The synthesis of boron-pyridyl-imino-isoindoline dyes, a novel type of BODIPY analogue, involves a facile and scalable two-step reaction. Broad envelopes of intense vibrational bands are observed for the main spectral bands in the absorption and emission spectra. High fluorescence quantum yields are obtained in solution, with significant intensity also observed in the solid-state.

In the title compound, C(15)H(10)N(2)O(3), the isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds are observed.

Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.

An isoindoline-nitroxide derivative of guanine (Ǵ, "G-spin") was shown to bind specifically and effectively to abasic sites in duplex RNAs. Distance measurements on a Ǵ-labeled duplex RNA with PELDOR (DEER) showed a strong orientation dependence. Thus, Ǵ is a readily synthesized, orientation-selective spin label for "mix and measure" PELDOR experiments.

The title compound, C(15)H(9)ClN(2)O(2), adopts an E configuration about the C=N double bond. The mean plane of the isoindoline ring system [maximum deviation = 0.011 (2) Å] is inclined to the chloro-benzene ring by 22.62 (8)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming chains that propagate along [010].

Focused structure-activity relationships of isoindoline class DPP-IV inhibitors have led to the discovery of 4b as a highly selective, potent inhibitor of DPP-IV. In vivo studies in Wistar/ST rats showed that 4b was converted into the strongly active metabolite 4l in high yield, resulting in good in vivo efficacy for antihyperglycemic activity.

In the title compound, [Ca(C(32)H(24)N(3)O(2)P(2))(2)], the 1,3-bis-(diphenyl-phosphinoylimino)isoindoline ligand adopts a tridentate coordination mode. The compound exhibits a distorted octa-hedral geometry. The Ca atom lies on a twofold rotation axis.

Nucleosides spin-labelled with isoindoline-derived benzimidazole ((Im)U) and benzoxazole ((Ox)U) moieties were synthesized and incorporated into DNA oligonucleotides. Both labels display limited mobility in duplex DNA but (Im)U was less mobile, which was attributed to an intramolecular hydrogen bond between the N-H of the imidazole and O4 of the uracil nucleobase.