5825-63-8

Usage

Chemical Family

1-Methanesulfonylindoline belongs to the indoline family.

Molecular Weight

The molecular weight of 1-Methanesulfonylindoline is 195.24 g/mol.

Uses in Organic Synthesis

1-Methanesulfonylindoline is used as a versatile building block for the preparation of various biologically active molecules and pharmaceuticals.

Use in Agrochemicals and Dyes

1-Methanesulfonylindoline is utilized as an intermediate in the production of agrochemicals and dyes.

Therapeutic Properties

1-Methanesulfonylindoline exhibits potential therapeutic properties and has been studied for its anti-inflammatory and anti-cancer activities.

Unique Structure and Functional Groups

The unique structure and diverse functional groups of 1-Methanesulfonylindoline make it a valuable compound in organic and medicinal chemistry research.

Upstream product

• 496-15-1 1-indoline 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1374155-03-9 5-((4-methoxyphenyl)sulfonyl)-1-(methylsulfonyl)indoline 
• 1374155-04-0 5-((3,4-dimethoxyphenyl)sulfonyl)-1-(methylsulfonyl)indoline 

Relevant academic research and scientific papers

Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors

Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.

Oxidative palladium(II)-catalyzed C-7 alkenylation of indolines

A mild procedure for C-7-selective C-H alkenylation of various indolines under oxidative palladium(II) catalysis is reported. A fully substituted urea, formed by carbamoylation of the indoline nitrogen atom, functions as a directing group. Both α,β-unsaturated acceptors and styrenes participate in this direct C-H functionalization. With a free NH group at the urea terminus, the nitrogen atom subsequently cyclizes in a 1,4-fashion to yield a six-membered ring.

Sulfonamides for the Modulation of PKM2

The invention relates to sulfonamide compounds and methods for activating PKM2. The compounds and methods are useful in treating or preventing a disease or disorder selected from cancer, cell proliferative disorder, inflammatory disorder, metabolic disorder, and immune system disorder.

1-(sulfonyl)-5-(arylsulfonyl)indoline as activators of the tumor cell specific M2 isoform of pyruvate kinase

Cancer cells preferentially use glycolysis rather than oxidative phosphorylation for their rapid growth. They consume large amount of glucose to produce lactate even when oxygen is abundant, a phenomenon known as the Warburg effect. This metabolic change originates from a shift in the expression of alternative spliced isoforms of the glycolytic enzyme pyruvate kinase (PK), from PKM1 to PKM2. While PKM1 is constitutively active, PKM2 is switched from an inactive dimer form to an active tetramer form by small molecule activators. The prevalence of PKM2 in cancer cells relative to the prevalence of PKM1 in many normal cells, suggests a therapeutic strategy whereby activation of PKM2 may counter the abnormal cellular metabolism in cancer cells, and consequently decreased cellular proliferation. Herein we describe the discovery and optimization of a series of PKM2 activators derived from the 2-((2,3-dihydrobenzo[b][1,4] dioxin-6-yl)thio)-1-(2-methyl-1-(methylsulfonyl) indolin-5-yl) ethanone scaffold. The synthesis, SAR analysis, enzyme active site docking, enzymatic reaction kinetics, selectivity and pharmaceutical properties are discussed.

Structure-activity studies for a novel series of N-(arylethyl)-N- (1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines possessing dual 5- HT uptake inhibiting and α2-antagonistic activities

In search of an α2-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the α2-receptor (K(i) = 6.71 nM) and