Synthesis of sulfonimidamides from sulfinamides by oxidation with <i>N</i>-chlorosuccinimide

Mancheño, Olga Garcı́a; Bolm, Carsten

doi:10.1186/1860-5397-3-25

Cited by 39 publications

(17 citation statements)

References 23 publications

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“…The sulfonimidamides (i.e., 1 ), which are not commercially available, were prepared according to literature procedures 12f,13. Our studies began with the reaction of sulfonimidamide 1a (3.0 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

et al. 2015

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We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The reaction leads to hitherto unknown N‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised N‐alkynylated sulfonimidamides could undergo silica‐gel‐mediated hydrolysis to give the corresponding N‐acyl‐sulfonimidamides, as well as borane–dimethyl sulfide‐mediated reduction to give the corresponding N‐alkylated sulfonimidamides.

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Section: Resultsmentioning

confidence: 99%

Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

et al. 2015

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“…All attempts to use ammonia (in aqueous, concentrated, diluted, or gaseous form) remained unsuccessful, and degradation of compound 8 occurred. Finally, hexamethyldisilazane proved to be a suitable NH 2 equivalent [72], and in this manner, tasisulam analog 2 was obtained in 78% yield. The NMR spectroscopic data suggested the depicted (racemic) tautomeric structure for compound 2.…”

Section: Resultsmentioning

confidence: 99%

“…With respect to applications of sulfonimidamides as reagents in synthesis and catalysis, the early work by the groups of Malacria [61,62,63] and Dodd [64,65,66,67] is noteworthy. We made use of sulfonimidamides in organo- [68] and metal catalysis [69,70], which, in part, required the development of new synthetic protocols [71,72,73,74,75]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Sulfonimidamide-Based Analog of Tasisulam and Its Biological Evaluation in the Melanoma Cell Lines SKMel23 and A375

Steinkamp¹,

Schmitt

Chen³

et al. 2016

Skin Pharmacol Physiol

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Tasisulam is a promising antitumor agent with complex pharmacology, which is used as an antiproliferative agent in patients with metastatic melanoma and other solid tumors. Phase 2 melanoma studies showed promising results but had to be stopped because of insufficient tasisulam clearance leading to toxic side effects. To reduce the negative effects of tasisulam, we synthesized a novel sulfonimidamide-based analog to evaluate its antiproliferative effects in comparison to the original compound by performing a cell proliferation assay in melanoma cell lines SKMel23 and A375. The results revealed that the analog had inhibitory effects on the proliferation comparable to tasisulam in both investigated cell lines. These results could contribute to a reduced toxicity of tasisulam and lead to further clinical trials in metastatic melanoma.

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“…In recent time, many improved and complementary oxidative and reductive methods have been reported in the literature to prepare SIAs from various starting materials such as sulfinylamine, sulfonimidoyl fluoride, sulfinamide, sulfonamide and sulfoximine . For a recent review see ref 34 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups

et al. 2019

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Herein, we report the synthesis of novel sulfonimidamides (SIAs) based on amino acid building blocks using a one‐pot method from tert‐butyldiphenylsilyl‐protected (TBDPS) sulfonamides, as well as exploration of orthogonal deprotection strategies. Among the several protecting groups investigated, TBDPS showed higher conversion, allowed UV detection and simple diastereomeric separation; in particular in combination with amino acid tert‐butyl esters. Moreover, we applied the present method to synthesize cyclic five‐membered acyl sulfonimidamides in two steps. The described synthesis of SIA‐based amino acid building blocks in combination with the orthogonal protection groups provide access to unnatural amino acid building blocks useful for further incorporation into larger molecules, such as peptide‐based transition‐state analogues and peptidomimetics. The chirality of the SIA group, as well as its additional point of diversity provided by the extra NH group, creates opportunities for the development of unique compound libraries that explore new chemical space, which is of considerable importance for the pharmaceutical and agrochemical industry.

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Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

Abstract: Background

Cited by 39 publications

References 23 publications

Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

Synthesis of a Sulfonimidamide-Based Analog of Tasisulam and Its Biological Evaluation in the Melanoma Cell Lines SKMel23 and A375

Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups

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Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

Abstract: Background

Cited by 39 publications

References 23 publications

Cu(OAc)2‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

Cu(OAc)2‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

Synthesis of a Sulfonimidamide-Based Analog of Tasisulam and Its Biological Evaluation in the Melanoma Cell Lines SKMel23 and A375

Synthesis of Sulfonimidamide‐Based Amino Acid Building Blocks with Orthogonal Protecting Groups

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Product

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Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides

Cu(OAc)₂‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides