2150-52-9Relevant academic research and scientific papers
Photoinduced Synthesis of Benzannulated Spiroketals
Chen, Xinzheng,Wang, Sasa
, p. 2042 - 2046 (2015)
A range of benzannulated spiroketals were prepared through photoinduced enone isomerization and spiroketalization as key steps. The simple protocol requires no additional reagents or catalyst, and tolerates both moisture and air.
Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo
Wang, Ziqing,Mu, Wenwen,Li, Pengxiao,Liu, Guoyun,Yang, Jie
, (2021/02/21)
Curcumin was reported as an anti-inflammatory agent. However, curcumin's poor bioavailability limited its clinical utility. Here, thirty ortho-substituted mono-carbonyl curcumin derivatives, containing acetone, cyclopentanone, cyclohexanone or 4-piperidione (N—H, N-methyl or N-acrylyl) moieties replacing β-diketone moiety of curcumin, were investigated for anti-inflammatory activity. Two active ortho-trifluoromethoxy-substituted 4-piperidione-containing derivatives 22 and 24 owned good cell uptake ability, and displayed excellent anti-inflammatory activity in both lipopolysaccharide-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. They inhibited the production of nitric oxide, reactive oxygen species, malonic dialdehyde and cyclooxygenase-2; and the expression of pro-inflammatory cytokines interleukin-1β, tumor necrosis factor-α and myeloperoxidase; the phosphorylation of mitogen-activated protein kinases; and the nucleus translocation of p65. What's more, 22 or 24 oral administered reduced the severity of clinical symptoms of ulcerative colitis (body weight and disease activity index), and reduced obviously DSS-induced colonic pathological damage (the colon length and histopathology analysis). These results suggested that ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives 22 and 24 were potential anti-inflammatory agents; and offered the important information for design and discovery of more potent anti-inflammatory drug candidates.
Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
, (2020/01/21)
Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
Anti-proliferative effect and induction of apoptosis in androgen-independent human prostate cancer cells by 1,5-bis(2-hydroxyphenyl)-1,4-pentadiene-3-one
Citalingam, Kamini,Othman, Iekhsan,Naidu, Rakesh,Abas, Faridah,Lajis, Nordin H.
, p. 3406 - 3430 (2015/07/15)
Curcumin has poor in vivo absorption and bioavailability, highlighting a need for new curcumin analogues with better characteristics in these aspects. The aim of this study is to determine the anti-cancer properties of four selected curcumin analogues, on the cytotoxicity, proliferative and apoptotic effects on androgen-independent human prostate cancer cells (PC-3 and DU 145). Initial cytotoxicity screening showed MS17 has the highest cell inhibitory effect, with EC50 values of 4.4 ± 0.3 and 4.1 ± 0.8 μM, followed by MS13 (7.5 ± 0.1 and 7.4 ± 2.6 μM), MS49 (14.5 ± 1.2 and 12.3 ± 2.3 μM) and MS40E (28.0 ± 7.8 and 30.3 ± 1.9 μM) for PC-3 and DU 145 cells, respectively. Time-dependent analysis also revealed that MS13 and MS17 displayed a greater anti-proliferative effect than the other compounds. MS17 was chosen based on the high selectivity index value for further analysis on the morphological and biochemical hallmarks of apoptosis. Fluorescence microscopy analysis revealed apoptotic changes in both treated prostate cancer cells. Relative caspase-3 activity increased significantly at 48 h in PC-3 and 12 h in DU 145 cells. Highest enrichment of free nucleosomes was noted at 48 h after treatment with MS17. In conclusion, MS17 demonstrated anti-proliferative effect and induces apoptosis in a time and dose-dependent manner suggesting its potential for development as an anti-cancer agent for androgen-independent prostate cancer.
The curcumin analogue 1,5-bis(2-hydroxyphenyl)-1,4-pentadiene-3-one induces apoptosis and downregulates E6 and E7 oncogene expression in HPV16 and HPV18-infected cervical cancer cells
Paulraj, Felicia,Abas, Faridah,Lajis, Nordin H.,Othman, Iekhsan,Hassan, Sharifah Syed,Naidu, Rakesh
, p. 11830 - 11860 (2015/08/11)
In an effort to study curcumin analogues as an alternative to improve the therapeutic efficacy of curcumin, we screened the cytotoxic potential of four diarylpentanoids using the HeLa and CaSki cervical cancer cell lines. Determination of their EC50 values indicated relatively higher potency of 1,5-bis(2-hydroxyphenyl)-1,4-pentadiene-3-one (MS17, 1.03 ± 0.5 μM; 2.6 ± 0.9 μM) and 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (MS13, 2.8 ± 0.4; 6.7 ± 2.4 μM) in CaSki and HeLa, respectively, with significantly greater growth inhibition at 48 and 72 h of treatment compared to the other analogues or curcumin. Based on cytotoxic and anti-proliferative activity, MS17 was selected for comprehensive apoptotic studies. At 24 h of treatment, fluorescence microscopy detected that MS17-exposed cells exhibited significant morphological changes consistent with apoptosis, corroborated by an increase in nucleosomal enrichment due to DNA fragmentation in HeLa and CaSki cells and activation of caspase-3 activity in CaSki cells. Quantitative real-time PCR also detected significant down-regulation of HPV18- and HPV16-associated E6 and E7 oncogene expression following treatment. The overall data suggests that MS17 treatment has cytotoxic, anti-proliferative and apoptosis-inducing potential in HPV-positive cervical cancer cells. Furthermore, its role in down-regulation of HPV-associated oncogenes responsible for cancer progression merits further investigation into its chemotherapeutic role for cervical cancer.
