57582-42-0Relevant articles and documents
NO-Responsive vesicles as a drug delivery system
Li, Zhi-Heng,Tan, Zheng-Li,Ding, Ai-Xiang,Gong, Bing,Lu, Zhong-Lin,He, Lan
, p. 3535 - 3538 (2017)
A rationally designed amphiphile containing a hydrophobic Hantzsch ester and a hydrophilic phosphate ester was able to form vesicles in aqueous solution, and resulted in the first example of a NO-responsive drug delivery system.
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 of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent-Free System
Weber, Andressa C. H.,Batista, Thaís C.,Gon?alves, Bruno,Hack, Carolina R. L.,Porciuncula, Larissa M.,Treptow, Tamara G. M.,D’Oca, Caroline Da R. Montes,Russowsky, Dennis,D’Oca, Marcelo G. Montes
, p. 1399 - 1406 (2016/09/28)
The 1,3-dicarbonyl compounds are important building blocks to obtain products with various biological activities and technological applications. In this work, we used a simple transesterification method to develop fatty acetoacetates in a solvent-free medium using a green catalyst, sulfamic acid (NH2SO3H), under microwave irradiation. The experimental results demonstrate good yields in a short reaction time (13?min), which makes this method an efficient approach to synthesize fatty acetoacetates from a wide range of saturated, unsaturated, and polyunsaturated long chain fatty alcohols, and ricinoleic derivatives. Experiments of recycling of the catalyst were performed and no decrease in catalytic activity of sulfamic acid was observed.
Novel hybrid DHPM-fatty acids: Synthesis and activity against glioma cell growth in vitro
Treptow, Tamara G.M.,Figueiró, Fabrício,Jandrey, Elisa H.F.,Battastini, Ana M.O.,Salbego, Christianne G.,Hoppe, Juliana B.,Taborda, Priscila S.,Rosa, Sabrina B.,Piovesan, Luciana A.,Montes D'Oca, Caroline Da R.,Russowsky, Dennis,Montes D'Oca, Marcelo G.
, p. 552 - 562 (2015/04/14)
We described the first synthesis of fatty acid 3,4-dihydropyrimidinones (DHPM-fatty acids) using the Biginelli multicomponent reaction. Antiproliferative activity on two glioma cell lines (C6 rat and U-138-MG human) was also reported. The novel DHPM-fatty acids reduced glioma cell viability relative to temozolomide. Hybrid oxo-monastrol-palmitic acid was the most potent, reducing U-138-MG human cell viability by ca. 50% at 10 1/4M. In addition, the DHPM-fatty acids showed a large safety range to neural cells, represented by the organotypic hippocampal culture. These results suggest that the increased lipophilicity of DHPM-fatty acids offer a promising approach to overcoming resistance to chemotherapy and may play an important role in the development of new antitumor drugs.
Hexamethylenetetramine-mediated transesterification of β-keto esters
Ribeiro, Rodrigo S.,De Souza, Rodrigo O. M. A.,Vasconcellos, Mario L. A. A.,Oliveira, Bianca L.,Ferreira, Leonardo C.,Aguiar, Lucia C. S.
, p. 61 - 64 (2007/12/31)
Treatment of methyl or ethyl β-keto esters with primary, secondary, or tertiary alcohols in the presence of a catalytic amount of hexamethylenetetramine results in good to high yields of the corresponding esters. Georg Thieme Verlag Stuttgart.
A mild and regioselective method for α-bromination of β-keto esters and 1,3-diketones using bromodimethylsulfonium bromide (BDMS)
Khan, Abu T.,Ali, Md. Ashif,Goswami, Papori,Choudhury, Lokman H.
, p. 8961 - 8963 (2007/10/03)
Bromodimethylsulfonium bromide has been found to be an effective and regioselective reagent for α-monobromination of β-keto esters and 1,3-diketones. A wide variety of β-keto esters and 1,3-diketones undergo chemoselective α-monobromination with excellent yields at 0-5 °C or room temperature. The notable advantages of this protocol are no need of chromatographic separation, use of less hazardous reagent than molecular bromine, and no added base, Lewis acid, or other catalyst.
