Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework

Hys, Vasyl Y.; Milokhov, Demyd S.; Volovenko, Olesya; Konovalova, Irina S.; Shishkina, Svitlana V.; Volovenko, Yulian M.

doi:10.1055/s-0040-1707405

Cited by 10 publications

(3 citation statements)

References 11 publications

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“…Recently we have reported the synthesis of carbo-and heterofused 7-membered (aza)sultams [60][61][62] trough the CSIС (Carbanion-mediated Sulfonate (Sulfonamide) Intermolecular Coupling (Intramolecular Cyclization)) [63][64][65][66][67][68] reaction strategy. In present work we applied this strategy toward the synthesis of sp 3 -enriched ε-sultams.…”

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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“…To date, only a single compound bearing the pyrazolothiadiazepine scaffold as part of a tricyclic structure has been reported. [9] In the literature, two main approaches for constructing the pyrazolothiadizine skeleton have been described.…”

Section: Introductionmentioning

confidence: 99%

“…Its limited visibility can be primarily attributed to the absence of convenient and broadly applicable synthetic methods. To date, only a single compound bearing the pyrazolothiadiazepine scaffold as part of a tricyclic structure has been reported [9] …”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Fused Heterocycles Incorporating Pyrazole/Thiadiazine or Pyrazole/Thiadiazepine Fragments Using N‐Chlorosulfonyltrihaloacetimidoyl Chlorides

Shalimov,

Kolotylo,

Otsaliuk

et al. 2023

ChemistrySelect

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A novel simple and effective method has been developed for constructing pyrazolothiadiazine and pyrazolothiadiazepine fused heterocycles incorporating an endocyclic sulfonamide fragment. The cyclocondensation of readily available N‐(chlorosulfonyl)imidoyl chlorides, RC(Cl)=NSO2Cl (R=CCl3, CF2Br), with N‐methyl‐substituted 4‐ or 5‐aminopyrazoles results in the formation of isomeric pyrazolothiadiazine‐S,S‐dioxides. Additionally, when 5‐ or 3‐aminoalkyl‐substituted pyrazoles are employed, they serve as 1,4‐N−C−C−C binucleophiles, leading to the synthesis of novel pyrazolothiadiazepine heterocycles. Notably, the trichloromethyl and bromodifluoromethyl substituents in these compounds can be converted into dichloromethyl and difluoromethyl groups, providing enhanced functionalization options.

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Updating the CSIC Reaction (2003–2020)

Dobrydnev

Marco‐Contelles

2021

Eur J Org Chem

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Herein, we have updated the progress and developments of the Carbanion-mediated Sulfonate (or Sulfonamide) Intermolecular Coupling, and Intramolecular Cyclization, abbreviated as CSIC reaction (CSICr), in the last seventeen years from the seminal review published in 2003 in this same Journal. CSICr has proven to be a useful and versatile synthetic tool, efficiently providing a number of open-chain [alkane(sulfonamide)sulfonates] or cylic (sultams and sultones) synthetic intermediates or final products of high value in organic and medicinal chemistry.

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Synthetic Approach to Fused Azasultams with 1,2,4-Thiadiazepine Framework

Cited by 10 publications

References 11 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

Efficient Synthesis of Fused Heterocycles Incorporating Pyrazole/Thiadiazine or Pyrazole/Thiadiazepine Fragments Using N‐Chlorosulfonyltrihaloacetimidoyl Chlorides

Updating the CSIC Reaction (2003–2020)

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