99532-46-4

Usage

Uses

Used in Medicinal Chemistry:
1-[1-(benzenesulfonyl)-6-methoxy-indol-3-yl]ethanone is used as a building block or intermediate in the synthesis of pharmaceuticals for its unique reactivity and structural features, which can be leveraged to create novel drug candidates.
Used in Drug Development:
In the pharmaceutical industry, 1-[1-(benzenesulfonyl)-6-methoxy-indol-3-yl]ethanone is utilized as a key component in the development of new drugs, potentially targeting various therapeutic areas due to its versatile chemical properties and the possibility of forming diverse molecular interactions.

Upstream product

• 56995-13-2 6-methoxy-1-(phenylsulfonyl)-1H-indole 
• 108-24-7 acetic anhydride 
• 32431-44-0 2-(3-methoxyanilino)acetaldehyde diethyl acetal 
• 3189-13-7 6-methoxylindole 
• 1082892-90-7 3-(6-methoxy-1H-indol-3-yl)-3-oxopropanenitrile 
• 98-09-9 benzenesulfonyl chloride 
• 99532-52-2 1-(6-methoxy-1H-indol-3-yl)ethan-1-one 
• 99546-93-7 N-(2,2-diethoxyethyl)-N-(3-methoxyphenyl)-benzene-sulfonamide 

Downstream Products

• 1371572-77-8 C₁₇H₁₇NO₄S 
• 99532-52-2 1-(6-methoxy-1H-indol-3-yl)ethan-1-one 

Relevant academic research and scientific papers

Indole compound and applications thereof, and pharmaceutical composition and applications thereof

The present invention provides an indole compound and applications thereof, wherein the compound can effectively inhibit a CBP/EP300 Bromodomain receptor, and can be used as a drug for cancers, inflammatory diseases, autoimmune diseases, septicemia and viral infections.

An unusual and chemoselective reduction of ester grouping in nsubstituted-3-acetylindoles by sodium borohydride

Treatment of 3-acetylindoles 1(a-e) with ethyl chloroacetate in the presence of K2CO3 and tetrabutylammoniumbromide (TBAB) as phase transfer catalyst in DMF, resulted in the formation of the corresponding N-substituted derivatives, e

Novel and simple methodology for the synthesis of 3-acetylindoles and their N-alkyl derivatives using TBAB as phase transfer catalyst

Using 5% aq. NaOH, a simple method for the transformation of 3-cyanoacetylindoles 2(a-e) into 3-acetylindoles 3 (a-e), in good yields, is reported. Tetrabutylammoniumbromide (TBAB) is found to be an efficient phase transfer catalyst for the synthesis of N-alkyl derivatives 5(a-t) of 3-acetylindoles 3(a-e) giving products in excellent yields. 2 (a-e) were themselves obtained from simple indoles 1 (a-e) by reaction with cyano acetic acid in the presence of propionic anhydride at 100 °C for 5-10 min. Partial hydrolysis of 2 (a-e) under hot acidic conditions yielded the corresponding carboxamides α-(3-indolecarboxoyl)acetamides 4(a-e). Which could be readily transformed into the respective 3(a-e) by refluxing with 5% aq. NaOH for 2-2.5 h.

A Convenient Synthesis of 3-Acylindoles via Friedel-Crafts Acylation of 1-(Phenylsulfonyl)indole. A New Route to Pyridocarbazole-5,11-quinones and Ellipticine

A Friedel-Crafts acylation of 1-(phenylsulfonyl)indoles (1) with carboxylic acid anhydrides and acid chlorides in the presence of aluminum chloride gives 3-acyl-1-(phenylsulfonyl)indoles (2) in 81-99percent yields.Base hydrolysis converts 2 to 3-acylindoles (3) in 79-96percent yields.The reaction of 1-(phenylsulfonyl)indole (1a) with oxalyl chloride gives acid chloride 2h, which is converted to 3-cyanoindole (7) in three steps (75percent yield).Although a similar Friedel-Crafts alkylation of 1 was unsuccessful, in some cases the 3-acyl-1-(phenylsulfonyl)indoles 2a,e,f could be reduced to 3-alkyl-1-(phenylsulfonyl)indoles 8a,b,c in nearly quantitative yield with sodium borohydride in trifluoroacetic acid.The acid chloride derived from keto acid 9 did not cyclize to the desired pyridocarbazole-5,11-quinone 24 but rather to chloro keto lactam 10.However, acylation of 1a with acid chloride 22 followed by strong-base-mediated cyclization gives 24.Since quinone 24 has been previously converted to the alkaloid ellipticine 26, this route to 24 represents a new synthesis of ellipticine.Related synthetic schemes give rise to quinones 16 and 20.