Catalytic asymmetric synthesis of aromatic spiroketals by spinphox/iridium(I)-catalyzed hydrogenation and spiroketalization of α,α′-Bis(2-hydroxyarylidene) ketones
Wang, Xiaoming,Han, Zhaobin,Wang, Zheng,Ding, Kuiling
supporting information; experimental part, p. 936 - 940 (2012/03/08)
From spiro to spiro: An iridium(I) complex with a spiral P,N ligand (SpinPhox) is highly efficient in the catalytic asymmetric hydrogenation of α,α′-bis(2-hydroxyarylidene) ketones to afford the corresponding aromatic spiroketals in high yields with excellent diastereo- and enantioselectivities (see scheme). The complex plays a dual role in the reaction, acting as catalyst for both the hydrogenation of C=C bonds and the subsequent spiroketalization of bisphenolic ketones. Copyright
Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors
Hosoya, Takahiro,Nakata, Asami,Yamasaki, Fumie,Abas, Faridah,Shaari, Khozirah,Lajis, Nordin Hj,Morita, Hiroshi
experimental part, p. 166 - 176 (2012/05/20)
Anti-melanogenesis screening of 47 synthesized curcumin-like diarylpentanoid analogues was performed to show that some had a potent inhibitory effect on the melanogenesis in B16 melanoma cells. Their actions were considered to be mostly due to tyrosinase inhibition, tyrosinase expression inhibition, and melanin pigment degradation. The structure-activity relationships of those curcumin-like diarylpentanoid analogues which inhibited the melanogenesis and tyrosinase activity were also discussed. Of those compounds assayed, (2E,6E)-2,6-bis(2,5- dimethoxybenzylidene)cyclohexanone showed the most potent anti-melanogenesis effect, the mechanism of which is considered to be the degradation of the melanin pigment in B16 melanoma cells, affecting neither the tyrosinase activity nor tyrosinase expression. The Japanese Society of Pharmacognosy and Springer 2011.
Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
Jantan, Ibrahim,Bukhari, Syed Nasir Abbas,Lajis, Nordin Haji,Abas, Faridah,Wai, Lam Kok,Jasamai, Malina
experimental part, p. 404 - 412 (2012/07/02)
Objectives A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro. Methods The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique. Key findings Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration. Conclusions The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.
Di(ortho-hydroxybenzylidene)acetone as a new acid-base indicator and a chromogenic receptor for anions and guanidine
Goswami, Shyamaprosad,Chakrabarty, Rinku
experimental part, p. 547 - 557 (2012/03/26)
The development of a new simple acid-base indicator di(o- hydroxybenzylidene)acetone (1) is reported as a possible alternative to phenolphthalein and its performance has been compared with those of o-hydroxybenzylideneacetone (2) and p-hydroxybenzylideneacetone (3), two synthetic compounds, and curcumin (4), a natural product occurring in turmeric. Among the four compounds, 1 is found to be the best. It may also be used in the titration of guanidine in non-aqueous solvents (e.g. in dry alcohol). It is also shown to be a chemosensor for anions.
1,5-bis (2-hydroxyphenyl)pent-1,4-diene-3-one: A lead compound for the development of broad-spectrum antibacterial agents
Rani,Jain, Sapna,Kumar, Rita,Kumar, Anil
experimental part, p. 31 - 35 (2011/07/31)
A systematic and comparative study has been made starting from a naturally-occurring chalcone nucleus to design effective antibacterial agents. The present investigation established 1,5-bis(2-hydroxyphenyl)pent-1,4-diene-3- one (1c) as a lead compound with potential against a panel of pathogenic bacterial strains. Staphylococcus (coagulase negative), Escherichia coli, Pseudomonas aeruginosa, Acenetobacter sp. and Klebsiella pneumoniae. Gentamycine and tetracycline were used as reference drugs. The mode of antibacterial action of Ic was also studied by scanning electron microscopy, which showed membrane disruption and cell lysis of the organisms during the exposure of the tested compound. In vitro toxicity tests demonstrated that all the bioactive compounds showed far less toxicity against human erythrocytes.
