23343-16-0Relevant articles and documents
Benzisothiazol-3-ones through a Metal-Free Intramolecular N–S Bond Formation
Yang, Ke,Zhang, Hao,Niu, Ben,Tang, Tiandi,Ge, Haibo
supporting information, p. 5520 - 5523 (2018/10/26)
The highly efficient synthesis of benzoisothiazol-3-ones from thiobenzamides has been described with good functional group compatibility and excellent yields. This work represents the first example of selectfluor-promoted N–S bond formation processes. This method provides a facile approach to access various important bioactive benzoisothiazol-3-ones.
Redox regulation of protein tyrosine phosphatase 1B (PTP1B): Importance of steric and electronic effects on the unusual cyclization of the sulfenic acid intermediate to a sulfenyl amide
Sarma, Bani Kanta
, p. 410 - 419 (2013/10/22)
The redox regulation of protein tyrosine phosphatase 1B (PTP1B) via the unusual transformation of its sulfenic acid (PTP1B-SOH) to a cyclic sulfenyl amide intermediate is studied by using small molecule chemical models. These studies suggest that the sulfenic acids derived from the H2O 2-mediated reactions o-amido thiophenols do not efficiently cyclize to sulfenyl amides and the sulfenic acids produced in situ can be trapped by using methyl iodide. Theoretical calculations suggest that the most stable conformer of such sulfenic acids are stabilized by n O→σ* S-OH orbital interactions, which force the -OH group to adopt a position trans to the S· · ·O interaction, leading to an almost linear arrangement of the O· · ·S-O moiety and this may be the reason for the slow cyclization of such sulfenic acids to their corresponding sulfenyl amides. On the other hand, additional substituents at the 6-position of o-amido phenylsulfenic acids that can induce steric environment and alter the electronic properties around the sulfenic acid moiety by S· · ·N or S· · ·O nonbonded interactions destabilize the sulfenic acids by inducing strain in the molecule. This may lead to efficient the cyclization of such sulfenic acids. This model study suggests that the amino acid residues in the close proximity of the sulfenic acid moiety in PTP1B may play an important role in the cyclization of PTP1B-SOH to produce the corresponding sulfenyl amide.
Reactions of N-sulfenyl-1,2-benzisothiazolin-3-ones with nucleophiles
Bao, Ming,Shimizu, Masao,Shimada, Shigeru,Inoue, Jun'ichi,Konakahara, Takeo
, p. 11359 - 11366 (2007/10/03)
Reactions of N-[2-(alkoxycarbonyl)benzenesulfenyl]-1,2-benzisothiazolin-3- ones (1) with various nucleophiles were examined. Anions of active methylene compounds attacked the sulfur atoms of the sulfenyl moieties of 1 to afford sulfide compounds, while th
