Open Access Published by De Gruyter

Volume 19 Issue 4

Issue of Heterocyclic Communications

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Contents
Journal Overview

Masthead

Publicly Available August 2, 2013

Masthead

Page range: i-iii

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Review

Open Access July 5, 2013

Synthesis and photochromism of aryl(heteroaryl)- and diheteroarylethenes – coumarin derivatives

Valerii F. Traven, Andrei Y. Bochkov

Page range: 219-238

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Abstract

In this review, we discuss the synthesis and photochromism of aryl(heteroaryl)- and diheteroarylethenes, containing pyrane ring of coumarin as part of the photosensitive hexatriene system or bearing a coumarin unit as a substituent outside of hexatriene. Coumarinylethenes with noncyclic double bond as well as coumarinyl(thienyl)thiazoles, coumarinyl(thienyl)maleic anhydride (or maleimide) derivatives, and 3,4-bis(thiazolyl)coumarins possess both photochromism and fluorescence switching properties upon UV/vis irradiation.

Preliminary Communications

Open Access July 5, 2013

Fluorescent labeling of oleanolic acid using ‘click’ chemistry

Miaofu Mao, Shuzhang Xiao, Haibo He, Qiong Cao, Kun Zou

Page range: 239-243

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Abstract

The natural product oleanolic acid (OA) was functionalized and labeled with the non-aggregated fluorescent dye BOPIM (boron 2-(2′-pyridyl)imidazole complex) using ‘click’ chemistry, yielding a highly fluorescent probe. The pharmacological activity of the probe is comparable to that of unmodified OA, making it suitable for studying the therapeutic mechanisms of OA derivatives in vitro .

Open Access July 24, 2013

Facile synthetic entry into rotationally restricted 9-arylacridines

Jianguo Zhang, Jarosław Sączewski, Ewa Wolińska, Lucjan Strekowski

Page range: 245-247

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Abstract

The treatment of 2-(trifluoromethyl)aniline with 2,6-dimethylphenylmagnesium bromide yields 1-methyl-9-(2,6-dimethylphenyl)acridine by the formal reaction of one equivalent of the aniline and two equivalents of the Grignard reagent. Interestingly, one of the methyl groups is eliminated during the reaction, and the product contains three methyl groups only. In a similar way, the reaction of 2-(trifluoromethyl)aniline with 2-ethylphenylmagnesium bromide furnishes 9-(2-ethylphenyl)acridine devoid of one ethyl group. The mechanism is discussed.

Research Articles

Open Access August 2, 2013

Selective fluorescence sensing of ferric ion with novel triazolethione Schiff bases probes

Wei Wang, Junwu Wang, Xiaoyu Jiang, Kui Yang, Qiang Zhang, Yan Gao

Page range: 249-252

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Abstract

New triazolethione Schiff base derivatives 3a–f were synthesized. The structures of the products were characterized by elemental analysis, 1 H NMR, 13 C NMR, IR and MS. Their complexation properties to different heavy and transition metal ions were studied by UV-Vis and fluorescence spectroscopy. Compound 3a shows selective recognition of Fe 3+ with a 1:1 stoichiometric complex formation.

Open Access July 12, 2013

Synthesis and antimicrobial activities of some novel thiophene containing azo compounds

Emmanuel Sopbué Fondjo, Joseph Tsemeugne, Jean De Dieu Tamokou, Arnaud Ngongang Djintchui, Jules Roger Kuiate, Beibam Luc Sondengam

Page range: 253-259

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Abstract

A series of new thienylazothiophenes were prepared by coupling reactions of diazotized thienocoumarins with their corresponding free amines. The structures of the products 3–7 were assigned on the basis of their elemental and spectroscopic data. The HMBC and HSQC techniques were used in some cases to ascertain the structural assignments. The antimicrobial screenings of compounds 3–7 along with substituted 2-aminothiophenes 1a,b were performed against three bacteria and three fungal species and their activities compared to those of nystatin, gentamycin and ciprofloxacin used as reference drugs. It was found that the antimicrobial activities of the tested new hybrid compounds were in some cases equal or better than those of the reference drugs.

Open Access July 17, 2013

Effect of intramolecular hydrogen bonding on biomimetic reactions by flavins

Geetanjali, Ram Singh

Page range: 261-263

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Abstract

Selected 6- and 7-carboxyflavins activate H 2 O 2 , oxidizing thioanisole to its sulfoxide. The greater reactivity of the 6-carboxyflavin derivatives are ascribed to the intramolecular hydrogen bonding between N(5) and the carboxyl group of the flavin system.

Open Access July 5, 2013

Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides

Akbar Mobinikhaledi, Naser Foroughifar, Abdolhossein Rafiee

Page range: 265-269

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Abstract

An efficient synthesis of novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives starting from terephthaloyl and isophthaloyl chlorides is described. Terephthaloyl or isophthaloyl chloride was allowed to react with hydrazine hydrate in refluxing ethanol to give a corresponding bis-hydrazide derivative. Further reaction of these compounds with isothiocyanates gave bis-thiosemicarbazide derivatives, which then underwent cyclization to bis-1,3,4-thiadiazoles in the presence of sulfuric acid. The cyclization of these compounds in the presence of sodium hydroxide resulted in the formation of bis-1,2,4-triazole-3-thioles. The structure of these compounds was characterized by IR, NMR, and elemental analysis.

