Synthetic derivatives of spiro[pyrrolidinyl-3,3'-oxindole] alkaloids (coerulescine analogues) were investigated as new ligands for aminergic G-protein coupled receptors (GPCRs). The chemical starting point 2'-phenylspiro[indoline-3,3'-pyrrolidin]-2-one scaffold was identified by virtual fragment screening utilizing ligand- and structure based methods. As a part of the hit-to-lead optimization a...

The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the i...

In the title compound, C(21)H(20)N(4)O(4)S(2, )the piperazine ring adopts a chair conformation. The 1-ethyl-indoline-2,3-dione system links to one N atom of the piperazine ring via a carbodithio-ate group. The indoline-2,3-dione ring and the nitro-benzene ring subtend adihedral angle of 37.27 (7)°. In the crystal structure, weak C-H⋯O and π-π stacking inter-actions [centroid-centroid distances ...

The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2'-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2',3']pyrrolo[3',4':4,5]pyrrolo[2,1-a...

The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines c...

A novel donor-π-spacer-acceptor type organic dye (AK01) bearing a phenylenevinylene-conjugated system and a derivative of indoline donor was synthesized for dye-sensitized solar cells. AK01 showed panchromatic TiO(2) sensitization with high overall conversion efficiency of 6.2% under AM 1.5 illumination (100 mW cm(-2)).

Oxindoles and their indoline derivatives are common structural motifs found in a wide array of natural and biologically active molecules. Most catalytic methods for the asymmetric syntheses of these compounds rely heavily on the use of transition-metal catalysts. In contrast, alternative catalytic procedures involving organocatalysis are scarce. Herein we disclose a conceptually novel organocat...

The title mol-ecule, C(21)H(15)NO, has an indoline-2-one and two benzene substituent groups which are arranged in a propeller-like fashion around the central C atom. The dihedral angle between the two benzene rings is 73.32 (16)° and those between the benzene rings and the indoline-2-one group are 76.54 (14) and 67.69 (14)°. In the crystal, there is an inter-molecular N-H⋯O hydrogen-bonding int...

In the title compound, C(25)H(20)Cl(2)N(2)O(2), the pyrrolidine ring adopts an envelope conformation and the best plane through the five ring atoms makes a dihedral angle of 87.03 (8)° with the indoline ring. Mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into centrosymmetric dimers with an R(2) (2)(8) graph-set ring motif. C-H⋯O hydrogen bonds stabilize the crystal structure.

In the title compound, C(22)H(21)N(3)O(4), the central pyrrolidine ring adopts an envelope conformation with the N atom in the flap position. The indoline ring systems are almost perpendic-ular to the mean plane of the pyrrolidine ring, making dihedral angles of 86.4 (8) and 83.1 (8)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In thecrystal, N-H⋯O hydr...