117-02-2Relevant articles and documents
Synthesis of an anthraquinone derivative (DHAQC) and its effect on induction of G2/M arrest and apoptosis in breast cancer MCF-7 cell line
Yeap, Sweekeong,Akhtar, Muhammad Nadeem,Lim, Kian Lam,Abu, Nadiah,Ho, Wan Yong,Zareen, Seema,Roohani, Kiarash,Ky, Huynh,Tan, Sheau Wei,Lajis, Nordin,Alitheen, Noorjahan Banu
, p. 983 - 992 (2015)
Anthraquinones are an important class of naturally occurring biologically active compounds. In this study, anthraquinone derivative 1,3-dihydroxy-9,10-anthraquinone-2-carboxylic acid (DHAQC) (2) was synthesized with 32% yield through the FriedelCrafts condensation reaction. The mechanisms of cytotoxicity of DHAQC (2) in human breast cancer MCF-7 cells were further investigated. Results from the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that DHAQC (2) exhibited potential cytotoxicity and selectivity in the MCF-7 cell line, comparable with the naturally occurring anthraquinone damnacanthal. DHAQC (2) showed a slightly higher IC50 (inhibitory concentration with 50% cell viability) value in the MCF-7 cell line compared to damnacanthal, but it is more selective in terms of the ratio of IC50 on MCF-7 cells and normal MCF-10A cells. (selective index for DHAQC (2) was 2.3 and 1.7 for damnacanthal). The flow cytometry cell cycle analysis on the MCF-7 cell line treated with the IC50 dose of DHAQC (2) for 48 hours showed that DHAQC (2) arrested MCF-7 cell line at the G2/M phase in association with an inhibited expression of PLK1 genes. Western blot analysis also indicated that the DHAQC (2) increased BAX, p53, and cytochrome c levels in MCF-7 cells, which subsequently activated apoptosis as observed in annexin V/propidium iodide and cell cycle analyses. These results indicate that DHAQC (2) is a synthetic, cytotoxic, and selective anthraquinone, which is less toxic than the natural product damnacanthal, and which demonstrates potential in the induction of apoptosis in the breast cancer MCF-7 cell line.
Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances
Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng
, (2020)
The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.
Method for continuously producing 2, 6-dihydroxytoluene
-
, (2021/08/11)
The invention discloses a method for continuously producing 2, 6-dihydroxytoluene. According to the method, 3-chloro-2-methylaniline is taken as a raw material, diazotization is carried out through a micro-channel reactor to synthesize an intermediate 3-chloro-2-methylphenol, and then 2, 6-dihydroxytoluene is synthesized. According to the method, the micro-channel reactor is used for diazotization of 3-chloro-2-methylaniline so that severe heat release and unstable properties of the product in the reaction process can be effectively avoided, the retention time is short, the next reaction is directly carried out after the reaction is finished, the continuous reaction can be experimented, the yield of the diazotization step can be increased to 85-95% from the traditional 75-85%, the total yield of the 2, 6-dihydroxytoluene is increased to 80-90%, and the product purity can be up to more than or equal to 99.0%.
Method for synthesizing 2,6-dihydroxytoluene by using waste acid
-
, (2021/08/07)
The invention discloses a method for synthesizing 2,6-dihydroxytoluene by using waste acid mechanically. According to the method, 3-chloro-2-methylaniline is taken as a raw material, an intermediate 3-chloro-2-methylphenol is synthesized through diazotization and hydrolysis, the reaction is optimized in the alkali fusion, acidification and refining processes, the mechanical application of waste acid and a solvent in the reaction and the optimization of a refining scheme are emphatically optimized, the yield is effectively improved, three wastes are reduced, and 2,6-dihydroxytoluene is synthesized. The method provided by the invention greatly reduces the generation of acidic wastewater, better meets the requirement of environmental protection, and effectively increases the yield of the product, and the quality of the product reaches 99.0-99.5%.
Rubiadin A ring glycosylated derivative as well as preparation method and application of Rubiadin A ring glycosylated derivative
-
Paragraph 0081; 0083-0084, (2020/11/26)
The invention provides a Rubiadin A ring glycosylated derivative as well as a preparation method and application thereof, and belongs to the technical field of medicines. The invention provides a Rubiadin A ring glycosylated derivative with a structure shown as a formula I, the derivative can serve as a vascular endothelial growth factor receptor 1 (VEGFR1) agonist to act on VEGFR1 in a targetingmode, meanwhile, a Notch2/Hey1 signal channel is activated, a JNK/p38 signal channel is inhibited, and the effect of treating fatty liver is achieved.
Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues
Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu
, p. 10042 - 10055 (2013/09/23)
Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
Saha, Koushik,Lam, Kok Wai,Abas, Faridah,Sazali Hamzah,Stanslas, Johnson,Hui, Lim Siang,Lajis, Nordin H.
, p. 2093 - 2104 (2013/07/26)
Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 μM. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.
Naturally Occurring Rubiadins. A Caveat
Boisvert, Louise,Brassard, Paul
, p. 1055 - 1058 (2007/10/02)
A number of typical rubiadins have been prepared by unambiguous means, and their characteristics reveal that the structures of most natural products so designated are erroneous.
