Action of Nitrogen Trichloride on Proteins: Progress in the Isolation of the Toxic Factor

Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.; Moran, T. F.

doi:10.1038/163675a0

Cited by 70 publications

(59 citation statements)

References 6 publications

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“…Pale yellow oil. 1 Compound 2a (200 mg, 0.94 mmol) was dissolved in CH 2 Cl 2 (7 ml) and stirred at 08. A soln.…”

Section: Experimental Partmentioning

confidence: 99%

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Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Tye

Skinner

2002

HCA

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthdayThe synthesis of a range of 3-(phenylsulfonimidoyl)propanoate derivatives is described. A number of strategies for the imination of the key sulfoxide methyl 3-(penylsulfinyl)propanoate are discussed including the use of O-(mesitylsulfonyl)hydroxylamine (MSH) and iminoiodane reagents (PhÀINÀSO 2 R). A successful strategy for the preparation of the target compounds was the use of MSH followed by in situ coupling with a NBoc-protected amino acid. The pseudo-dipeptides thus formed exhibited interesting conformational properties in CDCl 3 solution giving evidence of intramolecular H-bonds in all cases, except for the proline derivative.

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“…Pale yellow oil. 1 Compound 2a (200 mg, 0.94 mmol) was dissolved in CH 2 Cl 2 (7 ml) and stirred at 08. A soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…Colourless oil. 1 Synthesis of 4,5-Dihydro-1-phenyl-3H-1l 6 -isothiazole-1,3-dione (5). Compound 2a (400 mg, 1.88 mmol) was dissolved in CH 2 Cl 2 (10 ml) and stirred at 08.…”

Section: Experimental Partmentioning

confidence: 99%

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Tye

Skinner

2002

HCA

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“…Their expanding application in drug design is exemplified in compound AZD6738 from AstraZeneca 8, 9. Moreover, since their discovery in the form of MSO,10 sulfoximines have been developed as ligands and auxiliaries for asymmetric synthesis11, 12 and directing groups in C−H functionalization,13, 14 as well as used in agrochemical agents such as sulfoxaflor 15…”

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confidence: 99%

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

et al. 2016

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A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts. Mixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines. This report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center. Control and mechanistic studies suggest a short‐lived electrophilic intermediate, which is likely to be PhINH or PhIN+.

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“…[6] Einige Jahre später wurde der toxische Faktor als das "Sulfoximin" von Methionin, Methioninsulfoximin (MSO, 2), identifiziert. [7] Die Verbindung konnte anschließend durch die Umsetzung von Stickstoffwasserstoffsäure mit Methioninsulfoxid (1) in Gegenwart konzentrierter Schwefelsäure synthetisch hergestellt werden (Schema 1). [8] Die Sulfoximingruppe war bis dahin unbekannt gewesen.…”

Section: Die Späte Entdeckung Der Sulfoximingruppeunclassified

Sulfoximine: Eine vernachlässigte Chance in der medizinischen Chemie

Lücking

2013

Angewandte Chemie

124

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Innovation ist häufig als der Schlüssel zur Wirkstoff‐Findung beschrieben worden. Doch in der täglichen Routine neigen Medizinalchemiker dazu, nur das Instrumentarium der funktionellen Gruppen und Strukturelemente zu verwenden, das sie bereits kennen und lieben. Das Blockbuster‐Krebsmedikament Velcade (Bortezomib) wurde beispielsweise von mehr als 50 Unternehmen abgelehnt, vermutlich wegen seiner ungewöhnlichen Boronsäuregruppe (“Only a moron would put boron in a drug!”). Auch im Entwicklungsprozess des pan‐CDK‐Inhibitors BAY 1000394 sorgte der unkonventionelle Vorschlag, eine Sulfoximingruppe in die Leitstruktur einzuführen, zunächst für Spott und Stirnrunzeln, da Sulfoximine selten in der medizinischen Chemie verwendet worden sind. Jedoch war es gerade die Sulfoximingruppe, die es schließlich ermöglichte, die fundamentalen Probleme des Projekts zu überwinden, und so zur Identifizierung des klinischen pan‐CDK‐Inhibitors BAY 1000394 führte. Der vorliegende Kurzaufsatz gibt einen Überblick über eine weithin vernachlässigte Chance in der medizinischen Chemie – die Sulfoximingruppe.

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Action of Nitrogen Trichloride on Proteins: Progress in the Isolation of the Toxic Factor

Cited by 70 publications

References 6 publications

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

Sulfoximine: Eine vernachlässigte Chance in der medizinischen Chemie

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