2-(3-Oxo-2,3-dihydro-1,2-benzothiazol-2-yl)acetic acid

Abstract

In the title compound, C9H7NO3S, the benzoisothia­zolone ring system is essentially planar, with a maximum deviation of 0.013 (2) Å. In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds, forming chains along [010]. In addition, weak inter­molecular C—H⋯O hydrogen bonds are present.

Crystal structure of methyl (S)-2-{(R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-1,2-thiazolidin-2-yl}-3-methylbutanoate: a chemical model for oxidized protein tyrosine phosphatase 1B (PTP1B)

“…In both molecules, the isothiozolidin-3-one ring adopts an envelope conformation with the methylene C atom (C1A in molecule A and C1B in molecule B) as the flap, similar to the conformation of oxidized PTP1B (pdb code: 1oem). In previously reported chemical models (1,2-benzisothiazole compounds) of PTP1B, the five-membered ring is planar (Kim et al, 1996;Ranganathan et al, 2002;Wang et al, 2011;Sivaramakrishnan et al, 2005). The S-N bond lengths in the title compound [S1A-N1A = 1.740 (2) Å and S1B-N1B = 1.733 (2) Å ], are similar to the same bond distance of ca 1.71 Å in oxidized PTP1B (pdb code: 1oem).…”

“…As part of early efforts in the area of cephalosporin synthesis, a dipeptide containing a protein sulfenyl amide residue was synthesized (Morin et al, 1973). However, to the best of our knowledge, there are no examples of low molecular weight sulfenyl amides that have been characterized crystallographically, although structures of related 1,2-benzisothiazol-3(2H)-ones have been reported (Kim et al, 1996;Ranganathan et al, 2002;Wang et al, 2011). Herein we describe the synthesis and crystal structure of the title compound, a low molecular weight mimic of oxidized PTP1B.…”

“…A search in the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014) for the substructure 1,2-benzisothiazole-3-one resulted in over twenty hits, which include three structures similar to the title compound: methyl 2-hydroxy-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoate (Ranganathan et al, 2002), 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid (Wang et al, 2011) and 2-phenethylbenzo[d]isothiazol-3(2H)one (Kim et al, 1996). In all three compounds, the fivemembered isothizolinone ring is planar.…”