112605-49-9Relevant academic research and scientific papers
Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
, p. 1052 - 1072 (2017)
We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 μM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines (4m and 4o) showed excellent profiles in the treatment of L. amazonensis-infected macrophages, reducing the parasite burden by more than 95% in tested concentrations.
1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
, p. 981 - 986 (2017)
We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50??15.0?μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity toward murine macrophages, except 17 and 18, which presented good selective indexes (SI?≥?10.0). The five more active compounds (2, 3, 13, 17, and 18) were selected for the treatment of infected macrophages, and all of them were able to reduce the number of internalized parasites by more than 80%, as well as the number of infected macrophages by more than 70% in at least one of the tested concentrations. Altogether, these results demonstrate the potential of these compounds as new hits of antileishmanial agents and open future possibilities for them to be tested in in vivo studies.
Synthesis of the first lariat crown-formazan, prototype of a new series of podandocoronands
Katritzky, Alan R.,Belyakov, Sergie A.,Dupont Durst
, p. 6465 - 6468 (1994)
Crown-formazan (1) with a pendant hydroxy group was obtained by a phase- transfer assisted azo-coupling reaction. Acylation of the hydroxy group of (1) with 2-chloroacetyl chloride followed by reaction with dimethylamine afforded 13-[2-(N,N-dimethylamino)
Regioselective cleavage of 2-aryloxymethyloxiranes to 3-aryloxy-l- halogenopropan-2-ols
Maciejewski,Poltorak,Kaminska
experimental part, p. 595 - 604 (2009/12/26)
A series of new 2-ary loxymethy loxiranes prepared from epichlorohydrin and substituted phenols was subjected to nucleophilic opening of the oxirane ring. A comparison of regioselectivity and product yield for oxirane cleavage by means of aqueous hydrohalogenic acids or lithium tetrahalogenocuprates under anhydrous conditions was performed. The latter method provided very high regioselectivity for 3-aryloxy-l-halo-genopropan-2-ols as well as excellent yields.
SYNTHESIS OF MACROHETEROCYCLIC ANALOGS OF DIBENZO-CROWN COMPOUNDS. 6. HYDROXYLATED 16-MEMBERED OXAAZA-CROWN COMPOUNDS
Formanovskii, A. A.,Mikhura, I. V.
, p. 227 - 231 (2007/10/02)
High-dilution cycloacylation of 2-acetoxy-1,3-bis-(2-aminophenoxy)propane with the diacid chlorides of glutaric, diglycolic, thiodiglycolic, and N-tosyliminodiacetic acids gives the macrocyclic diamides.Subsequent reduction with boron hydride affords 16-m
