Sulfamic Acid and Its N- and O-Substituted Derivatives

Spillane, William J.; Malaubier, Jean‐Baptiste

doi:10.1021/cr400230c

Cited by 107 publications

(75 citation statements)

References 921 publications

(1,319 reference statements)

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“…Decreasing carbohydrate intake is a major public health issue so when a high-potency sweetener is identified, it is common to search for structural analogs with similar, or even more interesting, properties [19][20][21]. In general, chemical synthesis is involved in generating these analogs by making slight modifications to the stereochemistry or substituents of the sweetener [22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners

Marchal

Génin

Waffo-Téguo³

et al. 2015

Analytica Chimica Acta

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Section: Introductionmentioning

confidence: 99%

Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners

Marchal

Génin

Waffo-Téguo³

et al. 2015

Analytica Chimica Acta

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“…Another hydrophilic tubular cavity is formed by the approach of the orientation of six heterocyclic parts of the anions. This particular arrangement is [24]) and longer toward those in sulfonamide (about 1.60 Å see Ref. [25]).…”

Section: Molecular Structurementioning

confidence: 75%

Crystal structure and thermal behaviors of the tetrapotassium salt of octahydroimidazo-[4,5-d]imidazol-1,3,4,6-tetrasulfonic acid (TACOS-K)

Zeman

Růžička

Moncóľ

et al. 2016

J Therm Anal Calorim

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The tetrahydrate of the tetrapotassium salt of octahydroimidazo- [4,5-d]imidazol-1,3,4,6-tetrasulfonic acid (TACOS-K), an new energetic material, was investigated in terms of its crystal structure, heat of combustion, thermal stability and decomposition kinetics. Its heat of combustion is -5487 ± 96 J g -1 from which a heat of formation of -3150 kJ mol -1 was estimated. It has been found that this compound has a hexagonal crystal space group with a density of 2.026 g mol -1 at 150 K. The organic anionic skeleton of the TACOS-K molecule is distinctly deformed. Six tetraanions interconnected by coordination to the potassium cations and hydrogen bridges to water molecules form hydrophilic as well as hydrophobic cavities. As an intermediate to synthesize cis-1,3,4,6-tetranitro-octahydroimidazo-[4,5-d]imidazole, it decomposes at around 31°C with a first peak temperature range of 46.6-94.3°C due to loss of water, depending on the heating rates. Hydrolysis of the N-S bonds might play an important role here. Crystalline water evaporation competes with this hydrolysis. TACOS-K has a residual mass of about 46 % at 2°C min -1 , which increases with the heating rate. Peak of the exothermic process occurs at 235.6°C at the same heating rate with an enthalpy change of 164 J g -1 . Dehydration occurs with an energy barrier of 36.7 kJ mol -1 followed by a shoulder mass loss process with a much higher activation energy 110.6 kJ mol -1 , while the activation energy for the main exothermic reaction is about 136.2 kJ mol -1 .

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“…Sulfamate derivatives have been known for several years as artifi cial sweeteners (cyclamates) [1], but therapeutic applications are numerous and have signifi cantly broadened in recent years [2,3]. They were fi rst known as anticonvulsants and the drug topimarate, discovered in 1980, is still used in clinical settings for the treatment of refractory epilepsy [4].…”

Section: Introductionmentioning

confidence: 99%

“…This could explain the high oral availability of these drugs since they were shown to bind reversibly to CA II in red blood cells, which allows them to avoid degradation in the liver. This property could lead to new therapeutic approaches against cancer because CA IX and CA XII are highly expressed in tumours which need them to maintain pH and eliminate CO 2 .…”

Section: Introductionmentioning

confidence: 99%

A Sequential Dual Cleavage of the Arylsulfamate Linker to Provide Both Sulfamate and Phenol Derivatives

Fournier¹,

Ciobanu²,

Poirier³

2015

ChemJMold

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Abstract. Tyramine sulfamate was linked to the trityl chloride resin and this polymeric solid support used to introduce two levels of molecular diversity by formation of peptide bonds. A dual cleavage strategy next generated in a sequential way (without resin split) two different types of compounds (phenol and arylsulfamate derivatives), which are therapeutically attractive types of compounds. Here, we used tyramine as a general scaffold, but other arylsulfamate derivatives could be judiciously used to extend the nature of synthesized compounds.

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Sulfamic Acid and Its N- and O-Substituted Derivatives

Cited by 107 publications

References 921 publications

Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners

Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners

Crystal structure and thermal behaviors of the tetrapotassium salt of octahydroimidazo-[4,5-d]imidazol-1,3,4,6-tetrasulfonic acid (TACOS-K)

A Sequential Dual Cleavage of the Arylsulfamate Linker to Provide Both Sulfamate and Phenol Derivatives

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