147089-03-0

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 142-61-0 Hexanoyl chloride 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 147089-22-3 1-Benzenesulfonyl-3-(2-pentyl-benzo[1,3]dithiol-2-yl)-1H-pyrrole 
• 147089-14-3 1-[5-(2-Cyclohexyl-benzo[1,3]dithiol-2-yl)-1H-pyrrol-3-yl]-hexan-1-one 
• 147088-98-0 1-(5-Cyclohexanecarbonyl-1H-pyrrol-3-yl)-hexan-1-one 
• 148735-49-3 1-(5-Benzoyl-1H-pyrrol-3-yl)-hexan-1-one 
• 62217-28-1 2-cyclohexylidene-1,3-benzodithiole 

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.

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.