Synthesis of Sydnones and Sydnone Imines

Greco, C. V.; Nyberg, Wayne H.; Cheng, C. C.

doi:10.1021/jm01239a022

Cited by 37 publications

(11 citation statements)

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“…A number of mesoionic compounds have also been examined in the search for anticancer agents [7–9]. Recently, Grynberg et al [10]synthesized a new one, the 4‐phenyl‐5‐(4‐nitro‐cinnamoyl)‐1,3,4‐thiadiazolium‐2‐phenylamine chloride (MI‐D; Fig.…”

Section: Introductionmentioning

confidence: 99%

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

et al. 1998

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MI-D (4-phenyl-5-(4-nitro-cinnamoyl)-1,3,4-thiadiazolium-2-phenylamine chloride), a new mesoionic compound, depressed the phosphorylation efficiency of liver mitochondria as deduced from an accentuated decrease of the respiratory control coefficient and ADP/O ratio. Analysis of segments of the respiratory chain suggested that the MI-D inhibition site is further on than complex I and between complexes II and III. The transmembrane electrical potential (v vi i) was collapsed dependent on MI-D concentration. ATPase activity was dramatically increased by MI-D in intact mitochondria, but inhibited in carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP)-uncoupled mitochondria. These results suggest that MI-D acts as an uncoupler agent, a property closely related to its structural characteristics.z 1998 Federation of European Biochemical Societies.

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Section: Introductionmentioning

confidence: 99%

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

et al. 1998

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“…18 MHz on a Bruker WPIOO spectrometer. DEPT-experiments were carried out to identify different orders of carbon signals.…”

Section: Resultsmentioning

confidence: 99%

“…18 MHz. Solutions of sample in deuterochloroformor <4-dimethyIsulfoxide were prepared in tubes of S mm o.d.…”

Section: Methodsmentioning

confidence: 99%

Carbon‐13 NMR Studies of 3‐Aryl‐4‐(5‐aryl‐Δ ²‐1,2,4‐oxadiazolin‐3‐yl)sydnones and 3‐Aryl‐4‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)sydnones

Huang

Yeh

1991

J Chinese Chemical Soc

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The 13C NMR spectra of twelve 3‐aryl‐4‐(5‐aryl‐Δ2‐l,2,4‐oxadiazolin‐3‐yl)sydnones and twelve 3‐aryl‐4‐(5‐aryl‐l,2,4‐oxadiazol‐3‐yl)sydnones have been measured and assigned by means of proton‐noise decoupling and DEPT‐experiments. The coupling constants were determined by means of gated decoupling, and NOE effects were observed by comparison of proton‐decoupled and inverse‐gated decoupled spectra. Differences shown by the oxadiazoline and the oxadiazole rings and the substitution effects are discussed.

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“…Hydrolysis of the ester (II) gave the dicarboxylic acid (I), while hydrazinolysis of the ester (B) gave the dicarbohyrazide (IV). The sydnone precursors (A) were all prepared from the corresponding anilines via the substituted N-aryl-Nnitrosoglycines (Greco et al, 1962;Fun et al, 2010).…”

Section: Chemical Contextmentioning

confidence: 99%

Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives: synthesis, molecular conformation and hydrogen bonding

et al. 2018

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1-Phenyl-1H-pyrazole-3,4-dicarboxylic acid and 1-(4-methoxyphenyl)-1H-pyrazole-3,4-dicarbohydrazide form complex hydrogen-bonded framework structures each containing multiple hydrogen-bond types, but dimethyl 1-phenyl-1H-pyrazole-3,4-dicarboxylate and dimethyl 1-(4-methylphenyl)-1H-pyrazole-3,4-dicarboxylate form simple cyclic dimers containing only C—H⋯O hydrogen bonds.

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Synthesis of Sydnones and Sydnone Imines

Cited by 37 publications

References 2 publications

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

Carbon‐13 NMR Studies of 3‐Aryl‐4‐(5‐aryl‐Δ ²‐1,2,4‐oxadiazolin‐3‐yl)sydnones and 3‐Aryl‐4‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)sydnones

Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives: synthesis, molecular conformation and hydrogen bonding

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Synthesis of Sydnones and Sydnone Imines

Cited by 37 publications

References 2 publications

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

Effect of MI‐D, a new mesoionic compound, on energy‐linked functions of rat liver mitochondria

Carbon‐13 NMR Studies of 3‐Aryl‐4‐(5‐aryl‐Δ 2‐1,2,4‐oxadiazolin‐3‐yl)sydnones and 3‐Aryl‐4‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)sydnones

Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives: synthesis, molecular conformation and hydrogen bonding

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Carbon‐13 NMR Studies of 3‐Aryl‐4‐(5‐aryl‐Δ ²‐1,2,4‐oxadiazolin‐3‐yl)sydnones and 3‐Aryl‐4‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)sydnones