52266-24-7

Usage

Chemical structure

A pyrrole derivative with two methyl groups and a phenyl group attached to the nitrogen atom

Physical state

Dark brown liquid at room temperature

Uses

a. Precursor in the synthesis of various pharmaceuticals and organic compounds
b. Exhibits biological activities

Biological activities

a. Antimicrobial properties
b. Antioxidant properties

Potential applications

a. Materials science
b. Development of organic semiconductors
c. Development of dyes

Upstream product

• 64-19-7 acetic acid 
• 1192717-69-3 1,5-dimethyl-3-phenyl-1H-pyrrole-2,4-dicarboxylic acid 
• 60317-41-1 ethyl 2-(hydroxyimino)-3-oxo-3-phenylpropanoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1817-57-8 4-phenyl-3-butyne-2-one 

Downstream Products

• 1192719-19-9 (1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)-oxo-acetyl chloride 
• 1357024-62-4 methyl 3-(4-dodecanoyl-1,5-dimethyl-3-phenylpyrrol-2-yl)propionate 
• 1357024-25-9 3-(4-dodecanoyl-1,5-dimethyl-3-phenylpyrrol-2-yl)propionic acid 
• 161561-00-8 methyl 3-(1,5-dimethyl-3-phenylpyrrol-2-yl)propionate 
• 1192720-23-2 2-(1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)-N-{4-[4-(4,6-dimethylpyridin-2-yl)piperazin-1-yl]phenyl}-2-oxoacetamide 

Relevant academic research and scientific papers

METHOD OF TREATING COCCIDIOIDES INFECTION

The invention relates to the therapeutic use of olorofim, 2-(1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide in the prevention and treatment of a fungal infection caused by a Coccidioides species.

PHARMACEUTICAL FORMULATION

A pharmaceutical composition suitable for oral administration comprising particles of 2-(1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide is provided. Also provided is a pharmaceutical composition suitable for parenteral administration wherein the composition comprises 2-(1,5-dimethyl- 3-phenyl-1H-pyrrol-2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide. The compositions are useful in the treatment of fungal infection in a subject in need thereof.

ANTIFUNGAL AGENTS

The invention provides a pyrrole compound, which compound is (a)2-(1,5-dimethyl-3- phenyl-1H-pyrrol-2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2- oxoacetamideor a deuterated derivative thereof, or(b)2-(1,5-dimethyl-3-phenyl-1H-pyrrol- 2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)-3-hydroxyphenyl)-2-oxoacetamide or a deuterated derivative thereof, or (c) a prodrug of compound (a) or a prodrug of compound (b), or a pharmaceutically acceptable salt or agriculturally acceptable salt of (a), (b) or (c). Also provided are combinations and compositions comprising the compound and known antifungal agents. The invention also relates to the therapeutic use of a compound of the invention in prevention or treatment of fungal diseases. It also relates to the use of:2-(1,5-dimethyl-3-phenyl-1H- pyrrol-2-yl)-N-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide or an agriculturally acceptable salt thereof, or 2-(1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)-N-(4-(4- (5-fluoropyrimidin-2-yl)piperazin-1-yl)-3-hydroxyphenyl)-2-oxoacetamide or an agriculturally acceptable salt thereof, as an agricultural fungicide.

PYRROLE ANTIFUNGAL AGENTS

The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.

A facile synthesis of polysubstituted pyrroles

(equation presented) α-Aminoalkylcuprates prepared from CuX·2LiCI (X = Cl, CN) and 1 equiv of an α-lithiocarbamate undergo conjugate addition reactions to α,β-alkynyl ketones in moderate to good yields, affording E:Z mixtures of α,β-enones. Treatment of the conjugate adducts with PhOH/TMSCI in CH2CI2 effected carbamate deprotection and cyclization to afford a flexible two-step synthesis of substituted pyrroles.