Selective di- and monochlorination of pyridazine-annelated bis(imidazolium) salts

2016 ◽  
Vol 71 (6) ◽  
pp. 659-666 ◽  
Author(s):  
Benjamin Raible ◽  
Doris Kunz
Keyword(s):  
Molecular Structure ◽  
Steric Hindrance ◽  
Acetyl Chloride ◽  
Synthetic Route ◽  
Imidazolium Salts ◽  
Imidazolium Salt ◽  
Trichloroisocyanuric Acid ◽  
The Ideal

AbstractA synthetic route for the selective di- and monochlorination of pyridazine annelated bis(imidazolium) salts at the formamidinium moieties with trichloroisocyanuric acid (TCCA) is presented. Due to the steric hindrance, the molecular structure of the dichlorobis(imidazolium) salt shows a pronounced torsion from planarity as well as a deviation of the C–Cl bond vectors from the ideal bisecting line of the respective NCN angles such as to avoid each other. The monochlorinated bis(imidazolium) salt is free of steric hindrance and therefore shows less deviation from the parent bis(imidazolium) salt. In the presence of acetate the chloroimidazolium salt acts as a chlorination agent for acetate leading to formation of acetyl chloride and the respective urea.

Intramolecular Diels Alder reactions in highly organized imidazolium salt-based ionic liquid crystals

RSC Advances ◽  
2015 ◽  
Vol 5 (1) ◽  
pp. 635-639 ◽  
Author(s):  
Tien Dat Do ◽  
Andreea R. Schmitzer
Keyword(s):  
Ionic Liquid ◽  
Liquid Crystals ◽  
Diels Alder ◽  
Imidazolium Salts ◽  
Imidazolium Salt ◽  
New Family ◽  
Ionic Liquid Crystals

This paper describes the development of a new family of ionic liquid crystals based on imidazolium salts and their applications as media for intramolecular Diels Alder reactions.

scholarly journals (3E)-5-Chloro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one

IUCrData ◽  
2016 ◽  
Vol 1 (2) ◽  
Author(s):  
Viviane C. D. Bittencourt ◽  
Roberta M. F. C. Almeida ◽  
Adailton J. Bortoluzzi ◽  
Vanessa C. Gervini ◽  
Adriano Bof de Oliveira
Keyword(s):  
Molecular Structure ◽  
Free Energy ◽  
Title Compound ◽  
In Silico ◽  
Intramolecular Interaction ◽  
Compound C ◽  
Centroid Distance ◽  
The Ideal

The reaction between 5-cholroisatin and phenylhydrazine yields the title compound, C14H10ClN3O. The molecular structure deviates slightly from the ideal planarity, with an r.m.s. deviation of 0.1372 (12) Å for the non-H atoms. An N—H...O intramolecular interaction is observed, which supports anEconformation with respect to the C=N bond. In the crystal, molecules are linked by a pair of N—H...O interactions into an inversion dimer. The dimers are linked by weak C—H...Cl interactions, formng a tape structure along [101]. The tapes are also linked through a weak π–π interaction [centroid–centroid distance = 3.5773 (8) Å] into a layer parallel to (-111). Anin silicoevaluation of the title compound with a topoisomerase enzyme was performed and the global free energy of −26.59 kJ mol−1was found.

Synthesis, Characterization, and Biological Activity of Anthraquinone-Substituted Imidazolium Salts for the Treatment of Bladder Cancer

2020 ◽  
Vol 6 (4) ◽  
pp. 471-479
Author(s):  
Michael L. Stromyer ◽  
David J. Weader ◽  
Uttam Satyal ◽  
Philip H. Abbosh ◽  
Wiley J. Youngs
Keyword(s):  
Bladder Cancer ◽  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
High Grade ◽  
Imidazolium Salts ◽  
Muscle Invasive Bladder Cancer ◽  
Imidazolium Salt ◽  
Muscle Invasive

BACKGROUND: Bladder cancer is one of the most common types of cancer diagnosed each year, and more than half of patients have non-muscle invasive bladder cancer (NMIBC). The standard of care for patients with high-grade NMIBC is Bacillus Calmette-Guerin (BCG). Unfortunately, multiple BCG shortages have limited access to this treatment. Available alternatives using intravesical administration of chemotherapy have some efficacy, but lack prospective validation and long-term outcomes. Development of novel intravesical therapies may provide more active alternatives to BCG for patients with high-grade NMIBC. OBJECTIVE: To develop an optimal imidazolium salt for the intravesical treatment of NMIBC and determine preliminary in vitro activity of anthraquinone-substituted imidazolium salts. METHODS: The development of the anthraquinone-substituted imidazolium salts was undertaken in an attempt to increase the potency of this class of compounds by incorporating the quinone functional group observed in the chemotherapeutics doxorubicin, valrubicin, and mitomycin. All compounds were characterized by 1H and 13C NMR spectroscopy and infrared spectroscopy. Furthermore, these imidazolium salts were tested for in vitro cytotoxicity by the Developmental Therapeutics Program (DTP) on the NCI-60 human tumor cell line screening. Additional in vitro testing was performed against diverse bladder cancer cell lines (RT112, TCCSUP, J82, and UMUC13) using CellTiter-Glo® assays and colony-forming assays. RESULTS: The NCI-60 cell line screening indicated that compound 7 had the highest activity and was concluded to be the optimal compound for further study. Using CellTiter-Glo® assays on bladder cancer cell lines, 50% growth inhibitory concentration (IC50) values were determined to range from 32–50μM after an exposure of 1 h, for compound 7. Further evaluation of the compound by colony-forming assays showed the complete inhibition of growth at 10 days post a 100μM dose of compound 7 for 1 h. CONCLUSIONS: The most active lipophilic anthraquinone imidazolium salt, compound 7, could be a viable treatment for non-muscle invasive bladder cancer as it exhibits a cell-killing effect at a 1 h time period and completely inhibits cancer regrowth in colony-forming assays.

