193354-13-1

Basic information

• Product Name: 2H-INDOL-2-ONE, 1,3-DIHYDRO-5-IODO-
• Synonyms: 2H-INDOL-2-ONE, 1,3-DIHYDRO-5-IODO-;5-IODO-1,3-DIHYDRO-INDOL-2-ONE;5-iodoindolin-2-one
• CAS NO: 193354-13-1
• Molecular Formula: C₈H₆INO
• Molecular Weight: 259.04381
• Mol File: 193354-13-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2H-INDOL-2-ONE, 1,3-DIHYDRO-5-IODO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-INDOL-2-ONE, 1,3-DIHYDRO-5-IODO-(193354-13-1)
• EPA Substance Registry System: 2H-INDOL-2-ONE, 1,3-DIHYDRO-5-IODO-(193354-13-1)

Safety Data

• Hazardous Substances Data: 193354-13-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2H-Indol-2-One, 1,3-DiHydro-5-Iodois used as a key intermediate in drug synthesis for its unique properties. The presence of the Iodo group at the 5th position allows for various chemical reactions that can be harnessed in the development of new pharmaceutical compounds. This makes it a valuable asset in the creation of novel drugs and therapeutic agents.
Used in Chemical Reactions:
2H-Indol-2-One, 1,3-DiHydro-5-Iodois used as a reactant in various chemical reactions due to the reactivity of the Iodo group. This property enables the compound to participate in a range of chemical processes, making it a versatile building block for the synthesis of other complex molecules and compounds. Its application in chemical reactions can lead to the development of new materials and products across different industries.

Upstream product

• 59-48-3 2-oxoindole 
• 16066-91-4 5-iodo-1H-indole 
• 20780-76-1 5-iodoisatin 

Downstream Products

• 220904-83-6 3-(3,5-dibromo-4-hydroxy-benzylidene)-5-iodo-1,3-dihydro-indol-2-one 
• 199328-10-4 methyl 2-oxoindoline-5-carboxylate 
• 220904-98-3 5-pyridin-3-yl-1,3-dihydro-2H-indol-2-one 
• 1279104-65-2 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzoic acid methyl ester 
• 1279104-66-3 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide 
• 1279104-67-4 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzamide 
• 1279104-68-5 4-[2-(2-Chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzonitrile 
• 1279107-83-3 Ethyl 2-(2-chlorophenyl)-5-(4-(methoxycarbonyl)-2-methylphenyl)-1H-indole-1-carboxylate 
• 1279106-98-7 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzoic acid 
• 139487-11-9 5-iodo-1,3,3-trimethylindolin-2-one 
• 1225538-09-9 5-(4-fluorophenyl)indolin-2-one 

Relevant articles and documents

Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives

In the course of structure-activity relationship studies, diversely substituted 1-(β- d-acetylatedglucopyranosyl)isoindigo derivatives were prepared from indolines. New 7′-azaisoindigo analogues were also synthesized by coupling a glycosylated isatine and a 7-azaindolin-2-one derivative. Compounds containing a 7′-azaisoindigo framework have never been described before. To get an insight into the substitution pattern required for the best biological potencies, their antiproliferative activities were evaluated toward a human buccal carcinoma cell line (KB) and two human myeloid leukaemia cell lines (K562, HL60).

Radioiodinated sunitinib as a potential radiotracer for imaging angiogenesis - Radiosynthesis and first radiopharmacological evaluation of 5-[125I]Iodo-sunitinib

Sunitinib (SU11248) is a highly potent tyrosine kinase inhibitor targeting vascular endothelial growth factor receptor (VEGFR). Radiolabeled inhibitors of RTKs might be useful tools for monitoring RTKs levels in tumour tissue giving valuable information for anti-angiogenic therapy. We report here the synthesis of a 125I-labeled derivative of sunitinib and its first radiopharmaceutical characterization. The non-radioactive reference compound 5-iodo-sunitinib 4 was prepared by Knoevenagel condensation of 5-iodo-oxindole with the corresponding substituted 5-formyl-1H-pyrrole. In a competition binding assay against VEGFR-2 a binding constant (Kd) of 16 nM for 4 was found. The ability of 4 to inhibit tyrosine kinase activity was demonstrated on RTK expressing cells suggesting this radiotracer as a useful tool for monitoring VEGFR expression. 5-[125I]lodo-sunitinib, [ 125I]-4 was obtained via destannylation of the corresponding tributylstannyl precursor with [125I]NaI in the presence of H 2O2 in high radiochemical yield (>95%) and radiochemical purity (a low non-specific binding of 5-10%. Preliminary biodistribution studies of [ 125I]-4 in healthy CD-1 mice showed a relatively high uptake in VEGFR-2 rich tissues like kidney and lung followed by rapid washout (9.6 and 9.7; 4.5 and 3.8% ID/g of kidney and lung at 1 and 4 h, respectively).

Compounds for preventing or treating lipid metabolism-related diseases

The present invention relates to the field of biomedicines, and in particular to a structure capable of binding LC3 and a structure capable of binding a lipid droplet linked together by a covalent linkage, thereby forming a 'LC3 binding moiety - lipid dro

Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids

Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.

Synthesis, Biological, and Computational Evaluation of Novel 1,3,5-Substituted Indolin-2-one Derivatives as Inhibitors of Src Tyrosine Kinase

Several substituted indolin-2-one derivatives were synthesized and evaluated for their activities against Src kinase. Several compounds showed activity against Src, with IC50 values in the low micromolar range. Among them, compound 2f showed the most significant activity with an IC50 value of 1.02 μM. Molecular docking studies have been performed for evaluation of the binding modes of compound 2f into the Src active site. The docking structure of compound 2f disclosed that the indole NH forms a hydrogen bond with the carbonyl of Met341. These results suggest that our novel compound 2f is a promising compound for the further development of indole-based drugs targeting Src kinase. A novel series of indole-2-one derivatives were synthesized and evaluated for their Src inhibitory activities. Compound 2f was found as the most promising compound with an IC50 value of 1.02 μM. Molecular docking studies were performed to disclose the binding mode for compound 2f.

General synthesis of mono-, di-, and tri-acetylated indoles from indolin-2-ones

Having developed the one-pot triacetylation of indolin-3-ones, we have now devised a simple two-step reaction sequences to produce di- and mono-acetylated indoles from indolin-2-ones. The indolin-2-ones were first subjected to acetylation in the presence of acetic anhydride and a catalytic amount of N,N-dimethylaminopyridine to give 2-acetoxy-1,3-diacetylindoles. Subsequently, an enzyme-assisted deacetylation resulted in the chemoselective deprotection of the acetoxy group to produce 1,3-diacetyl-2-hydroxyindoles. However, a chemical deacetylation of 2-acetoxy-1,3-diacetylinoles under mild basic or acidic conditions resulted in the formation of 3-acetyl-2-hydroxyindoles.

INDOLE DERIVATIVES AS CRAC MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein R1, R2, R3 and R4 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with calcium release-activated calcium channels (CRAC).

Pyrrole substituted 2-indolinone protein kinase inhibitors

The present invention relates to novel pyrrole substituted 2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.