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Special Issue "Sulfur-Nitrogen Heteroaromatics"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: closed (10 April 2016)

Special Issue Editors

Guest Editor
Dr. Panayiotis A. Koutentis

Department of Chemistry, University of Cyprus, P. O. Box 20537, 1678 Nicosia, Cyprus
Website | E-Mail
Phone: 0035722892783
Interests: heterocyclic chemistry; sulfur-nitrogen heterocycles; synthetic methods; azaacenes; zwitterionic acenes; stable organic radicals; biologically active heterocycles; isothiazoles; 1,2,3-dithiazoles; 1,2,6-thiadiazines;1,2,4-benzotriazines.
Assistant Guest Editor
Dr. Andreas S. Kalogirou

Department of Pharmacy, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus
E-Mail

Special Issue Information

Dear Colleagues,

Sulfur-nitrogen heteroarenes or hetarenes are cyclic compounds that obey Hückel’s 4n+2 π electron rule for aromaticity and contain, as ring members, at least one sulfur and one nitrogen atom. Hetarenes containing two or more heteroatoms are, in general, less well studied than the monoheteroatom systems (e.g., pyrrole, furan, thiophene, and pyridine). Nevertheless, they are steadily attracting more interest in biological and material sectors. Sulfur-nitrogen hetarenes are a particularly interesting category of mixed heteroatom hetarenes owing to the distinctly different physical properties of sulfur and nitrogen. Not surprisingly, many sulfur-nitrogen hetarene derivates are considered privileged structures by medicinal chemists. Thiazoles or isothiazoles now appear in top selling pharmaceuticals such as Dasatinib (anticancer), Ritonavir (HIV), Ziprasidone (antipsychotic), while 1,2,5-thiadiazole appears in Timolol (non-selective beta-adrenergic receptor antagonist) and its benzo- and pyrido-fused analogues are useful in various organic electronic applications. This Special Issue encourages authors to report new developments in all aspects of sulfur-nitrogen heteroaromatic chemistry.

Dr. Panayiotis A. Koutentis
Guest Editor

Manuscript Submission Information

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Keywords

• heterocycle
• heteroaromatic
• hetarene
• Sulfur-Nitrogen
• thiazole
• isothiazole
• thiadiazole
• thiatriazole
• thiazine
• thiadiazine
• thiatriazine
• ring synthesis
• ring transformations
• aromaticity
• spectroscopy
• medicinal chemistry
• polymer chemistry
• materials chemistry

Published Papers (9 papers)

