313496-16-1

Basic information

• Product Name: indolin-1-yl(3,4,5-trimethoxyphenyl)methanone
• Synonyms: indolin-1-yl(3,4,5-trimethoxyphenyl)methanone;1-(3,4,5-trimethoxybenzoyl)indoline
• CAS NO: 313496-16-1
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.34776
• Mol File: 313496-16-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: indolin-1-yl(3,4,5-trimethoxyphenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: indolin-1-yl(3,4,5-trimethoxyphenyl)methanone(313496-16-1)
• EPA Substance Registry System: indolin-1-yl(3,4,5-trimethoxyphenyl)methanone(313496-16-1)

Safety Data

• Hazardous Substances Data: 313496-16-1(Hazardous Substances Data)

Upstream product

• 496-15-1 1-indoline 
• 39053-78-6 3,4,5-trimethoxyphenylacetyl chloride 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 

Downstream Products

• 917377-78-7 (S)-(+)-2-phenylindoline 
• 6597-31-5 N-(2,6-dimethylphenyl)-3,4,5-trimethoxybenzamide 

Relevant articles and documents

Discovery of indoline derivatives as anticancer agents via inhibition of tubulin polymerization

Human esophageal squamous cell carcinoma (ESCC) is one of the most lethal cancers in human digestive system. It is necessary to discover novel antitumor agents for the treatment of esophageal cancers because of its poor prognosis. Indoline has been reported as an efficient anticancer fragment to design novel anticancer agents. In this work, indoline derivatives were designed, synthesized and explored their anticancer activity. Compound 9d, which exhibited potent antiproliferative activity with IC50 values of 1.84 μM (MGC-803 cells), 6.82 μM (A549 cells), 1.61 μM (Kyse30 cells), 1.49 μM (Kyse450 cells), 2.08 μM (Kyse510 cells) and 2.24 μM (EC-109 cells), respectively. The most active compound 9d was identified as a tubulin inhibitor targeting colchicine binding site with an IC50 value of 3.4 μM. Compound 9d could strongly suppress the tubulin polymerization in Kyse450 cells. The results of molecular docking also suggested compound 9d could tightly bind into the colchicine binding site of tubulin. Besides, compound 9d inhibited the growth of KYSE450 cells in a time and dose-dependent manner. All the results suggest that the indoline derivatives may be a class of novel tubulin inhibitors with potential anticancer activity, and which is worthy of further study.

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Discovery of indoline derivatives that inhibit esophageal squamous cell carcinoma growth by Noxa mediated apoptosis

A series of novel indoline derivatives were synthesized and evaluated for antiproliferative activity against four selected cancer cell lines (Hela, A549, HepG2 and KYSE30). Among them, compound 20 displayed the potent inhibition activity against esophagea