Synthesis of 5-[(Indol-2-on-3-yl)methyl]-2,2-dimethyl-1,3- dioxane-4,6-diones and Spirocyclopropyloxindole Derivatives. Potential Aldose Reductase Inhibitors

In the title indole derivatives, C 22 H 16 N 2 O 5 S, (I) and C 20 H 15 NO 3 S 2 , (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16) , respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O-S-O = 119.98 (9) and N-S-C = 104.01 (8) for compound (I) and O-S-O = 120.08 (18) and N-S-C = 104.91 (14) for compound (II)] and the sum of the bond angles at N indicates sp 2 hybridization. The molecules of both (I) and (II) feature intramolecular C-HÁ Á ÁO hydrogen bonds that generate S(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C-H-O hydrogen bonds, forming R 4 4 (18) ring motifs while molecules of (II) are linked by C-H-O and C-H-S hydrogen bonds, forming R 2 2 (12) ring motifs. Compound (II) was refined as an inversion twin.

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole

Dhanalakshmi¹,

Saravanan²,

Mohanakrishnan³

et al. 2017

“…For the biological activity of spiro-pyrrolidine and oxindole derivatives, see: Peddi et al (2004); Rajeswaran et al (1999). For a related crystal structure, see: .…”

Section: Related Literaturementioning

confidence: 99%

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Lai

Gallucci

2014

“…For applications of indole derivatives, see: Stevenson et al (2000); Ho et al (1986); Rajeswaran et al (1999). For comparison of molecular dimensions, see: Bassindale (1984); Sethu Sankar et al (2002); Allen (1981).…”

Section: Related Literaturementioning

confidence: 99%

Diethyl [(3-cyano-1-phenylsulfonyl-1H-indol-2-yl)methyl]phosphonate

Karthikeyan¹,

Sethusankar²,

Rajeshwaran

et al. 2011

In the title compound, C20H21N2O5PS, the indole ring is essentially planar, with a maximum deviation of −0.0083 (18) Å. The methyl C atom of the methylphosphonate group and the S atom lie 0.104 (2) and −0.2158 (6) Å, respectively, from the indole mean plane. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 82.30 (8)°. The ethyl side chains are disordered over two sets of sites, with occupancy factors of 0.737 (5)/0.263 (5) and 0.529 (11)/0.471 (11). In the crystal, molecules are linked into centrosymmetric dimers via C—H⋯O hydrogen bonds, resulting in an R 2 2(18) graph-set motif. The crystal structure is further stabilized by C—H⋯π interactions.