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Research

Open AccessArticle Synthesis, Characterization and Antibacterial Studies of N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide and Its Neodymium(III) and Thallium(III) Complexes
Molecules 2017, 22(2), 153; doi:10.3390/molecules22020153
Received: 9 November 2016 / Revised: 4 January 2017 / Accepted: 4 January 2017 / Published: 22 February 2017
PDF Full-text (3711 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide (NBTCS) was synthesized by condensation reaction of 4-chlorobenzenesulphonyl chloride and 2-aminobenzothiazole in acetone under reflux. Neodymium(III) and thallium(III) complexes of the ligand were also synthesized. Both ligand and metal complexes were characterized using UV-Vis, IR, 1H- and 13C-NMR spectroscopies,
[...] Read more.
N-(Benzothiazol-2-yl)-4-chlorobenzenesulphonamide (NBTCS) was synthesized by condensation reaction of 4-chlorobenzenesulphonyl chloride and 2-aminobenzothiazole in acetone under reflux. Neodymium(III) and thallium(III) complexes of the ligand were also synthesized. Both ligand and metal complexes were characterized using UV-Vis, IR, 1H- and 13C-NMR spectroscopies, elemental analysis and molar conductance measurement. IR studies revealed that the ligand is tridentate and coordinates to the metal ions through nitrogen and oxygen atoms of the sulphonamide group and nitrogen atom attached to benzothiazole ring. The neodymium(III) complex displays a coordination number of eight while thallium(III) complex displays a coordination number of six. The ligand and its complexes were screened in vitro for their antibacterial activities against Escherichia coli strains (E. coli 6 and E. coli 13), Proteus species, Staphylococcus aureus and Pseudomonas aeruginosa using the agar well diffusion technique. The synthesized compounds were found to be more active against the microorganisms screened relative to ciprofloxacin, gentamicin and co-trimoxazole. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle New Route Synthesis of Thiadiazoles, Bisthiadiazoles, Thiadiazolotriazines, and Pyrazolothiadiazoles Based on Hydrazonoyl Halides and Dihydrazinylthiadiazole
Molecules 2017, 22(2), 336; doi:10.3390/molecules22020336
Received: 1 January 2017 / Accepted: 15 February 2017 / Published: 21 February 2017
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Abstract
Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds
[...] Read more.
Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds to afford new pyrazoles containing thiadiazole compounds. The new synthesized compounds were identified by elemental analysis and various spectral data (Fourier transform infrared spectroscopy, mass spectrometry, 1H and 13C nuclear magnetic resonance). Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle An Efficient Synthesis of Novel Bioactive Thiazolyl-Phthalazinediones under Ultrasound Irradiation
Molecules 2017, 22(2), 319; doi:10.3390/molecules22020319
Received: 15 November 2016 / Revised: 16 January 2017 / Accepted: 14 February 2017 / Published: 18 February 2017
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Abstract
Novel 2-thiazolylphthalazine derivatives were efficiently synthesized under ultrasound irradiation, resulting in high yields and short reaction times after optimization of the reaction conditions. All prepared compounds were fully characterized using spectroscopic methods. They were screened for their antimicrobial activity against Gram-positive and Gram-negative
[...] Read more.
Novel 2-thiazolylphthalazine derivatives were efficiently synthesized under ultrasound irradiation, resulting in high yields and short reaction times after optimization of the reaction conditions. All prepared compounds were fully characterized using spectroscopic methods. They were screened for their antimicrobial activity against Gram-positive and Gram-negative bacteria as well as for antifungal activity. The antimicrobial activity profile of the tested compounds showed some promising results. The potent activity of compounds 4d, 7b (117% zone inhibition) and 7c (105% zone inhibition) against Salmonella sp., exceeding that of the reference drug Gentamycin is particularly noteworthy. In general, the newly synthesized thiazolylphthalazine derivatives showed higher antimicrobial activity against the tested Gram-negative bacteria than against Gram-positive bacteria and fungi. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety
Molecules 2017, 22(1), 64; doi:10.3390/molecules22010064
Received: 21 November 2016 / Revised: 22 December 2016 / Accepted: 27 December 2016 / Published: 31 December 2016
Cited by 1 | PDF Full-text (2820 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities
[...] Read more.
Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-15I-7 exerted remarkably higher activities with EC50 values ranging from 0.45–1.86 μg/mL against X. oryzae and 1.97–20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle New Thiazolyl-triazole Schiff Bases: Synthesis and Evaluation of the Anti-Candida Potential
Molecules 2016, 21(11), 1595; doi:10.3390/molecules21111595
Received: 31 October 2016 / Revised: 14 November 2016 / Accepted: 17 November 2016 / Published: 22 November 2016
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Abstract
In the context of the dangerous phenomenon of fungal resistance to the available therapies, we present here the chemical synthesis of a new series of thiazolyl-triazole Schiff bases B1B15, which were in vitro assessed for their anti-Candida potential. Compound
[...] Read more.
