15362-40-0Relevant articles and documents
Vilsmeier reagent, NaHSe and diclofenac acid chloride: One-pot synthesis of a novel selenoindolinone with potent anticancer activity
Aydillo, Carlos,Plano, Daniel,Ruberte, Ana Carolina,Sanmartín, Carmen,Sharma, Arun K.
, p. 38404 - 38408 (2020)
An effective and straightforward synthesis of 3-seleno functionalized indolinone (5) involving Vilsmeier reagent is presented. Likewise, a procedure to achieve lactamization of diclofenac with excellent yields by using hydrides is also ascertained. Compou
Stability of diclofenac sodium in the inclusion complex with β-cyclodextrin in the solid state
Cwiertnia, Barbara,Hladon, Teresa,Stobiecki, Maciej
, p. 1213 - 1218 (1999)
The aim of this study was to characterize the thermal stability of diclofenac sodium both alone and in the inclusion complex with β-cyclodextrin in the solid state, by determination of the number of the products of its decomposition, which were identified by GC-MS. The molar ratio of diclofenac sodium in the inclusion complex with β-cyclodextrin was 1:1. The decomposition of diclofenac sodium both alone and in inclusion complex with β-cyclodextrin occurred according to the first-order reaction. The HPLC of the samples thermostated at 80°C gave five products of decomposition, which were identified by GC-MS. Diclofenac sodium in the inclusion complex with β-cyclodextrin was more thermally stable. Thermal decomposition of diclofenac sodium leads to formation of five products, of which 4-chloro-10H-9-acridinone had not been reported previously in the literature.
Diclofenac n-derivatives as therapeutic agents with anti-inflammatory and anti-cancer effect
Galisteo, Alberto,Jannus, Fatin,García-García, Amalia,Aheget, Houssam,Rojas, Sara,Lupia?ez, José A.,Rodríguez-Diéguez, Antonio,Reyes-Zurita, Fernando J.,Quílez Del Moral, José F.
, (2021/05/18)
A series of diclofenac N-derivatives (2, 4, 6, 8c, 9c, 10a-c) were synthesized in order to test their anti-cancer and anti-inflammatory effects. The anticarcinogen activity has been assayed against three cancer cell lines: HT29, human colon cancer cells; Hep-G2, human hepatic cells; and B16-F10, murine melanoma cells. First, we determined the cytotoxicity of the different compounds, finding that the most effective compound was compound 8c against all cell lines and both compounds 4 and 6 in human Hep-G2 and HT29 cell lines. Compounds 4 and 8c were selected for the percentage of apoptosis determination, cell cycle distribution, and mitochondrial membrane potential measure because these products presented the lowest IC50 values in two of the three cancer cell lines assayed (B16-F10 and HepG2), and were two of the three products with lowest IC50 in HT29 cell line. Moreover, the percentages of apoptosis induction were determined for compounds 4 and 8c, showing that the highest values were between 30 to 60%. Next, the effects of these two compounds were observed on the cellular cycle, resulting in an increase in the cell population in G2/M cell cycle phase after treatment with product 8c, whereas compound 4 increased the cells in phase G0/G1, by possible differentiation process induction. Finally, to determine the possible apoptosis mechanism triggered by these compounds, mitochondrial potential was evaluated, indicating the possible activation of extrinsic apoptotic mechanism. On the other hand, we studied the anti-inflammatory effects of these diclofenac (DCF) derivatives on lipopolysaccharide (LPS) activated RAW 264.7 macrophages-monocytes murine cells by inhibition of nitric oxide (NO) production. As a first step, we determined the cytotoxicity of the synthesized compounds, as well as DCF, against these cells. Then, sub-cytotoxic concentrations were used to determine NO release at different incubation times. The greatest anti-inflammatory effect was observed for products 2, 4, 8c, 10a, 10b, and 9c at 20 μg·mL?1 concentration after 48 h of treatment, with inhibition of produced NO between 60 to 75%, and a concentration that reduces to the 50% the production of NO (IC50 NO) between 2.5 to 25 times lower than that of DCF. In this work, we synthesized and determined for the first time the anti-cancer and anti-inflammatory potential of eight diclofenac N-derivatives. In agreement with the recent evidences suggesting that inflammation may contribute to all states of tumorigenesis, the development of these new derivatives capable of inducing apoptosis and anti-inflammatory effects at very low concentrations represent new effective therapeutic strategies against these diseases.
Degradation kinetics and mechanism of diclofenac by UV/peracetic acid
Fu, Yongsheng,Liu, Yiqing,Zhang, Li
, p. 9907 - 9916 (2020/03/23)
In this work, the degradation kinetics and mechanism of diclofenac (DCF) by UV/peracetic acid (PAA) was investigated. The effects of pH, PAA dose and common water components such as inorganic ions and dissolved organic matter (DOM) on DCF degradation by UV/PAA were also evaluated. It was observed that the addition of PAA promoted the photodegradation of DCF due to the generation of reactive radicals in the photolysis of PAA, which was also confirmed by the radical scavenging experiment. The best degradation efficiency of DCF was obtained at pH 8.5. The removal of DCF was enhanced gradually with increasing PAA dose. Since NO3- is a photosensitive substance which can generate HO under UV irradiation, its existence promoted the degradation of DCF. The presence of CO32- could slightly improve DCF degradation, which might be due to the role of generated carbonate radicals. Cl-, SO42- and Fe3+ had little effect on DCF removal, while Cu2+ could enhance DCF degradation because of its catalytic ability for PAA decomposition. An inhibition effect on DCF removal was observed in the presence of DOM, and it was more obvious in higher concentration of DOM. The elimination of total organic carbon (TOC) was low. According to the twelve reaction products detected in the UV/PAA system, the probable transformation mechanism of DCF was proposed exhibiting eight reaction pathways, i.e., hydroxylation, decarboxylation, formylation, dehydrogenation, dechlorination-hydrogenation, dechlorination-cyclization, dechlorination-hydroxylation and amidation. This study indicates that UV/PAA is a promising method for DCF removal from contaminated water.