91917-45-2

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 78758-74-4 C₁₂H₁₃NO 
• 91917-50-9 (4-methoxyphenyl)(1H-pyrrol-3-yl)methanone 
• 147089-55-2 2,4-Bis-[2-(4-methoxy-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrole 
• 147089-34-7 4-[2-(4-Methoxy-phenyl)-benzo[1,3]dithiol-2-yl]-2-[2-(4-methoxy-phenyl)-benzo[1,3]oxathiol-2-yl]-1H-pyrrole 
• 147089-44-9 (4-Methoxy-phenyl)-{4-[2-(4-methoxy-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrol-2-yl}-methanone 
• 147089-08-5 (4-Methoxy-phenyl)-{5-[2-(4-methoxy-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrol-3-yl}-methanone 
• 147088-91-3 2,4-bis(4-methoxybenzoyl)pyrrole 
• 147089-26-7 3-[2-(4-Methoxy-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrole 
• 147089-18-7 1-Benzenesulfonyl-3-[2-(4-methoxy-phenyl)-benzo[1,3]dithiol-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.

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.

PYRROLE CHEMISTRY XXV: A SIMPLIFIED SYNTHESIS OF SOME 3-SUBSTITUTED PYRROLES

A new synthesis is reported which allows the rapid preparation in good yield of 3-aroyl-, 3-acetyl- and 3-nitro- pyrroles from pyrrole utilizing the 1-benzenesulfonyl group as a blocking group.