The Chemistry of Bioactive Mesoionic Heterocycles

Kawase, Masami; Sakagami, Hiroshi; Motohashi, Noboru

doi:10.1007/7081_2007_096

Cited by 25 publications

(14 citation statements)

References 77 publications

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“…Mesoionic compounds are planar five-membered ring betaines, which contain distinct regions of positive and negative charges associated with any poly-heteroatomic system, yet have a net neutral electrical character. These properties enable them to cross cellular membranes and interact strongly with biomolecules [ 24 ]. Hydrochlorides of the mesoionic compounds MC-1 and MC-2 effectively enhanced the antibiotic activity of tetracycline and erythromycin by reducing the concentrations needed to inhibit the growth of drug resistant (effluxing) strains.…”

Section: Resultsmentioning

confidence: 99%

Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds

et al. 2011

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Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 μg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold.

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Section: Resultsmentioning

confidence: 99%

Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds

et al. 2011

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“…The class of compounds based on an indole scaffold is of immense chemical and biological significance [1,2]. Among the nitrogen containing heterocycles, indole is the parent core in a large number of naturally occurring bioactive compounds.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis

et al. 2019

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The crystal structures of five new chalcones derived from N-ethyl-3-acetylindole with different substituents were investigated: (E)-3-(4-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3a); (E)-3-(3-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3b); (E)-1-(1-ethyl-1H-indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one (3c); (E)-1-(1-ethyl-1H-indol-3-yl)-3-mesitylprop-2-en-1-one (3d); and (E)-1-(1-ethyl-1H-indol-3-yl)-3-(furan-2-yl)prop-2-en-1-one (3e). The molecular packing of the studied compounds is controlled mainly by C–H⋅⋅⋅O hydrogen bonds, C–H⋅⋅⋅π interactions, and π···π stacking interactions, which were quantitatively analyzed using Hirshfeld topology analysis. Using density functional theory (DFT) calculations, the order of polarity (3b ˂ 3d ˂ 3e ˂ 3a ˂ 3c) was determined. Several chemical reactivity indices such as the ionization potential (I), electron affinity (A), chemical potential (μ), hardness (η), electrophilicity (ω) and nucleophilicity (N) indices were calculated, and these properties are discussed and compared. In addition, the antiproliferative activity of the five new chalcones was studied.

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“…The 1,2,4-triazolium-3-aminides II and III belong to the family of mesoionic five-membered heterocycles, of which the sydnones (1,2,3-oxadiazolium-5-olates), sydnone imines (1,2,3-oxadiazolium-5-aminides), and 1,3,4-thiadiazolium derived mesoionics are perhaps the best known members [25–26]. While not much is known about congeners of II , diverse biological activities have been reported for some of the other types of mesoionic heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

Szabo

Greiner

Maas

2017

Beilstein J. Org. Chem.

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Depending on the reaction conditions, N,N’,N’’-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N,N’,N’’-tris(N-acyl-N-benzylamido)guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.

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The Chemistry of Bioactive Mesoionic Heterocycles

Cited by 25 publications

References 77 publications

Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds

Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds

Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

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