38168-18-2

Upstream product

• 91-56-5 indole-2,3-dione 
• 540-63-6 ethane-1,2-dithiol 

Downstream Products

• 59-48-3 2-oxoindole 
• 7511-08-2 3-benzyl-2-oxindole 
• 4717-90-2 3-(α-methylbenzylidene)oxidole 
• 3359-49-7 3-benzylideneoxindole 
• 15379-45-0 3-ethyloxindole 
• 1504-06-9 3-methylindolin-2-one 
• 108665-93-6 3-isopropyl-1,3-dihydroindol-2-one 

Relevant academic research and scientific papers

Novel 2-oxoindoline-based hydroxamic acids: Synthesis, cytotoxicity, and inhibition of histone deacetylation

In a continuation of a research program to discover novel small molecules targeting histone deacetylases, a series of 2′-oxospiro[1,3]dioxolane/dithiolane-2,3′-indoline-based hydroxamic acids have been designed and synthesized. These 2-oxoindoline-based hydroxamic acids displayed potent cytotoxicity against three human cancer cell lines, including SW620 (colon cancer), PC-3 (prostate cancer) and AsPC-1 (pancreatic cancer), with IC50 values as low as 0.05-0.07 μM, 74-fold lower than that of SAHA (1.64-3.70 μM). Additionally, compounds in this series exhibited good inhibition against histone-H3 and histone-H4 deacetylation, as evaluated by Western blot assay. These compounds also strongly inhibited HDAC2 with IC50 values as low as 0.03 μM. Docking studies performed using Autodock Vina showed all compounds bound to HDAC2 with relatively higher affinities (from -7.7 to -8.0 kcal/mol) compared to SAHA (-7.4 kcal/mol).

Synergistic Stereocontrol in the Enantioselective Ruthenium-Catalyzed Sulfoxidation of Spirodithiolane-Indolones

A chiral ruthenium catalyst was developed for the enantioselective sulfoxidation of the title compounds. The catalyst combines two elements of chirality, a chiral pybox ligand and a chiral bicylic lactam unit, to which the ligand is attached. The latter unit was shown to improve significantly the performance of the catalyst by exposing one of the two enantiotopic sulfur atoms to the active site via hydrogen-bond mediated coordination. Ten differently substituted substrates were converted into the respective sulfoxides in yields of 52-71% and with ≥90% ee. Hand-in-hand: Two spatially remote chiral entities act synergistically together in the Ru-catalyzed sulfoxidation reaction of the title compounds. Hydrogen bonds and π-π interactions are invoked to explain the preferential formation of a single stereoisomer in this reaction. High enantioselectivities (90-99% ee).