In the context of the dangerous phenomenon of fungal resistance to the available therapies, we present here the chemical synthesis of a new series of thiazolyl-triazole Schiff bases B1B15, which were in vitro assessed for their anti-Candida potential. Compound B10 was found to be more potent against Candida spp. when compared with the reference drugs Fluconazole and Ketoconazole. A docking study of the newly synthesized Schiff bases was performed, and results showed good binding affinity in the active site of co-crystallized Itraconazole-lanosterol 14α-demethylase isolated from Saccharomyces cerevisiae. An in silico ADMET (absorption, distribution, metabolism, excretion, toxicity) study was done in order to predict some pharmacokinetic and pharmacotoxicological properties. The Schiff bases showed good drug-like properties. The results of in vitro anti-Candida activity, a docking study and ADMET prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, B10, which can be further optimized as a lead compound. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle One Pot Single Step Synthesis and Biological Evaluation of Some Novel Bis(1,3,4-thiadiazole) Derivatives as Potential Cytotoxic Agents
Molecules 2016, 21(11), 1532; doi:10.3390/molecules21111532
Received: 11 October 2016 / Revised: 5 November 2016 / Accepted: 9 November 2016 / Published: 15 November 2016
Cited by 10 | PDF Full-text (2693 KB) | HTML Full-text | XML Full-text
Abstract
A novel series of bis(1,3,4-thiadiazole) derivatives were synthesized in one step methodology with good yields by condensation reaction between bis-hydrazonoyl chloride 1 and various reagents. The structures of the prepared compounds were confirmed by spectral data (IR, NMR, and MS), and
[...] Read more.
A novel series of bis(1,3,4-thiadiazole) derivatives were synthesized in one step methodology with good yields by condensation reaction between bis-hydrazonoyl chloride 1 and various reagents. The structures of the prepared compounds were confirmed by spectral data (IR, NMR, and MS), and elemental analysis. The anticancer activity against human breast carcinoma (MCF-7) cancer cell lines was evaluated in MTT assay. The results revealed that the bis-thiadiazole derivatives 5c,d, 7b,c and 9c had higher antitumor activity than the standard drug Imatinib. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle Synthesis and Evaluation of New 1,3,4-Thiadiazole Derivatives as Antinociceptive Agents
Molecules 2016, 21(8), 1004; doi:10.3390/molecules21081004
Received: 24 June 2016 / Revised: 26 July 2016 / Accepted: 28 July 2016 / Published: 1 August 2016
Cited by 5 | PDF Full-text (2402 KB) | HTML Full-text | XML Full-text
Abstract
In the current work, new 1,3,4-thiadiazole derivatives were synthesized and investigated for their antinociceptive effects on nociceptive pathways of nervous system. The effects of these compounds against mechanical, thermal and chemical stimuli were evaluated by tail-clip, hot-plate and acetic acid-induced writhing tests, respectively.
[...] Read more.
In the current work, new 1,3,4-thiadiazole derivatives were synthesized and investigated for their antinociceptive effects on nociceptive pathways of nervous system. The effects of these compounds against mechanical, thermal and chemical stimuli were evaluated by tail-clip, hot-plate and acetic acid-induced writhing tests, respectively. In addition, activity cage was performed to assess the locomotor activity of animals. The obtained data indicated that compounds 3b, 3c, 3d, 3e, 3g and 3h increased the reaction times of mice both in the hot-plate and tail-clip tests, indicating the centrally mediated antinociceptive activity of these compounds. Additionally, the number of writhing behavior was significantly decreased by the administration of compounds 3a, 3c, 3e and 3f, which pointed out the peripherally mediated antinociceptive activity induced by these four compounds. According to the activity cage tests, compounds 3a, 3c and 3f significantly decreased both horizontal and vertical locomotor activity of mice. Antinociceptive behavior of these three compounds may be non-specific and caused by possible sedative effect or motor impairments. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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Open AccessArticle Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties
Molecules 2016, 21(5), 596; doi:10.3390/molecules21050596
Received: 28 March 2016 / Revised: 20 April 2016 / Accepted: 29 April 2016 / Published: 6 May 2016
Cited by 2 | PDF Full-text (2307 KB) | HTML Full-text | XML Full-text
Abstract
A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S2Cl2 and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, cyclohexadienone, cyclopentadiene, and benzoannulene, were
[...] Read more.
A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S2Cl2 and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, cyclohexadienone, cyclopentadiene, and benzoannulene, were selectively obtained in low to high yields. In most cases, the hetero ring-closure was accompanied by chlorination of the carbocyclic moieties. With naphthalenone derivatives, a novel dithiazole rearrangement (15→13) featuring unexpected movement of the dithiazole ring from α- to β-position, with respect to keto group, was discovered. Molecular structure of 4-chloro-5H-naphtho[1,2-d][1,2,3]dithiazol-5-one 13 was confirmed by single-crystal X-ray diffraction. Electrochemical properties of 13 were studied by cyclic voltammetry and a complex behavior was observed, most likely including hydrodechlorination at a low potential. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
Open AccessArticle Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi-Target Directed Ligands of Ser/Thr Kinases
Molecules 2016, 21(5), 578; doi:10.3390/molecules21050578
Received: 7 April 2016 / Revised: 22 April 2016 / Accepted: 23 April 2016 / Published: 30 April 2016
Cited by 4 | PDF Full-text (4561 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate
[...] Read more.
A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate (1) has been reinvestigated and performed on a multigram scale. The inhibitory potency of the final products against five kinases involved in Alzheimer’s disease was evaluated. This study demonstrates that some molecules of the 12 and 13 series described in this paper are particularly promising for the development of new multi-target inhibitors of kinases. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
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