20172-76-3Relevant academic research and scientific papers
New alkenyl derivative from Piper malacophyllum and analogues: Antiparasitic activity against Trypanosoma cruzi and Leishmania infantum
Varela, Marina T.,Lima, Marta L.,Galuppo, Mariana K.,Tempone, Andre G.,de Oliveira, Alberto,Lago, Jo?o Henrique G.,Fernandes, Jo?o Paulo S.
, p. 1007 - 1011 (2017)
Alkylphenols isolated from Piper malacophyllum (Piperaceae), gibbilimbols A and B, showed interesting activity against the parasites Trypanosoma cruzi and Leishmania infantum. In continuation to our previous work, a new natural product from the essential
Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: Effectively carrying out oxidation reactions in sea water
Hazra, Susanta,Kushawaha, Ajay Kishor,Yadav, Deepak,Dolui, Pritam,Deb, Mayukh,Elias, Anil J.
, p. 1929 - 1934 (2019/04/29)
A simple, efficient, sustainable and economical method for the oxidation of alcohols and amines has been developed based on chloride, a sea abundant anionic catalyst for the practical synthesis of a wide range of carboxylic acids, ketones and imines. Oxidation of aromatic alcohols was carried out using NaCl (20 mol%) as the catalyst, NaOH (50 mol%) and aq. TBHP (4 equiv.) as the oxidant in 55-92% isolated yields. Oxidation of aromatic amines to imines was achieved by using only 20 mol% of NaCl and aq. TBHP (4 equiv.) in 32-93% isolated yields. The chlorine species formed during the reaction as the active oxidation catalyst has been identified as ClO2- for alcohols and ClO-/ClO2- for amines by control experiments. This method is mostly free from chromatographic purification, which makes it suitable for large-scale synthesis. We have scaled up to 30 gram scale the synthesis of carboxylic acids and imines in good yields and have also carried out efficiently this new method using filtered sea water as the solvent and catalyst.
Antiparasitic activity of new gibbilimbol analogues and SAR analysis through efficiency and statistical methods
Varela, Marina T.,Romaneli, Maiara M.,Lima, Marta L.,Borborema, Samanta E.T.,Tempone, Andre G.,Fernandes, Jo?o P.S.
, p. 31 - 41 (2018/06/29)
Chagas' disease and leishmaniasis are parasitic infections enrolled among the neglected tropical diseases, which urge for new treatments. In the search for new chemical entities as prototypes, gibbilimbols A/B have shown antiparasitic activity against Trypanosoma cruzi and Leishmania infantum, and then a set of analogues (LINS03 series) of this natural product were synthesized and evaluated in vitro against the parasites. In the present paper we reported five new compounds with activity against these protozoan parasites, and quite low cytotoxicity. Moreover, the interference of plasma membrane permeability of these analogues were also evaluated. We found that [(4-methoxyphenyl)methyl]octylamine (4) was noteworthy due to its high activity against the amastigote form of both parasites (IC50 1.3–5.8 μM) and good selectivity index. In order to unveil the SAR for this chemotype, we also presented a group efficiency analysis and PCA and HCA study, which indicated that the methoxyl provides good activity with lower cytotoxicity to mammalian cells. The results from SAR analyses suggest different mechanisms of action between the neutral and basic compounds. In summary, the analogues represent important activity against these parasites and must be prototypes for further exploitation.
