14531-35-2Relevant academic research and scientific papers
Evaluation of the antioxidant activities of fatty polyhydroquinolines synthesized by Hantzsch multicomponent reactions
Brinkerhoff, Rafael Centuriao,Santa-Helena, Eduarda,Do Amaral, Paulo C.,Cabrera, Diego Da C.,Ongaratto, Renata F.,De Oliveira, Patrick M.,Da Ros Montes D'Oca, Caroline,Neves Gon?alves, Carla A.,Maia Nery, Luiz E.,Montes D'Oca, Marcelo G.
, p. 24688 - 24698 (2019/08/22)
Polyhydroquinolines (PHQs) are the unsymmetrical Hantzsch derivatives of 1,4-dihydropyridines with several biological applications. In this work, new fatty 2- and 3-substituted PHQ derivatives from different fatty acids and fatty alcohol feedstocks were synthesized at good yields via a four-component reaction (4CR). The antioxidant activities of fatty PHQs were investigated using three different antioxidant methods. The experiments showed that the compounds derived from 2-nitrobenzaldehyde and fatty palmitic (C16:0) and oleic (C18:1) chains showed better antioxidant activity. This revealed that combining the ortho NO2 group in the aromatic ring with the insertion of fatty chains in the PHQ core contributed to the antioxidant activity. However, among all the fatty PHQs tested, the fatty 2-substituted compound derived from oleyl alcohol and 2-nitrobenzaldehyde showed the highest antioxidant activity (EC50, 2.11-4.69 μM), which was similar to those of the antioxidant standards butylated hydroxytoluene (EC50, 1.98-6.47 μM) and vitamin E (EC50, 1.19-5.88 μM). In addition, this lipophilic compound showed higher antioxidant activity than the antihypertensive drug nifedipine (EC50, 49.25-126.86 μM). These results indicate that the new fatty PHQs may find novel applications as antioxidant additives.
Synthesis and antitumoral activity of novel analogues monastrol-fatty acids against glioma cells
De Oliveira, Franciele S.,De Oliveira, Patrick M.,Farias, Luana M.,Brinkerhoff, Rafael C.,Sobrinho, Rui Carlos M. A.,Treptow, Tamara M.,Montes D'Oca, Caroline R.,Marinho, Marcelo A. G.,Hort, Mariana A.,Horn, Ana P.,Russowsky, Dennis,Montes D'Oca, Marcelo G.
, p. 1282 - 1288 (2018/08/28)
Monastrol is a small cell-permeable heterocyclic molecule that is recognized as an inhibitor of mitotic kinesin Eg5. Heterocyclic-fatty acid derivatives are a new class of compounds with a broad range of biological activities. This work describes a comparative study of the in vitro antitumoral activity of a series of new long-chain monastrol analogues against rat glioblastoma cells. The novel analogues C6-substituted monastrol and oxo-monastrol were synthesized via Biginelli multicomponent condensation of fatty β-ketoester in good yields using a simple approach catalyzed by nontoxic and free-metal sulfamic acid. Following synthesis, their in vitro antitumoral activities were investigated. Notably, all analogues tested were active against rat glioblastoma cells. Superior activity was observed by analogues derived from palmitic and stearic fatty acid chains; these compounds were the most potent molecules, showing 13-fold higher potency than monastrol with IC50 values of 5.11 and 6.85 μM, respectively. These compounds could provide promising new lead derivatives for more potent antitumor drugs.
Synthesis of β-ketoesters from renewable resources and Meldrum's acid
Brinkerhoff, Rafael C.,Tarazona, Hernan F.,De Oliveira, Patrick M.,Flores, Darlene C.,Montes D'Oca, Caroline Da R.,Russowsky, Dennis,Montes D'Oca, Marcelo G.
, p. 49556 - 49559 (2014/12/10)
β-Ketoesters are valuable building blocks for the synthesis of compounds with different biological activities. In this study, a series of fatty β-ketoesters were obtained from fatty acids and Meldrum's acid using N,N-dicyclohexylcarbodiimide and dimethylaminopyridine. In addition, we demonstrate for the first time the synthesis of new fatty β-ketoesters from oleic (cis-C18:1), elaidic (trans-C18:1), ricinoleic (cis-C18:1, 12-OH), linoleic (cis,cis-C18:2), and linolenic (cis,cis,cis-C18:3) acids in good yields.
Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid
Zamyatina, Alla,Sekljic, Harald,Brade, Helmut,Kosma, Paul
, p. 12113 - 12137 (2007/10/03)
Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1,4′-bisphosphoryl as well as the related 4′-monophosphoryl derivatives of lipid A were synthesized. (R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3′ and N-acylated with (R)-3-hydroxyicosanoic acid at both glucosamine units. Efficient purification methods for highly hydrophobic long-chain tri-, tetra- and pentaacyl progenitors of lipid A have been developed. Purity and homogeneity of the synthetic target compounds were confirmed by NMR and MS-data as well as a sensitive immunostaining approach. The tetra- and pentaacyl species serve as biomedical probes to investigate the endotoxic potential of chlamydial lipid A and to clarify its role in Chlamydia associated infections. Graphical Abstract
Production of oxetanones
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, (2008/06/13)
The invention relates to a novel process for producing a compound having the formula STR1 wherein R1, R2 and X are described herein, via wherein R corresponding β-keto- and β-hydroxy-δ-lactones, as well as novel intermediates which occur in the process.
