SO2‐Extrusion of an 8‐thiabicylo[3.2.1]octa‐2,6‐diene 8,8‐dioxide and rearrangement of the resulting cycloheptatriene

Takayama, Jun; Sugihara, Yoshiaki; Nakayama, Juzo

doi:10.1002/hc.20079

Cited by 10 publications

(2 citation statements)

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“…The existence of toluidides and xylidides 1а – h in the 4-ОН form is confirmed by the fact that noneof them are subjected to the primary elimination of SO 2 under the influence of electron impact ionization. This is quite a specific process, which is common for many cyclic sulfoderivatives [ 22 , 23 ]. In the case of 4-hydroxy-2,2-dioxo-1 H -2λ 6 ,1-benzothiazine-3-carboxamides, it is characteristic only for those compounds that exist in the form of internal salts (4-olates) [ 14 , 16 ].…”

Section: Resultsmentioning

confidence: 99%

The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides

et al. 2016

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In continuing the search for new analgesics among derivatives of 2,1-benzothiazines, a series of corresponding toluidides and xylidides of 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic acid has been synthesized by the reaction of ethyl 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate with equimolar amounts of mono- and dimethyl-substituted anilides in boiling dry xylene. Their structure has been confirmed by the data of elemental analysis, nuclear magnetic resonance (NMR) spectroscopy (1Н and 13С), as well as mass spectrometry. All compounds obtained were subjected to pharmacological screening to identify their analgesic properties. Testing was carried out in male rats using the standard model of the thermal tail-flick (tail immersion test) in parallel and in comparison with the structurally related drugs meloxicam and piroxicam. Among the substances studied, highly active oral painkillers have been found; they exceed the analgesic effect of the reference drugs using the same dose. Interesting structural and biological regularities have been described; they will be useful in further research on creating promising new analgesics based on 4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides.

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Section: Resultsmentioning

confidence: 99%

The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides

et al. 2016

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“…Îáðàùàåò íà ñåáÿ âíèìàíèå è òîò ôàêò, ÷òî èçó÷àåìûå ñîåäèíåíèÿ ïîä âîçäåéñòâèåì ýëåêòðîííîãî óäàðà íå ïîäâåðãàþòñÿ ïåðâè÷íîìó ýëèìèíèðîâàíèþ SO 2 . Ýòîò âåñüìà ñïåöè-ôè÷íûé è îáû÷íûé äëÿ öèêëè÷åñêèõ ñóëüôàìèäîâ ïðîöåññ [11,12] Ò à á ë è ö à 2 Ñïåêòðû ßÌÐ 1 Í àíèëèäîâ (IIà -í) + .…”

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Новый синтез, анальгетическая и диуретическая активность галогензамещенных анилидов 4-гидрокси-1-метил-2,2-диоксо-1H-2λ6,1-бензотиазин-3-карбоновой кислоты

Украинец¹,

Petrushova²,

Дзюбенко³

et al. 2016

Хим.-фарм. ж.

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Предложен новый способ получения N-арил-4-гидрокси-1-метил-2,2-диоксо-1H-2λ6,1-бензотиазин-3-карбоксамидов, отличающийся простотой исполнения и высокими выходами конечных продуктов. Синтезирована серия галогензамещенных производных, изучены их спектры ЯМР 1H и 13C, а также особенности масс-спектрометрических характеристик. Первичный фармакологический скрининг показал перспективу создания на основе исследуемого класса соединений потенциальных анальгетиков и диуретиков, подтвердив тем самым высокую эффективность методологии «flip-flop drugs».

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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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SO₂‐Extrusion of an 8‐thiabicylo[3.2.1]octa‐2,6‐diene 8,8‐dioxide and rearrangement of the resulting cycloheptatriene

Abstract: The

Cited by 10 publications

References 20 publications

The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides

The Study of Structure—Analgesic Activity Relationships in a Series of 4-Hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic Acid Toluidides and Xylidides

Новый синтез, анальгетическая и диуретическая активность галогензамещенных анилидов 4-гидрокси-1-метил-2,2-диоксо-1<I>H</I>-2λ<sup>6</sup>,1-бензотиазин-3-карбоновой кислоты

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

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