17823-87-9

Usage

InChI:InChI=1/C15H17NO/c16-14-9-4-10-15(12-14)17-11-5-8-13-6-2-1-3-7-13/h1-4,6-7,9-10,12H,5,8,11,16H2

Upstream product

• 17399-20-1 3-(3-phenylpropoxy)nitrobenzene 
• 554-84-7 meta-nitrophenol 
• 909356-79-2 N-(3-(3-phenylpropoxy)phenyl)acetamide 
• 621-42-1 meta-hydroxyacetanilide 
• 637-59-2 1-Bromo-3-phenylpropane 

Downstream Products

• 71218-98-9 N-[3-(3-Phenyl-propoxy)-phenyl]-propionamide 
• 71219-01-7 [3-(3-Phenyl-propoxy)-phenyl]-carbamic acid methyl ester 
• 71218-99-0 N-[3-(3-Phenyl-propoxy)-phenyl]-isobutyramide 
• 71219-00-6 Cyclopropanecarboxylic acid [3-(3-phenyl-propoxy)-phenyl]-amide 
• 71219-07-3 [3-(3-Phenyl-propoxy)-phenyl]-carbamic acid 2,2,2-trifluoro-ethyl ester 

Relevant academic research and scientific papers

Quinolone-based compounds, formulations, and uses thereof

Provided herein are quinolone-based compounds that can be used for treatment and/or prevention of malaria and formulations thereof. Also provided herein are methods of treating and/or preventing malaria in a subject by administering a quinolone-based compound or formulation thereof provided herein.

ICI 56,780 optimization: Structure-activity relationship studies of 7-(2-phenoxyethoxy)-4(1H)-quinolones with antimalarial activity

Though malaria mortality rates are down 48% globally since 2000, reported occurrences of resistance against current therapeutics threaten to reverse that progress. Recently, antimalarials that were once considered unsuitable therapeutic agents have been revisited to improve physicochemical properties and efficacy required for selection as a drug candidate. One such compound is 4(1H)-quinolone ICI 56,780, which is known to be a causal prophylactic that also displays blood schizonticidal activity against P. berghei. Rapid induction of parasite resistance, however, stalled its further development. We have completed a full structure-activity relationship study on 4(1H)-quinolones, focusing on the reduction of cross-resistance with atovaquone for activity against the clinical isolates W2 and TM90-C2B, as well as the improvement of microsomal stability. These studies revealed several frontrunner compounds with superb in vivo antimalarial activity. The best compounds were found to be curative with all mice surviving a Plasmodium berghei infection after 30 days.

Design, synthesis, and anti-HCV activity of thiourea compounds

A series of thiourea derivatives were synthesized and their antiviral activity was evaluated in a cell-based HCV subgenomic replicon assay. SAR studies revealed that the chain length and the position of the alkyl linker largely influenced the in vitro anti-HCV activity of this class of potent antiviral agents. Among this series of compounds synthesized, the thiourea derivative with a six-carbon alkyl linker at the meta-position of the central phenyl ring (10) was identified as the most potent anti-HCV inhibitor (EC50 = 0.047 μM) with a selectivity index of 596.