174574-69-7

Upstream product

• 1123-61-1 3,4-dichloro-1-methyl-pyrrole-2,5-dione 
• 959418-00-9 4-chloro-3-(1H-indol-3-yl)-1-phenyl-1H-pyrrole-2,5-dione 
• 74-89-5 methylamine 
• 120-72-9 indole 
• 1122-17-4 dichloromaleic acid anhydride 

Downstream Products

• 188884-38-0 3-(6-Benzyloxy-1H-indol-3-yl)-1-methyl-4-[1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 859832-23-8 1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole 
• 859832-27-2 1-(4-bromobenzenesulfonyl)-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole 
• 1359754-66-7 3-(1H-indol-3-yl)-4-(1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 
• 1359754-67-8 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 
• 1359754-68-9 3-(1H-indol-3-yl)-4-(1-(3-phenylmethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 
• 1359754-69-0 3-(1H-indol-3-yl)-4-(1-(2-phenoxyethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 
• 1359754-81-6 3-(1H-indol-3-yl)-4-(1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl)-maleimide 
• 1359754-82-7 3-(1H-indol-3-yl)-4-(1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl)-maleimide 
• 1359754-83-8 3-(1H-indol-3-yl)-4-(1-benzyl-1H-1,2,3-triazol-4-yl)-maleimide 
• 1359754-84-9 3-(1H-indol-3-yl)-4-(1-(2-phenoxyethyl)-1H-1,2,3-triazol-4-yl)-maleimide 

Relevant academic research and scientific papers

Indolylglycines Backbones in the Synthesis of Enantiopure 3,3-Spiroindolenines, Indolyl Tetracyclic Hemiaminals, and 3-Indolyl-maleimides Frameworks

This paper describes the synthesis of novel N-substituted 3-indolylglycines (3IGs), in high yields and optical purity via three-component Mannich reaction (3CR) of indole and free glyoxylic acid in the presence of primary and secondary aliphatic amines. By using this efficient approach, a series of racemic 3-indolylglycines (3IGs) as well as the optically pure (S)-3-indolylglycine ((S)-3IG) in multigram synthesis using (R-1-phenylethylamine ((R)-α-PEA) as chiral pool were synthetized. In parallel investigations, 3IGs were used as the starting material for the highly stereoselective synthesis of spiroindolenines bearing three controlled contiguous stereogenic centers. Despite our expectations, the N-chloroacetyl esters of 3IGs did not provide the expected spiroindolenine derivatives but led us to the discovery of a new methodology for the preparation of 3-indolylmaleimides (3IMs); compounds known for their broad range of important biological and fluorescence activities.

Synthesis and biological evaluation of 3-chloro-4-(indol-3-yl)-2,5- pyrroledione derivatives as antitumor agents

A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67～3.93 μM), would be a promising template for further development of novel antitumor agents.

Discovery and structural insight of a highly selective protein kinase inhibitor hit through click chemistry

Novel bisaryl maleimide derivatives to mimic natural kinase inhibitors were prepared through click chemistry. A highly selective hit was discovered in a 124-kinase-assay, and docking studies revealed a π-π stacking interaction with the Phe67 at the P-loop of GSK-3β kinase. The Royal Society of Chemistry 2012.

Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands

A series of N1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N 1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl) -1H-indole, 10a (Kb = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze.

Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines

Stable, water-soluble aminosugar staurosporine, K-252a and rebeccamycin analogs have been prepared by nucleophilic opening of C2-symmetric N-activated bis-aziridines by bis-indolylmaleimides. This divergent strategy allows the synthesis of unsymmetrical substituted derivatives and provides an easy access to the piperidine and pyrrolidine analogs.

Synthesis and cytotoxicity of indolopyrrolemaleimides

A series of indolopyrrolemaleimides have been synthesized and evaluated for their cytotoxicity in vitro against human leukemia cell line and four human solid cancer cell lines. Some of the compounds showed high or mediate activity against the lines. 6dc i

A general approach to the synthesis of bisindolylmaleimides: Synthesis of staurosporine aglycone

Bisindolylmaleimides are prepared in 65-95% yield by reaction of an indole Grignard with either 2,3-dichloro-N-methylmaleimide or 2,3-dichloromaleimide. A one-step synthesis of arcyriarubin A in 72% yield affords ready access to the staurosporine aglycone