Facile synthesis of functionalized urea, imidazolium salt, azide, and triazole from a 2-amino-5,7-dimethyl-1,8-naphthyridine scaffold and their utilization in fluoride ion sensing

2018 ◽  
Vol 42 (12) ◽  
pp. 10059-10066 ◽  
Author(s):  
Mandeep K. Chahal ◽  
Tawseef Ahmad Dar ◽  
Muniappan Sankar
Keyword(s):  
Selective Recognition ◽  
Fluoride Ion ◽  
Synthetic Route ◽  
Facile Synthesis ◽  
Imidazolium Salt ◽  
Ion Sensing

We report an elegant and modest synthetic route for the synthesis of four new 1,8-naphthyridine-based receptors (1a, 1b, 2, 3 and 4). Among them, 1a and 2 exhibit selective recognition of F− ions.

scholarly journals An efficient Pd–NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

2017 ◽  
Vol 13 ◽  
pp. 1735-1744 ◽  
Author(s):  
Nan Sun ◽  
Meng Chen ◽  
Liqun Jin ◽  
Wei Zhao ◽  
Baoxiang Hu ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Imidazole Ring ◽  
Catalyst System ◽  
Water Soluble ◽  
Imidazolium Salts ◽  
Heck Reactions ◽  
Imidazolium Salt ◽  
Simple Method ◽  
Wide Range

Three PEG-functionalized imidazolium salts L1–L3 were designed and prepared from commercially available materials via a simple method. Their corresponding water soluble Pd–NHC catalysts, in situ generated from the imidazolium salts L1–L3 and Na2PdCl4 in water, showed impressive catalytic activity for aqueous Mizoroki–Heck reactions. The kinetic study revealed that the Pd catalyst derived from the imidazolium salt L1, bearing a pyridine-2-methyl substituent at the N3 atom of the imidazole ring, showed the best catalytic activity. Under the optimal conditions, a wide range of substituted alkenes were achieved in good to excellent yields from various aryl bromides and alkenes with the catalyst TON of up to 10,000.

scholarly journals Scalable Synthesis of 1,3,4,5-Tetraaryl Imidazolium Salts as Precursors of Sterically Demanding N-Heterocyclic Carbenes

SynOpen ◽  
2020 ◽  
Vol 04 (01) ◽  
pp. 01-11
Author(s):  
Cengiz Azap ◽  
Anna Christoffers ◽  
Renat Kadyrov
Keyword(s):  
Large Scale ◽  
Oxidative Desulfurization ◽  
Heterocyclic Carbenes ◽  
Imidazolium Salts ◽  
Imidazolium Salt ◽  
Available N ◽  
Sterically Demanding ◽  
Cost Efficient ◽  
Scalable Synthesis ◽  
Electron Donation

A convenient, large-scale, and cost-efficient synthesis of 4,5-diarylsubstituted N,N-diarylimidazolium salts is described. A variety of 1,3,4,5-tetraaryl imidazolium salts with increasing electron donation and steric bulk of the N-aryl groups was synthesized in good yields. In the key step, readily available N,N′-diarylthioureas and benzoin/anisoin are coupled to give imidazole-2-thiones, followed by imidazolium salt formation by oxidative desulfurization. In this way, N,N-diarylimidazolium salts with 2-methoxy, 2-methyl, and 2-isopropyl substituents could be obtained; the synthesis of their 2-tert-butyl, 2,6-dimethyl, and 2,6-diisopropyl analogues failed.

scholarly journals Microbiota potentialized larvicidal action of imidazolium salts against Aedes aegypti (Diptera: Culicidae)

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Harry Luiz Pilz-Junior ◽  
Alessandra Bittencourt de Lemos ◽  
Kauana Nunes de Almeida ◽  
Gertrudes Corção ◽  
Henri Stephan Schrekker ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Molecular Markers ◽  
Aedes Aegypti ◽  
Bacterial Communities ◽  
Blood Feeding ◽  
Imidazolium Salts ◽  
Imidazolium Salt ◽  
Chemical Products ◽  
Laboratory Breeding

Abstract Mosquitoes are important vectors of pathogens due to their blood feeding behavior. Aedes aegypti (Diptera: Culicidae) transmits arboviruses, such as dengue, Zika, and Chikungunya. This species carries several bacteria that may be beneficial for its biological and physiological development. Therefore, studying the response of its microbiota to chemical products could result in vector control. Recently, imidazolium salts (IS) were identified as effective Ae. aegypti larvicides. Considering the importance of the mosquito microbiota, this study addressed the influence of IS on the bacteria of Ae. aegypti larvae. After exposition of larvae to different IS concentrations, the cultured microbiota was identified through culturomics and mass spectrometry, and the non-cultivated microbiota was characterized by molecular markers. In addition, the influence of the IS on axenic larvae was studied for comparison. There was an alteration in both cultivable species and in their diversity, including modifications in bacterial communities. The axenic larvae were less susceptible to the IS, which was increased after exposing these larvae to bacteria of laboratory breeding water. This highlights the importance of understanding the role of the larval microbiota of Ae. aegypti in the development of imidazolium salt-based larvicides. Such effect of IS towards microbiota of Ae. aegypti larvae, through their antimicrobial action, increases their larvicidal potential.

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