861389-63-1

Upstream product

• 20780-76-1 5-iodoisatin 
• 5720-07-0 4-methoxyphenylboronic acid 
• 540-37-4 p-aminoiodobenzene 
• 1412900-32-3 5'-(4-methoxyphenyl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 106-40-1 4-bromo-aniline 
• 66475-83-0 N-(4-bromophenyl)-2-(hydroxyimino) acetamide 
• 34058-27-0 5′-iodospiro[[1,3]dioxolane-2,3′-indolin]-2′-one 
• 75822-54-7 5’-bromo-1‘,2’-dihydrospiro[1,3-dioxolane-2,3’-indole]-2’-one 
• 60313-92-0 p-iodoisonitrosoacetanilide 

Downstream Products

• 1412900-46-9 7-allyl-2-(4-methoxyphenyl)-7,8-dihydrodibenzo[e,g][1,4]diazocin-6(5H)-one 
• 1412900-39-0 3-allyl-3-((2-bromophenyl)amino)-5-(4-methoxyphenyl)indolin-2-one 

Relevant academic research and scientific papers

Synthesis and cytotoxic studies of novel 5-phenylisatin derivatives and their anti-migration and anti-angiogenic evaluation

A number of 5-arylisatin derivatives were synthesized in 5–6 steps from readily available starting materials. Their structures were confirmed by 1H NMR and 13C NMR as well as LC/MS. The cytotoxicity of these novel isatins against human leukemia K562 cells were evaluated by MTT assay in vitro. SAR studies indicated that the N-substituted benzyl and C-5 substituted phenyl groups greatly enhance their cytotoxic activity, whereas an intact carbonyl functionality on C-3 present in the parent ring is required to maintain such a potency. Particularly, N-(p-methoxybenzyl)-5-(p-methoxyphenyl)isatin (compound 2m) showed the highest antitumor activity against K562 cell lines (IC50 = 0.03 μM). Moreover, treatment with compound 2m significantly inhibited liver cancer HepG2 cells proliferation and migration, which could also reduce the human umbilical vein endothelial cells (HUVEC) tube formation. In conclusion, compound 2m exhibited very good cancer cells proliferation inhibition by angiogenesis responses in vitro, and 2m might be a promising angiogenesis inhibitor for cancer treatment.

Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3

Screening a library of small-molecule compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [3H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC50 values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacological characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a molecular modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes.

Novel synthesis and functionalization of ortho-ortho disubstituted biphenyls and a highly condensed novel heterocycle using radical cyclization reaction

This paper describes a novel synthetic route for the preparation of ortho-ortho disubstituted biphenyls and compounds possessing highly condensed ring system represented by structures X and Y, respectively. Several approaches, such as intermolecular Grubb's olefin metathesis, Heck and, Suzuki reactions were incorporated to functionalize the core structures of X and Y making it suitable for the preparation of a library of compounds.

Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction from iodoisatins

Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction with iodoisatins as key intermediates is described. A 'one pot' procedure is proposed.