Open Access July 6, 2013

Synthesis of heterocyclic compounds by reaction of dialkyl acetylenedicarboxylates with thiourea derivatives

Hossein Eshghi, Mehdi Bakavoli, Javad Abedini-Torghabeh, Mohammad Rahimizadeh, Amir Keykha

Page range: 271-274

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Abstract

Phosphorus ylides have been prepared in excellent yields by the three-component reaction of activated electron-deficient acetylenic esters (dimethyl and diethyl acetylenedicarboxylate) and thiourea derivatives in the presence of triphenylphosphine. In some cases, these ylides were cyclized to dihydropyrimidothiazine, thioxoimidazolidine, and thioxotetrahydropyrimidine derivatives.

Open Access July 10, 2013

Synthesis of novel 2-arylsulfonylimino-3,4- dimethyl-5-(5-S-substituted [1,3,4]oxadiazol- 2-yl)-2,3-dihydrothiazole derivatives and their plant growth stimulant activity

Karine A. Eliazyan, Ruzanna S. Hakobyan, Vergush A. Pivazyan, Emma A. Ghazaryan, Siranush V. Harutyunyan, Aleksandr P. Yengoyan

Page range: 275-280

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Abstract

2-Arylsulfonylimino-3,4-dimethyl-2,3-dihydrothiazole-5-carboxylic acid hydrazides 2 were obtained from corresponding 2-arylsulfonylimino-4-methyl-2,3-dihydrothiazole-5-carboxylic acid ethyl esters 1 in a two-step synthesis. Heterocyclization of the hydrazide moiety yielded 2-arylsulfonylimino-3,4-dimethyl-5-(5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-2,3-dihydro-thiazoles 3 . Treatment of compounds 3 with various alkyl halides gave corresponding S -substituted derivatives 4–6 . The plant growth stimulant activities of synthesized compounds were compared with those of similar [1,2,4]triazol- and [1,3,4,]thiadiazol-2-yl-thiazoles.

Open Access August 2, 2013

Synthesis and biological activity of 6-substituted 5-acetyl-4,7-dimethoxybenzofuran derivatives

Mariola Krawiecka, Bożena Kuran, Jerzy Kossakowski, Marta Kierzkowska, Grażyna Młynarczyk, Julia Kazmierczak-Barańska, Karolina Królewska, Marcin Cieślak

Page range: 281-286

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Abstract

In the search for new antimicrobial and anticancer agents, a series of (aryl/heteroaryl-piperazino-alkyl)-substituted derivatives of benzo[ b ]furans were prepared. All compounds were characterized by 1 H NMR, 13 C NMR, ESI-MS spectra and elemental analyses. Most of the investigated compounds had no antimicrobial activity (MIC > 512 mg/L) except for 2l , 2m and 2o , which showed activity against Candida albicans . None of the tested compounds showed significant anticancer activity in K562 and HeLa cells.

Open Access July 13, 2013

Synthesis and biological activity of novel series of heterocyclic compounds containing succinimide moiety

Bożena Kuran, Jerzy Kossakowski, Marcin Cieślak, Julia Kazmierczak-Barańska, Karolina Królewska, Michał K. Cyrański, Dorota K. Stępień, Mariola Krawiecka

Page range: 287-296

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Abstract

In the search for biological agents, a series of new N -substituted ethyl 11-ethyl-7-methyl-3,5,10-trioxo-4-azatricyclo[5.2.2.0 2,6 ]undecane-8-carboxylates 3 , 9-methyl-3,5,8-trioxo-4-azatricyclo[5.2.1.0 2,6 ]dec-1-yl acetates 6 and 1,3-dioxo-4,5,6,7-tetraphenyl-2,3,3a,4,5,7a-hexahydro-1 H -isoindole-4-carboxylic acids 9 were prepared. All compounds were characterized by 1 H NMR, ESI-MS, and elemental analyses. Moreover, for intermediate products 2 , 5 , and 8 , X-ray structural analyses were conducted. Compounds 3a–e , 6a, 6b , 9a–e were tested for their cytotoxic properties in K562 and HeLa cells.

About this journal

Topical/Special Issues:

Objective
Heterocyclic Communications (HC) is an open-access, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.

Topics

Development of novel synthetic methods
Significant improvement of known synthetic methods
Chemistry of natural products
Superior biological activity of novel heterocyclic compounds, rational design and synthesis of new drug candidates targeting specific biological receptors
Application of heterocyclic compounds as probes for biomolecules in biophysical and bioanalytical chemistry
Development of new substrates and catalysts in materials chemistry

Article formats
Preliminary Communications, Original Research Articles, Review Articles