Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

Borst, Mark L.G.; Ouairy, Cécile; Fokkema, Sander C.; Cecchi, Alessandro; Kerckhoffs, Jessica M. C. A.; Boer, Vincent L. de; Boogaard, Peter J.; Bus, Rutger F.; Ebens, Rijko; Hulst, Rob van der; Knol, Joop; Libbers, Rob; Lion, Zhou M.; Settels, Bart W.; Wever, Ellen de; Attia, Khaled A.; Sinnema, Piet-Jan; Gooijer, Jesse M. de; Harkema, Karen; Hazewinkel, Marieke; Snijder, Susan; Pouwer, Kees

doi:10.1021/acscombsci.7b00150

Cited by 25 publications

(15 citation statements)

References 35 publications

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“…The double displacement cyclic thioetherification strategy was also utilized for the synthesis of thietane-containing spironucleosides. The easily available 5-aldo-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (36) was first treated with formaldehyde in the presence of NaOH followed by MsCl, affording the dimesylate derivative 38, which was reacted with Na 2 S to afford the spirothietane 39. The latter was further converted into the thietane-containing spironucleoside 40 [40] (Scheme 8).…”

Section: Methodsmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

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Section: Methodsmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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“…18 In the Scheme 7 are reported selected examples of these new structural motifs that are of interest in drug discovery as 3D mimics of aromatic rings. 19 It is worth mentioning that the optimal reaction conditions required a large excess of the oxidant (3 equiv. of PIDA) and 2 equiv.…”

Section: Oxo-imination Of Sulfides: Synthesis Of Sulfoximinesmentioning

confidence: 99%

Hypervalent iodine (III) reagents and ammonia as useful combination for highly chemoselective N-transfer to low-valent organosulfur compounds and amines

Liuisi¹,

Andresini²,

Colella³

et al. 2021

Arkivoc

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The combination of hypervalent iodine (III) reagents and source of ammonia allows the genesis of iodonitrene species able to act as source of electrophilic nitrogen. Ammonia umpolung represents the net-result of this combination. Since the introduction of this method in 2016, important and unprecedented transformations have been discovered. In this short review we report the state of the art in the use of this type of iodonitrene in modern synthesis.

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“…Full experimental details and analytical data ( 1 H NMR, 13 C NMR, X-ray analysis) are provided in the Supporting Information (SI).…”

Section: Standard Procedures For N-arylation Of Bcp-sulfoximinesmentioning

confidence: 99%

“…Overall, the replacement of other sulfur‐based functional groups by sulfoximines can have positive effects on physicochemical properties and metabolic stability . Recently, polycyclic sulfoximines gained interest for their 3D scaffold and easy diversification …”

Section: Introductionmentioning

confidence: 99%

“…[12] Recently, polycyclic sulfoximines gained interest for their 3D scaffold and easy diversification. [13] After early syntheses of sulfoximines from sulfoxides with hydrazoic acid, [14] the available methods underwent significant improvements. [15] Unprotected sulfoximines can be synthesized from sulfoxides involving a transition-metal catalyst [16] or metal-free using ammonium carbamate.…”

Section: Introductionmentioning

confidence: 99%

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Bicyclo[1.1.1]pentyl Sulfoximines: Synthesis and Functionalizations

et al. 2020

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Herein we present the first synthesis of bicyclo[1.1.1]pentyl (BCP) sulfoximines from the corresponding sulfides. Both BCPs and sulfoximines are bioisosteres used in medicinal chemistry and therefore desirable motifs. The access to BCP sulfides was enabled by the thiol addition to [1.1.1]propellane as published before. A broad scope with specific limitations was discovered for the sulfoximination. To diversify the sulfoximines, N‐acylations and N‐arylations were performed. As the N‐arylation was low yielding we optimized the copper(I) catalyzed reaction. A wide range of aryl iodides could be deployed and competitive reactions showed that aryl bromides react equally fast. In a scale‐up we prepared a suitable precursor for a BCP drug analogue. In this work several molecular structures could be determined by single‐crystal X‐ray diffraction.

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Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

Cited by 25 publications

References 35 publications

Recent synthesis of thietanes

Recent synthesis of thietanes

Hypervalent iodine (III) reagents and ammonia as useful combination for highly chemoselective N-transfer to low-valent organosulfur compounds and amines

Bicyclo[1.1.1]pentyl Sulfoximines: Synthesis and Functionalizations

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