6140-11-0

Usage

Derived from

Acetophenone

Contains

Acetyl and amino groups

Substituent

Chlorine

Used in

Organic synthesis and pharmaceutical research

Purpose

Building block for bioactive compounds

Also used as

Intermediate in production of dyes and other organic compounds

Safety

Handle with caution and proper safety measures required.

Upstream product

• 551-93-9 2-aminoacetophenone 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 24186-98-9 4-methyl-quinoline-2,3-diol 
• 551-93-9 2-aminoacetophenone 
• 352353-29-8 2-(α-hydroxyethyl)(4-nitrophenoxy)acetanilide 
• 607-66-9 4-methyl-1,2-dihydroquinolin-2-one 
• 352353-15-2 4-[(2-acetyl-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester 
• 352353-13-0 N-(2-acetyl-phenyl)-2-(4-chloro-phenoxy)-acetamide 
• 352353-17-4 N-(2-acetyl-phenyl)-2-(2,6-dichloro-phenoxy)-acetamide 
• 352353-14-1 N-(2-acetyl-phenyl)-2-(4-nitro-phenoxy)-acetamide 

Relevant academic research and scientific papers

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF BOC-LINAGLIPTIN

This invention relates to novel processes for the synthesis of Linagliptin, the pharmaceutically active ingredient, and the key intermediate thereof, BOC-Linagliptin. (I) The processes are performed via new intermediate compounds of Formula (5) and Formula (3).

Linagliptin impurity as well as preparation method and application thereof

The invention belongs to the technical field of pharmaceutical chemistry, and specifically discloses a linagliptin impurity shown by formula I and a preparation method thereof, and also discloses application of the impurity as an impurity reference substa

Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization

PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.

Intramolecular Wittig reactions. A new synthesis of coumarins and 2-quinolones

o-Hydroxybenzaldehydes (1a-d) on reaction with chloroacetyl chloride in presence of pyridine followed by addition of triphenyl phosphine and base gave coumarins (2a-d). A similar sequence of reactions on o-aminoacetophenone/benzophenone (1e-f) and methyl anthranilate (1g) gave the corresponding 2-quinolones (2e-g).

A convenient method for the preparation of 3-phenoxy/thiophenoxy-2 (1H)-quinolinones

A number of new 4-methyl-3-phenoxy/thiophenoxy-2 (1H) quinolinones have been synthesized in excellent yields through a simple and efficient procedure from N-(2-acetylphenyl)-phenoxy/thiophenoxy acetamides under basic conditions.

New syntheses of 2-alkylthio-4-oxo-3,4-dihydroquinazolines, 2-alkylthioquinazolines, as well as their hetero analogues

N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-4-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with amines.