Thiazolidinedione: A Privileged Scaffold for the Development of Anticancer Agents.

Thiazolidinedione, an important heterocyclic ring system, is a pharmacophore and a privileged scaffold in medicinal chemistry. Researchers have shown its potential application as a backbone for inhibitors, as it is involved in anticancer development strategies, cancer progression and metastasis. In this paper, the anticancer activities of thiazolidinedione derivatives were reviewed for the first time with respect to different substituents and their positions. This work may imitate a stirring wheel to guide further advanced development of new anticancer molecules with high efficacy.

2,3-Dibromo-6-meth-oxy-4-[(phenethyl-amino)-methyl-idene]cyclo-hexa-2,5-dien-1-one methanol monosolvate.

In the title compound, C(16)H(15)Br(2)NO(2)·CH(4)O, the mean planes of the substituted cyclo-hexa-2,5-dien-1-one and phenyl rings are almost parallel [dihedral angle = 7.84 (4)°]. The crystal packing is stabilized by N-H⋯O hydrogen bonds generating infinite [101] chains. The methanol solvent mol-ecules are connected with the main species by O-H⋯O inter-actions.

(E)-4-Chloro-N-[4-(methyl-sulfon-yl)benzyl-idene]aniline.

In the crystal structure of the title compound, C(14)H(12)ClNO(2)S, the mol-ecules display a trans conformation with respect to the C=N double bond. The dihedral angle between the methyl-sulfonyl benzene and chloro-benzene rings is 59.59 (8)°. The crystal packing is stabilized by weak C-H⋯O inter-actions and by π-π stacking inter-actions between inversion-related methyl-sulfonyl benzene rings [centroid-centroid distance = 3.8579 (11) Å].

N-[(E)-4-(Methyl-sulfon-yl)benzyl-idene]-3-nitro-aniline.

In the title compound, C(14)H(12)N(2)O(4)S, the dihedral angle between the two aromatic rings is 35.65 (12)°. The crystal packing is stabilized by weak C-H⋯O hydrogen bonds and aromatic π-π ring stacking inter-actions [minimum ring centroid separation = 3.697 (3) Å].

rac-Ethyl 2-amino-3-hy-droxy-3-[4-(methyl-sulfon-yl)phen-yl]propano-ate.

In the title compound, C(12)H(17)NO(5)S, the orientations of the 2-ethyl-2-amino-3-hy-droxy-propano-ate group and the 4-methyl-sulfonyl moiety towards the aromatic ring are periplanar and (-)-anti-clinal, respectively. In the crystal packing, the dominant inter-action is O-H⋯N hydrogen bonding, which generates a chain running along [100]. N-H⋯O and C-H⋯O interactions are also observed.

2-Aza-niumyl-4-(ethyl-carbamo-yl)butano-ate: the zwitterionic form of the amino acid theanine.

In the title zwitterion, C(7)H(14)N(2)O(3), the ethyl-amino and the 5-oxo groups are positionally disordered with occupancy ratios of 0.50:0.50 and 0.70:0.30, respectively. The terminal ethyl -CH(3) group undergoes considerable thermal motion. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming a two-dimensional arrangement propagating in the bc plane.