97188-31-3

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 122-01-0 4-chloro-benzoyl chloride 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 123124-71-0 α,α-bis(4-chlorophenyl)-1-(phenylsulfonyl)pyrrole-3-methanol 
• 62128-38-5 (4-chlorophenyl)-(1H-pyrrol-3-yl)methanone 
• 62128-44-3 N-methyl-3-(4-chlorobenzoyl)-1H-pyrrole 
• 156026-72-1 (1-Benzenesulfonyl-1H-pyrrol-3-yl)-(4-chloro-phenyl)-methanol 
• 147089-19-8 1-Benzenesulfonyl-3-[2-(4-chloro-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrole 
• 1314253-72-9 C₁₈H₁₅BrClN 
• 1314253-29-6 C₁₃H₁₀ClNO₂ 
• 1314253-32-1 C₁₈H₂₀ClNO₂ 
• 1314253-42-3 C₁₈H₁₁ClFNO₂ 
• 1314253-43-4 C₁₈H₁₁BrClNO₂ 
• 78758-76-6 3-(4-chlorobenzyl)-1H-pyrrole 
• 123124-58-3 α,α-bis(4-chlorophenyl)-1H-pyrrole-3-methanol 
• 147089-56-3 2,4-Bis-[2-(4-chloro-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrole 
• 147089-35-8 4-[2-(4-Chloro-phenyl)-benzo[1,3]dithiol-2-yl]-2-[2-(4-chloro-phenyl)-benzo[1,3]oxathiol-2-yl]-1H-pyrrole 

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.

1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors

Various 1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-arylsulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. The compounds were identified as a novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HIV-1 activity.

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.

Estrogen Synthetase Inhibitors. 2. Comparison of the in Vitro Aromatase Inhibitory Activity for a Variety of Nitrogen Heterocycles Substituted with Diarylmethane or Diarylmethanol Groups

The preparation and in vitro aromatase inhibitory activity of a wide variety of heterocyclic (4,4'-dichlorodiphenyl)methanes and -methanols are described.The choice of the two diaryl-bearing moieties as a vehicle for the evaluation of the heterocycles was made by the comparison of series of imidazole and pyridine-derived compunds with similar pyrimidine compounds reported previously.A structural model for the most active compounds is also presented.The activity of a related series of compounds which contain two heterocyclic moieties was found to be consistent with the model.Many of the compounds evaluated, including representatives of the pyridine, imidazole, pyrimidine, pyrazole, triazole, thiazole, and isothiazole classes, exhibit EC50 potencies for aromatase inhibition at low nanomolar levels.These compunds are at least as potent as other nonsteroidal aromatase inhibitors reported previously.

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.