31107-06-9

Usage

General Description

1H-indole-2,3-dione 3-[(4-nitrophenyl)hydrazone] is a chemical compound with the molecular formula C14H9N5O4. It is a bright yellow solid that is commonly used in organic synthesis and as a reagent in chemical reactions. The compound is a hydrazone derivative of 1H-indole-2,3-dione and has nitrophenyl substituents, making it useful in the synthesis of various organic compounds. It has been investigated for its potential applications in medicinal chemistry and as a building block in the development of new pharmaceuticals. The compound is also of interest for its potential biological and pharmacological properties, although further research is needed to fully understand its potential uses.

InChI:InChI=1/C14H10N4O3/c19-14-13(11-3-1-2-4-12(11)15-14)17-16-9-5-7-10(8-6-9)18(20)21/h1-8,16H,(H,15,17,19)

Upstream product

• 91-56-5 indole-2,3-dione 
• 100-16-3 4-nitrophenylhydrazone 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 

Relevant academic research and scientific papers

Isatin-phenylhydrazone dyes and boron complexes with large Stokes shifts: Synthesis and solid-state fluorescence characteristics

Isatin-phenylhydrazone derivatives and their corresponding BF2-complexes were efficiently synthesized by a three-step reaction starting from isatin and phenylhydrazine hydrochloride. The optical properties of these isatin-phenylhydrazone derivatives and their difloroboron complexes were investigated in different organic solvents and in the solid-state. Although these fluorescent dyes exhibit feeble fluorescent intensity in solution-state, high fluorescent intensity can be detected in their solid-state. The Stokes shift of these dyes can be achieved 95-198 nm versus the typical BF2-complexes (ca. 15 nm) in the solid-state, which were caused by the remarkable geometry relaxation upon photoexcitation and its substantial effect on the energy levels of molecular orbitals. Information supporting this inference was supported by the density functional theory calculations.

Synthesis, biological activity and docking study of some new isatin Schiff base derivatives

A set of novel Schiff bases of isatin were synthesized and characterized by reaction of isatin with various aromatic or heterocyclic primary amines. Cytotoxic activities for some of the synthesized compounds were evaluated byMTTassay in three human cancer cell lines (HeLa, LS180 and Raji). Half of the tested compounds showed good cytotoxicity in HeLa cells. 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one was found to be the most potent molecule among the studied isatin derivatives. Docking studies of 3-substituted indolin-2-one scaffolds on vascular endothelial growth factor receptor 2 (VEGFR-2) involved in cell proliferation and angiogenesis was performed. 3-(naphthalen-1-ylimino) indolin-2-one and 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one exhibited higher docking binding energies with receptor. For 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one, H-bond interaction with Cys917 residue of target active site was in common with reported crystallographic benzoimidazole derivative (PDB code: 2OH4). New key H-bonds involving Glu915, Asn921, and Arg1049 residues in VEGFR-2 active site could be detected for 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one. Extended lipophilic rings containing H-bond acceptors on the 3 position of indoline scaffold seemed to be important factors in developing potent VEGFR-2 inhibitors virtually. Based on the ligand efficiency indices, some isoxazole or thiazole substituted isatin derivatives may be regarded as efficient candidates for further molecular developments of anticancer agents. Springer Science+Business Media, LLC 2011.