine leads to a series of uniquely persubstituted 4nitropyrazoles 4a-e bearing a dichloromethyl substituent in 5-position. Subsequent hydrolysis of this group applying aqueous sulfuric acid then gives interesting push-pull – substituted pyrazole-5-carbaldehydes 5a-e. Upon hydrolysis of 4a-e at harsher reaction conditions different pyrazolo[3,4-f]indazole-4,8-diones were also formed. A mechanism of the homo-condensation of carbaldehydes 5a,d to the indazole derivatives 8-13 is proposed, and as an example the structure of 3,7-bis(dimethylamino)-1,6-dimethylpyrazolo[3,4-f]indazole-4,8(1H,6H)-dione (9) has been confirmed by X-ray analysis.

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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.

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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: 1st December, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)55
Synthesis of 7,7′-Linked-bis-indoles via 7-Tryptamines

Hakan Kandemir, Ibrahim F. Sengul, Christopher R. Gardner, Eryn L. Werry, Melissa L. Barron, Michael Kassiou, Naresh Kumar, and David StClair Black*

*School of Chemistry, The University of New South Wales, Sydney 2052, Australia

Abstract

The synthesis of 7-tryptamines was accomplished via the reduction of 7-nitrovinylindoles which were developed by the condensation of indole-7-carbaldehydes with nitromethane and ammonium acetate. 7-Tryptamines were subsequently used for the construction of 2,3-disubstituted and 3-substituted 7,7-linked-bis-indoles.

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