96251-92-2Relevant academic research and scientific papers
Sequential Functionalization of meta-C-H and ipso-C-O Bonds of Phenols
Xu, Jiancong,Chen, Jingjing,Gao, Feng,Xie, Shuguang,Xu, Xiaohua,Jin, Zhong,Yu, Jin-Quan
, p. 1903 - 1907 (2019)
The use of a template as a linchpin motif in directed remote C-H functionalization is a versatile yet relatively underexplored strategy. We have developed a template-directed approach to realizing one-pot sequential palladium-catalyzed meta-selective C-H olefination of phenols, and nickel-catalyzed ipso-C-O activation and arylation. Thus, this bifunctional template converts phenols to synthetically useful 1,3-disubstituted arenes.
Development and Application of a Chemical Probe Based on a Neuroprotective Flavonoid Hybrid for Target Identification Using Activity-Based Protein Profiling
Gunesch, Sandra,Soriano-Castell, David,Lamer, Stephanie,Schlosser, Andreas,Maher, Pamela,Decker, Michael
, p. 3823 - 3837 (2020/11/16)
Alzheimer's disease (AD) is the most common form of dementia, and up to now, there are no disease-modifying drugs available. Natural product hybrids based on the flavonoid taxifolin and phenolic acids have shown a promising pleiotropic neuroprotective profile in cell culture assays and even disease-modifying effects in vivo. However, the detailed mechanisms of action remain unclear. To elucidate the distinct intracellular targets of 7-O-esters of taxifolin, we present in this work the development and application of a chemical probe, 7-O-cinnamoyltaxifolin-alkyne, for target identification using activity-based protein profiling. 7-O-Cinnamoyltaxifolin-alkyne remained neuroprotective in all cell culture assays. Western blot analysis showed a comparable influence on the same intracellular pathways as that of the lead compound 7-O-cinnamoyltaxifolin, thereby confirming its suitability as a probe for target identification experiments. Affinity pulldown and MS analysis revealed adenine nucleotide translocase 1 (ANT-1) and sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) as intracellular interaction partners of 7-O-cinnamoyltaxifolin-alkyne and thus of 7-O-esters of taxifolin.
Benzocarbazoles dioxane derivatives, its preparation process and its use in medicine
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Paragraph 0539; 0541-0544, (2016/10/10)
The invention relates to a benzodioxane derivative, a preparation method thereof and application of the derivative in medicines. Specifically, the invention relates to a novel benzodioxane derivative shown as a formula (I), medial salt thereof or a medicine composition containing the derivative, and a preparation method of the derivative. The invention further relates to a use of the benzodioxane derivative and the medial salt thereof or the medicine composition containing the derivative in preparing therapeutic agent, especially GPR 40 agonist, and a drug for treating the diseases such as diabetes, metabolic disorders and the like, wherein each substituent group in the formula (I) is as defined in the description.
COMPOSITIONS FOR THE TREATMENT OF KIDNEY AND/OR LIVER DISEASE
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Paragraph 0086, (2016/10/04)
The present invention relates to novel compounds and their use in the prophylactic and/or therapeutic treatment of kidney and/or liver disease.
Synthesis and anticancer activities of glycyrrhetinic acid derivatives
Li, Yang,Feng, Ling,Song, Zhi-Fang,Li, Hai-Bei,Huai, Qi-Yong
, (2016/05/09)
A total of forty novel glycyrrhetinic acid (GA) derivatives were designed and synthesized. The cytotoxic activity of the novel compounds was tested against two human breast cancer cell lines (MCF-7, MDA-MB-231) in vitro by the MTT method. The evaluation results revealed that, in comparison with GA, compound 42 shows the most promising anticancer activity (IC50 1.88 ± 0.20 and 1.37 ± 0.18 μM for MCF-7 and MDA-MB-231, respectively) and merits further exploration as a new anticancer agent.
Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship
Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le
, p. 255 - 262 (2015/04/22)
This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.
NOVEL METAL FREE PROCESS FOR ALLYLIC OXIDATION
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Page/Page column 15, (2015/02/25)
The patent discloses a novel metal free process for the preparation of corresponding phenol and ketone via allylic oxidation of substituted cyclohexenes. Air is used as oxidant in the present process and can be used as such or optionally selected from pure oxygen or atmospheric oxygen. Moreover, the process of the present invention utilizes easily available starting materials and is a green eco-friendly, convenient and economical process with high yield of >60 % and high selectivity
Design and synthesis of small molecule RhoA inhibitors: A new promising therapy for cardiovascular diseases?
Deng, Jing,Feng, Enguang,Ma, Sheng,Zhang, Yan,Liu, Xiaofeng,Li, Honglin,Huang, Huang,Zhu, Jin,Zhu, Weiliang,Shen, Xu,Miao, Liyan,Liu, Hong,Jiang, Hualiang,Li, Jian
experimental part, p. 4508 - 4522 (2011/09/14)
RhoA is a member of Rho GTPases, a subgroup of the Ras superfamily of small GTP-binding proteins. RhoA, as an important regulator of diverse cellular signaling pathways, plays significant roles in cytoskeletal organization, transcription, and cell-cycle progression. The RhoA/ROCK inhibitors have emerged as a new promising treatment for cardiovascular diseases. However, to date, RhoA inhibitors are macromolecules, and to our knowledge, small molecular-based inhibitors have not been reported. In this study, a series of first-in-class small molecular RhoA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. Virtual screening of ～200,000 compounds, followed by SPR-based binding affinity assays resulted in three compounds with binding affinities to RhoA at the micromolar level (compounds 1-3). Compound 1 was selected for further structure modifications in considering binding activity and synthesis ease. Fourty-one new compounds (1, 12a-v, 13a-h, and 14a-j) were designed and synthesized accordingly. It was found that eight (12a, 12j, 14a, 14b, 14d, 14e, 14 g, and 14h) showed high RhoA inhibition activities with IC50 values of 1.24 to 3.00 μM. A pharmacological assay indicated that two compounds (14g and 14 h) demonstrated noticeable vasorelaxation effects against PE-induced contraction in thoracic aorta artery rings and served as good leads for developing more potent cardiovascular agents.
Ligustrazine derivatives. Part 5: Design, synthesis and biological evaluation of novel ligustrazinyloxy-cinnamic acid derivatives as potent cardiovascular agents
Chen, Hongfei,Li, Guoning,Zhan, Peng,Liu, Xinyong
experimental part, p. 5609 - 5615 (2012/01/03)
A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H2O2)-induced oxidative damage on ECV-304 cells. Some compounds exhibited high activity in one or both of the assays, of which, compound 2e displayed the highest protective effect on the proliferation of the damaged ECV-304 cells (EC 50 = 0.020 mM), and compound 2f was the most active anti-platelet aggregation agent (EC50 = 0.054 mM). Structure-activity relationships were briefly discussed.
Microwave-accelerated Wittig olefination of β-chloroacroleins
Bera, Rabin,Dhananjaya,Singh, Shambu Nath,Kumar, Rajender,Mukkanti,Pal, Manojit
experimental part, p. 1300 - 1305 (2009/04/18)
The first microwave assisted Wittig reactions of β-chloroacroleins with a stabilized ylide are described here. A combination of sodium ethoxide and toluene was found to be optimum and using this reaction condition a number of alkenyl-substituted benzopyra
