197460-26-7

Basic information

• Product Name: 1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester, (2S)-
• Synonyms: 1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester, (2S)-;(S)-tert-butyl 2-((tosyloxy)methyl)indoline-1-carboxylate;tert-Butyl (S)-2-((tosyloxy)methyl)indoline-1-carboxylate
• CAS NO: 197460-26-7
• Molecular Formula: C₂₁H₂₅NO₅S
• Molecular Weight: 403.4919
• Mol File: 197460-26-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester, (2S)-(197460-26-7)
• EPA Substance Registry System: 1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester, (2S)-(197460-26-7)

Safety Data

• Hazardous Substances Data: 197460-26-7(Hazardous Substances Data)

Usage

Molecular weight

393.46 g/mol

Structure

1H-Indole-1-carboxylic acid, 2,3-dihydro-2-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-, 1,1-diMethylethyl ester

Solubility

The compound is likely to be poorly soluble in water due to its complex structure and the presence of hydrophobic groups.

Stability

The compound is stable under normal conditions, but may degrade upon exposure to heat, light, or other forms of stress.

Biological activity

The compound has potential anti-inflammatory, anti-cancer, and anti-viral properties and is commonly used as a reference compound for the biological activities of indirubin derivatives.

Stereochemistry

The compound has a chiral center and exists as a single stereoisomer with the (2S)-configuration.

Derivatives

The compound is an ester derivative of the naturally occurring indole compound indirubin.

Medicinal chemistry

The compound is of interest in medicinal chemistry for the development of new pharmaceuticals.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 197460-25-6 (S)-tert-butyl 2-(hydroxymethyl)indoline-1-carboxylate 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 27640-33-1 (2S)-2,3-dihydro-1H-indole-2-ylmethanol 
• 79815-20-6 (S)-indoline-2-carboxylic acid 

Downstream Products

• 517866-45-4 1-(chloroacetyl)-2-methylindoline 
• 1373444-98-4 C₄₀H₄₉ClN₂O₅S 
• 869224-31-7 (S)-2-Phenoxymethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Design and synthesis of novel indoline-(thio)urea hybrids

A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.

MORPHOLINO COMPOUNDS, USES AND METHODS

The invention relates to morpholino-derivatives according to Formula (I) or stereoisomers or pharmaceutically acceptable salts or solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7/s

5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)-A potent FLAP inhibitor

A series of potent 5-lipoxygenase-activating protein (FLAP) inhibitors are herein described. SAR studies focused on the discovery of novel alicyclic moieties appended to an indole core to optimize potency, physical properties and off-target activities. Subsequent SAR on the N-benzyl substituent of the indole led to the discovery of compound 39 (AM679) which showed potent inhibition of leukotrienes in human blood and in a rodent bronchoalvelolar lavage (BAL) challenge model.