6515-05-5Relevant articles and documents
Synthesis and Anti-inflammatory Evaluation of (R)-, (S)-, and (±)-Sanjuanolide Isolated from Dalea frutescens
Fang, Bo,Xiao, Zhongxiang,Qiu, Yinda,Shu, Sheng,Chen, Xianxin,Chen, Xiaojing,Zhuang, Fei,Zhao, Yunjie,Liang, Guang,Liu, Zhiguo
, p. 748 - 755 (2019)
The known chalcone (±)-sanjuanolide (1) can be isolated from Dalea frutescens. This study presents a convergent strategy for the first total synthesis of (R)-, (S)-, and (±)-sanjuanolide (1). The key step for synthesizing (R)- and (S)-1 was a Corey-Bakshi
The discovery of novel sanjuanolide derivatives as chemotherapeutic agents targeting castration-resistant prostate cancer
Wang, Guangbao,Chen, Xiaojing,Wang, Nan,Xiao, Yunbei,Shu, Sheng,Alsayed, Ali Mohammed Mohammed,Liu, Lu,Ma, Yue,Liu, Peng,Zhang, Qianwen,Chen, Xiangjuan,Liu, Zhiguo,Zheng, Xiaohui
, (2021)
There remains a critical need for more effective therapies for the treatment of castration-resistant prostate cancer (CRPC), which is the leading cause of death in patients with prostate cancer. In this study, a series of sanjuanolide derivatives were des
Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells
Selvaraj, Baskar,Kim, Dae Won,Huh, Gyuwon,Lee, Heesu,Kang, Kyungsu,Lee, Jae Wook
, (2020/03/05)
Glutamate-induced neurotoxicity is characterized by cellular Ca2+ uptake, which is upstream of reactive oxygen species (ROS)-induced apoptosis signaling and MAPKs activation. In the present study, we synthesized isoliquiritigenin analogs with electron-donating and electron-withdrawing functional groups. These analogs were evaluated for neuroprotective effect against glutamate-induced neurotoxicity in HT22 cells. Among these analogs, compound BS11 was selected as a potent neuroprotective agent. Cellular Ca2+ concentration, ROS level, MAPKs activation and AIF translocation to the nucleus were increased upon treatment with 5 mM glutamate. In contrast, we identified that compound BS11 reduced the cellular Ca2+ concentration and ROS level upon glutamate exposure. Western blot analysis showed that MAPK activation was decreased by treatment with compound BS11. We further identified that cotreatment of compound BS11 and glutamate inhibited translocation of AIF to the nucleus.
Synthesis method of 4-isopropylresorcinol
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Paragraph 0018; 0031-0032; 0036-0037; 0041-0042, (2018/04/01)
The invention discloses a synthesis method of 4-isopropylresorcinol. The method comprises the following steps: group protection, Grignard reaction, hydrodeoxygenation and deprotection. According to the method, a novel protecting group halomethyl methyl ether is adopted for protecting phenolic hydroxy, then the Grignard reaction is performed on 3 milliliters of methylmagnesium chloride or methylmagnesium bromide, hydrogenation is performed under low pressure and normal temperature in the presence of acid, and the protecting group is removed with hydrochloric acid to obtain the 4-isopropylresorcinol. The problem of difficulty in treatment after Witting reaction is solved, the temperature and the pressure of hydrogenation reaction are reduced, the hydrogenation time is shortened, deprotectionis finally implemented under a mild condition, and the whole process is a safe production process capable of implementing industrial production.
Design, synthesis and bioactivity of chalcones and its analogues
Niu, Chao,Tuerxuntayi, Adila,Li, Gen,Kabas, Madina,Dong, Chang-Zhi,Aisa, Haji Akber
, p. 1533 - 1538 (2017/07/17)
The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.
3,5-b isopentene base, 2, 4, 4 '-three hydroxy chalcone and its derivatives use and preparation
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Paragraph 0030; 0032; 0033, (2016/11/28)
The invention discloses 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone as well as use and a preparation method of derivatives of the 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone, belonging to the field of a preparation method and anti-tumor activity measu
Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers
Hofmann, Emily,Webster, Jonathan,Do, Thuy,Kline, Reid,Snider, Lindsey,Hauser, Quintin,Higginbottom, Grace,Campbell, Austin,Ma, Lili,Paula, Stefan
, p. 578 - 587 (2016/02/09)
In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.
Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs
Wang, Hao-Meng,Zhang, Li,Liu, Jiang,Yang, Zhao-Liang,Zhao, Hong-Ye,Yang, Yao,Shen, Di,Lu, Kui,Fan, Zhen-Chuan,Yao, Qing-Wei,Zhang, Yong-Min,Teng, Yu-Ou,Peng, Yu
, p. 439 - 448 (2015/03/05)
Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by 1H NMR, 13C NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 50-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 mM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis.
Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions
Wang, Haomeng,Yan, Zhihong,Lei, Yanan,Sheng, Kai,Yao, Qingwei,Lu, Kui,Yu, Peng
supporting information, p. 897 - 899 (2014/02/14)
Four natural chalcones bearing prenyl or geranyl groups, i.e., isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2′,4′,4-trihydroxy-5′-geranylchalcone (isoxanthoangelol, 4) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. Among them, the first total synthesis of 2′,4′,4-trihydroxy-5′-geranylchalcone was achieved in 36% overall yield. Comparing with the reported methods based on C-alkylation or O-alkylation followed by Claisen rearrangement to introduce the side chain, this new strategy capitalizes on a precious regiochemical control during iodination. The overall yields for the synthesis of the first three chalcones were improved from 17% to 53%, 12% to 35%, and 28% to 50%, respectively.
Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions
Wang, Haomeng,Yan, Zhihong,Lei, Yanan,Sheng, Kai,Yao, Qingwei,Lu, Kui,Yu, Peng
supporting information, p. 897 - 899 (2015/03/03)
Four natural chalcones bearing prenyl or geranyl groups, i.e., isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2′,4′,4-trihydroxy-5′-geranylchalcone (isoxanthoangelol, 4) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. Among them, the first total synthesis of 2′,4′,4-trihydroxy-5′-geranylchalcone was achieved in 36% overall yield. Comparing with the reported methods based on C-alkylation or O-alkylation followed by Claisen rearrangement to introduce the side chain, this new strategy capitalizes on a precious regiochemical control during iodination. The overall yields for the synthesis of the first three chalcones were improved from 17% to 53%, 12% to 35%, and 28% to 50%, respectively.
