62128-38-5

Usage

Uses

Used in Pharmaceutical Research and Development:
(4-Chlorophenyl)-(1H-pyrrol-3-yl)methanone is used as a research compound for the development of new pharmaceuticals, due to its potential as a building block for the synthesis of biologically active compounds.
Used in Agrochemical Research and Development:
(4-Chlorophenyl)-(1H-pyrrol-3-yl)methanone is used as a research compound for the development of new agrochemicals, due to its potential as a building block for the synthesis of biologically active compounds.
Used in Medicinal Chemistry:
(4-Chlorophenyl)-(1H-pyrrol-3-yl)methanone is used as a building block for the synthesis of various biologically active compounds in medicinal chemistry, due to its unique chemical structure and properties.

InChI:InChI=1/C11H8ClNO/c12-10-3-1-8(2-4-10)11(14)9-5-6-13-7-9/h1-7,13H

Upstream product

• 13169-71-6 2-(4-chlorobenzoyl)pyrrole 
• 97188-31-3 (1-benzenesulfonyl-1H-pyrrol-3-yl)-(4-chlorophenyl)methanone 
• 124-41-4 sodium methylate 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 147089-09-6 (4-Chloro-phenyl)-{5-[2-(4-chloro-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrol-3-yl}-methanone 
• 13169-71-6 2-(4-chlorobenzoyl)pyrrole 
• 147088-92-4 [4-(4-Chloro-benzoyl)-1H-pyrrol-2-yl]-(4-chloro-phenyl)-methanone 
• 156026-81-2 (E)-3-[3-(4-Chloro-benzoyl)-pyrrol-1-yl]-acrylic acid ethyl ester 
• 156026-85-6 (E)-3-{3-[(4-Chloro-phenyl)-hydroxy-methyl]-pyrrol-1-yl}-acrylic acid ethyl ester 
• 156026-89-0 (E)-3-{3-[(4-Chloro-phenyl)-imidazol-1-yl-methyl]-pyrrol-1-yl}-acrylic acid ethyl ester 
• 156026-97-0 3-[(4-Chloro-phenyl)-imidazol-1-yl-methyl]-1'H-[1,3']bipyrrolyl-4'-carboxylic acid 
• 156026-93-6 3-[(4-Chloro-phenyl)-imidazol-1-yl-methyl]-1'H-[1,3']bipyrrolyl-4'-carboxylic acid ethyl ester 
• 78758-76-6 3-(4-chlorobenzyl)-1H-pyrrole 
• 1314253-72-9 C₁₈H₁₅BrClN 

Relevant academic research and scientific papers

Antimalarial activity of natural and synthetic prodiginines

Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC50 = 1.7-8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC 50 > 2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right-hand terminal pyrrole, respectively. Potent in vitro activity (IC50 = 0.9-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogues were evaluated in a P. yoelii murine patent infection using oral administration. Each analogue reduced parasitemia by more than 90% after 25 (mg/kg)/day dosing and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 (mg/kg)/day, and 100% reduction at 25 (mg/kg)/day without any evident weight loses or clinical overt toxicity.

A study of the Friedel-Crafts acylation of 1-benzenesulfonyl-1H-pyrrole in the preparation of 3-aroylpyrroles

In this work, we studied the aluminum chloride catalyzed reaction of 1- benzenesulfonyl-1H-pyrrole with a series of eleven aroyl chlorides. The products formed were not isolated, but hydrolyzed to the target 3- aroylpyrroles in overall yields, usually, higher than 50%. However, in the CaSeS with the π electron rich 1-phenyl-1H-pyrrole-3-carbonyl chloride and 1-methyl-1H-indole-3-carbonyl chloride significant C-2 substitution occured, resulting in the isolation of the corresponding 1-benzenesulfonyl-2- aroylpyrroles as the predominant or the sole products. The desired C-3 isomers were synthesized starting with 1-triisopropylsilanyl-1H-pyrrole.

Antifungal agents. VIII. Synthesis and antifungal activities of bipyrryl analogues of bifonazole

Various bipyrryl analogues of bifonazole were synthesized starting from aryl-3-pyrryl-1-imidazolylmethanes. The introduction of a second pyrryl portion was performed by linking an acrylate moiety at 1-position of the pyrrole ring and then by treatment with TosMIC. The bipyrryl esters were hydrolyzed and decarboxylated to afford the required imidazoles. All new imidazole derivatives were tested against Candida albicans and Candida spp using as standard controls miconazole, bifonazole and ketoconazole.

General Methods for Synthesizing 2,4-Diacylpyrroles and their Precursors Containing One or Two Masked Acyl Groups

A thorough study of the synthesis of 2,4-diacylpyrroles by direct acylation of pyrrole and 2- and 3-acylpyrroles is reported.Among these, Friedel-Crafts acylation of 3-acylpyrroles is the most general and advantageous method because it utilises easily accessible starting materials.In addition it is always regiospecific and readily provides 2,4-diacylpyrroles containing identical or different acyl groups in very high yields (81-100percent) under mild conditions, Alternative procedures concern the synthesis of precursors of 2,4-diacylpyrroles containing one or two acyl groups masked by a 1,3-benzodithiolyl or 1,3-benzoxathiolyl group and subsequent hydrolysis with HgO-35percent aq.HBF4-Me2SO.Overall yields are always good (52-60percent).Indirect acylation constitutes a secure complement to direct acylation when it is necessary to operate in the presence of protected acyl groups.

Pyrrole chemistry. XXVIII. Substitution reactions of 1-(phenylsulfonyl)pyrrole and some derivatives

The preparative value of the 1-(phenylsulfonyl) N-blocking and directing group for the synthesis of 3-acylpyrroles has been further evaluated.Acetylation and benzoylation are strongly regiospecific and give good yields.However, the regiospecificity is not general and other substitution reactions give mixtures of 2- and 3-substitution or even mostly 2-substitution.Friedel and Crafts tert-butylation gives 3-tert-butyl-1-(phenylsulfonyl)pyrrole and provides a useful route to tert-butylpyrrole, but ethylation and isopropylation give mixtures.Acylations of 2- and 3-alkyl-1-(phenylsulfonyl)pyrroles show little evidence of useful regiospecificity.

Acid-Mediated Rearrangement of Acylpyrroles

N-Alkyl-2-acylpyrroles are converted by strong anhydrous acid to 1-alkyl-3-acylpyrroles.An equilibrium mixture of 2- and 3-acylpyrrole is produced by treatment of a 2- or 3-acyl NH pyrrole with acid.Pyrrolecarboxaldehydes similarly afford isomeric mixtures.A cross-ring migration, 7->8, is observed when the adjacent position is blocked.The mechanism of acid-mediated rearrangement of acylpyrroles is discussed.

Preparation of β-acyl pyrroles

A process for rearranging α-acyl pyrroles to β-acyl pyrroles which comprises reacting the former with an excess of a strong, anhydrous, non-oxidizing acid, preferably with heating.