Synthese von 1,2‐Thiazinen und 1,2‐Thiazepinen durch Ringerweiterung

Stachel, Hans‐Dietrich; Poschenrie, Hermann; Lomitzky, Viktor

doi:10.1002/ardp.19923250803

Cited by 10 publications

(3 citation statements)

References 10 publications

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“…Finally, worth noting the Lewis acid-catalyzed rearrangement reactions accompanied by the ring expansion. The substrates for these reactions are δ-sultams possessing annelated or spirosubstituted three-membered heterocycle (Scheme 1, G [57] and H [58,59]).…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Milokhov,

Pomalin,

Balabushko

et al. 2023

Preprint

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In this article, we designed and synthesized a series of novel 2,5,5-trisubstituted (including spirocyclic) 1,2-thiazepan-6-one 1,1-dioxides (put simply, γ,γ-disubstituted β-keto ε-sultams), prepared a number of derivatives and evaluated their cytotoxic activity against MDA-MB-231 breast cancer cell line. In particular, alkylation of N-monosubstituted methanesulfonamides with α,α-disubstituted β-halogenated esters (including cyclic representatives) afforded the corresponding N-mesylated β-amino acid esters. The latters were involved in CSIC (Carbanion-mediated Sulfonamide Intramolecular Cyclization) reaction to give the target γ,γ-disubstituted β-keto ε-sultams (including spirocyclic representatives) in synthetically useful yields. This class of compounds can be considered as valuable building blocks since they possess carbonyl functionality and an EWG-activated methylene group capable of further functionalization. For instance, the condensation with DMFDMA afforded the corresponding α-dimethylaminomethylidene derivatives ‒ the direct precursors for the heterocyclization reactions. Their treatment with hydrazine hydrate or guanidine hydrochloride provided the corresponding pyrazolo- and pyrimidofused ε-sultams. Despite the prepared β-keto ε-sultams showing weak cytotoxicity against the MDA-MB-231 breast cancer cell line, their pyrazolofused derivatives appeared perspective pharmacological templates with stable cytotoxic effects. Moreover, β-keto ε-sultams and their heterofused derivatives form the water-soluble conjugates with branched polymers based on dextran-polyacrylamide (D-PAA) that can be used as the transport module for the targeted drug delivery in biological media.

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Section: Chemistrymentioning

confidence: 99%

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Milokhov,

Pomalin,

Balabushko

et al. 2023

Preprint

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“…There are a few examples of spiroepoxides being turned into cyclic carbonyl compounds by Brønsted or Lewis acids [12,[14][15][16][17][18] . The isomerization proceeds via a 1,2-shift and ensuing electrophilic ring opening.…”

Section: Chemistrymentioning

confidence: 99%

Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure

Poschenrieder¹,

Höfner²,

Stachel³

2000

Arch. Pharm. Pharm. Med. Chem.

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A series of piperidine‐2,3,5‐triones (azagrevellins) has been prepared. A new synthesis has been introduced using the rearrangement of spiroepoxides in the presence of triethyloxonium tetrafluoroborate. The binding affinity toward the N‐methyl‐D‐aspartate (glycine site) receptor has been measured to provide a basis for more detailed structure‐activity studies. Azagrevellin 18d showed the highest binding potency.

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“…[7] As well, the tandem reaction consisting in addition of N-methylmethanesulfonamide to ethyl 3-phenylpropionate followed by intramolecular condensation gave the appropriately substituted thiazine-5-one (Figure 2). [8] An alternative synthetic pathway to fused ketosultams, the PPA (polyphosphoric acid)mediated cyclization of (arylamino)sulfonyl acetic acid was demonstrated by a single example. [9] At the same time, sp 3 -enriched β-keto-δ-sultams were synthesized trough either a formal Diels-Alder reaction between sulfonylamine and activated diene [10] or the intramolecular Michael-type cyclization of substituted 2-oxo-3butene-1-sulfonamide (Figure 2).…”

mentioning

confidence: 99%

Synthesis of 4,4‐Disubstituted 1,2‐Thiazinane‐5‐one 1,1‐Dioxides via the CSIC^[≠]Reaction Strategy

et al. 2020

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A series of sp3‐enriched 2,2‐disubstituted 1,2‐thiazinane‐5‐one 1,1‐dioxides (including spirocyclic derivatives) has been synthesized through the CSIC [Carbanion mediated Sulfonate (Sulfonamido) Intramolecular Cyclization] reaction strategy. In particular, 2,2‐disubstituted alkyl 3‐aminopropanoates were subsequently sulfonylated with mesyl chloride followed by alkylation with methyl iodide to give the key precursor 2,2‐disubstituted methyl 3‐(methylsulfonamido)propanoates. The latter were treated with sodium hydride and underwent the intramolecular sulfa‐Dieckmann cyclization yielding the target 4,4‐disubstituted 1,2‐thiazinane‐5‐one 1,1‐dioxides (so‐called β‐keto‐δ‐sultams). The structure of the target compounds was confirmed by an X‐ray diffraction study.

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Synthese von 1,2‐Thiazinen und 1,2‐Thiazepinen durch Ringerweiterung

Cited by 10 publications

References 10 publications

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure

Synthesis of 4,4‐Disubstituted 1,2‐Thiazinane‐5‐one 1,1‐Dioxides via the CSIC^[≠]Reaction Strategy

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Synthese von 1,2‐Thiazinen und 1,2‐Thiazepinen durch Ringerweiterung

Cited by 10 publications

References 10 publications

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Design, synthesis, chemical and biological evaluation of 2,5,5-trisubstituted-1,2-thiazepan-6-one 1,1-dioxides

Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure

Synthesis of 4,4‐Disubstituted 1,2‐Thiazinane‐5‐one 1,1‐Dioxides via the CSIC[≠]Reaction Strategy

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Synthesis of 4,4‐Disubstituted 1,2‐Thiazinane‐5‐one 1,1‐Dioxides via the CSIC^[≠]Reaction Strategy