Dariusz Witt

Recent Developments in the Synthesis of Unsymmetrical Disulfanes (Disulfides). A Review

The synthesis of unsymmetrical disulfanes is an important transformation in organic synthesis and medicinal chemistry. The current review is intended to summarize achievements in the synthesis of unsymmetrical disulfanes over the last decade (2004–2014).

DDQ-mediated synthesis of functionalized unsymmetrical disulfanes

We developed a simple and efficient method for the synthesis of functionalized unsymmetrical disulfanes under mild conditions in good yields. The designed method is based on the reaction of bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfane with thiols in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The developed method allows the preparation of unsymmetrical disulfanes bearing additional hydroxy, carboxy, or amino functionalities.

Synthesis and Biological Evaluation of Fluorinated 3-Phenylcoumarin-7-O-Sulfamate Derivatives as Steroid Sulfatase Inhibitors

In the present work, we report the initial results of our study on a series of 3‐phenylcoumarin sulfamate‐based compounds containing C‐F bonds as novel inhibitors of steroid sulfatase. The new compounds are potent steroid sulfatase inhibitors, possessing more than 10 times higher inhibitory potency than coumarin‐7‐O‐sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect on the enzymatic steroid sulfatase assay; both had IC50 values of 0.27 μm (the IC50 value of coumarin‐7‐O‐sulfamate is 3.5 μm, used as a reference).

Convenient and efficient synthesis of functionalized unsymmetrical alkynyl sulfides

We developed a simple and efficient method for the synthesis of functionalized unsymmetrical alkynyl sulfides under mild conditions in good yields. The designed method is based on the reaction of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-disulfanyl derivatives with lithium acetylides. The developed method allows the preparation of unsymmetrical alkynyl sulfides bearing additional hydroxyl, carboxyl, or amino functionalities.

The Organophosphorus Sulfenyl Bromides as Versatile Reagents for Cysteine Derivatives Functionalization by Unsymmetrical Disulfide Bond Formation

We have developed a convenient method for the synthesis of L-cysteine unsymmetrical disulfides under mild conditions with good to excellent yields. Described method is based on the straightforward preparation of the organophosphorus sulfenyl bromide readily available from bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl) disulfide. The unsymmetrical disulfides can be obtained for L-cysteine derivatives and thiols bearing neutral or acidic functionalities.

A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides

GRAPHICAL ABSTRACT ABSTRACT We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.