186534-02-1Relevant articles and documents
Synthesis of colletotrichumine A
Varnava, Kyriakos G.,Sperry, Jonathan
, p. 335 - 336 (2015)
A short synthesis of colletotrichumine A, an oxindole-pyrazine alkaloid isolated from the pathogenic fungus Colletotrichum capsici, is described.
Discovery of potential anticancer multi-targeted ligustrazine based cyclohexanone and oxime analogs overcoming the cancer multidrug resistance
Zha, Gao-Feng,Qin, Hua-Li,Youssif, Bahaa G.M.,Amjad, Muhammad Wahab,Raja, Maria Abdul Ghafoor,Abdelazeem, Ahmed H.,Bukhari, Syed Nasir Abbas
, p. 34 - 48 (2017)
The drug research and development nowadays is focusing on multi-target drugs. In the treatment of cancer, therapies using drugs inhibiting one numerous targets signify a novel viewpoint. In comparison with traditional therapy, multi-targeted drugs directly aim cell subpopulations which are involved in progression of tumor. The current study comprises the synthesis of 34 novel ligustrazine-containing α, β-unsaturated carbonyl-based compounds and oximes. The growth of 5 various cancer cell types was strongly inhibited by ligustrazine-containing oximes as revealed by biological evaluation. A strong SAR was provided by the antiproliferative activity. The mechanistic effects of most active antiproliferative compounds on tubulin polymerization, EGFR TK kinases, KAF and BRAFV600E were investigated, followed by in?vitro investigation of reversal of efflux-based resistance developed by cancer cells. EGFR was strongly inhibited by two oximes 7e and 8o. Out of all linkers including positive control, 1-isopropyl-piperidin-4-one linker-bearing compounds showed best inhibition of FAK. The strongest inhibitory activity of BRAFV600E was showed by compound 5e with an IC50 of 0.7?μM. Analogs such as 5 and 7 (b,e,f) exhibited a dual role as anticancer as well as MDR reversal agents. For understanding the target protein integrations with new compounds, molecular docking studies were also carried out.
Synthesis and relationship of stability and biological activity of new DSS and TMP conjugates
Sun, Yewei,Tan, Zicheng,Liang, Zhibin,Wang, Liang,Shan, Luchen,Yu, Pei,Lee, Simon Mingyuen,Wang, Yuqiang
, p. 586 - 591 (2015)
A series of novel conjugates of danshensu (DSS) and tetramethylpyrazine (TMP) were designed and synthesized. Their stability toward hydrolysis by carboxylesterase and cardioprotective effect against t-BHP- and doxorubicin-induced damage were evaluated in H9c2 cells. The results revealed that increasing steric hindrance with bulky groups at the linkage position between DSS and TMP prolonged the half-life and also markedly increased the protective effect. Compound 7 was the most potent in protecting against t-BHP- and doxorubicin-induced damage. The protective effect of compound 7 may in part be attributed to its promotion of mitochondrial biogenesis. This journal is
Synthesis and biological evaluation of ligustrazine derivatives
Zhang, Chao,Chen, Lang-Di,Liang, Xin-Tong,Liu, Wei-Xiong,Wu, Wen-Hao
, p. 114 - 117 (2017)
Synthesized ligustrazine derivatives (1a, 1b, 1c (novel)) were structurally confirmed by mass spectrometry,1H NMR, and 13C NMR. The cytotoxic activities of all derivatives were evaluated by MTS assay in three human prostate cancer cell lines (PC-3, LNCaP, and DU145) and in the A549 human lung cancer cell line. Compound 1a exhibited strong cytotoxic activity against PC-3 cells (IC50 3.63μM). In addition, compounds 1-1c showed moderate α1-adrenergic receptor (AR) subselective antagonistic and β2-AR agonistic effects, indicating potential use for the treatment of chronic obstructive pulmonary disease. Molecular docking results showed 1b bound to one region of the active site in β2-AR, but 1, 1a, and 1c bound to a different region.
Synthesis and biological evaluation of novel ligustrazine-chalcone derivatives as potential anti-triple negative breast cancer agents
Chen, Shaobin,Huang, Jianan,Huang, Qinghui,Li, Yuanzhi,Luo, Yingqi,Wang, Chengxu,Wu, Wenhao,Yu, Lihong,Zha, Dailong,Zhang, Chao,Zhang, Jianye,Zhou, Wenmin
, (2021/07/21)
A series of novel ligustrazine-chalcone hybrids were synthesized and evaluated for their in vitro and in vivo antitumor activities. The results showed that most of these compounds exhibited significant in vitro cytotoxicity against MDA-MB-231, MCF-7, A549
Discovery of a new tetramethylpyrazine based chalcone with α, β-unsaturated ketone moiety as a potential anticancer agent
Bukhari, Syed Nasir Abbas
, p. 826 - 829 (2020/02/25)
In this study, a new ligustrazine-based chalcone molecule has been synthesized that contains an extra α, β-Unsaturated ketone moiety along with α, the β-Unsaturated carbonyl group of chalone. A new tetramethylpyrazine (TMP) based aldehyde was synthesized to make the TMP (ligustrazine) as part of chalcone and then it was reacted with newly synthesized ketone containing additional α, β-Unsaturated ketone moiety. After characterization, this new compound was evaluated for its effect on different types of cancer cell lines and very promising results were obtained. The growth of these cancer cells was inhibited by newly designed and synthesized compounds, especially for colon and pancreatic cancer cells with IC50 0.04-0.05 μM.
TRIFLUOROACETYL HYDRAZIDE COMPOUNDS AND MEDICAL USES THEREOF
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, (2019/07/29)
The present invention relates to trifluoroacetyl hydrazide compounds and medical uses thereof. The compounds have a structure of the following formula: The compounds showed multifunctional mechanisms, including inhibition of glutamate excitotoxicity, activation of MEF2 transcriptional activity, clearance of free radicals, and promotion of nerve differentiation, and has a better protective effect on cells especially nerve cells. The compound can be used to prepare prophylactic or therapeutic medicaments with cytoprotective effects, for the prevention or treatment of diseases related to glutamate receptor activation, MEF2 disorders or excessive free radicals generation. The diseases include, for example, neurodegenerative diseases such as Alzheimer's disease, Parkinson and stroke, and the free radicals related diseases such as heart disease, myocardial ischemia, diabetes and other cardiovascular and cerebrovascular diseases.
Chloroxime compound as well as preparation method and application thereof in pharmacy
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, (2019/08/20)
The invention relates to a chloroxime compound, its preparation method and application in pharmacy. The chloroxime compound has a structure shown as the general formula I in the specification. The compounds has a very strong effect in synergistic regulation of heat shock protein activity, can be used for treating neurodegenerative diseases caused by injection of Abeta1-42 to rats, and aims to treat human neurodegenerative diseases. The compound also has a significant stress resistant effect, and can be used for preparation of new drugs treating diseases caused by protein misfolding and/or aggregation, and oxidative stress.
Novel Ligustrazine-Based Analogs of Piperlongumine Potently Suppress Proliferation and Metastasis of Colorectal Cancer Cells in Vitro and in Vivo
Zou, Yu,Zhao, Di,Yan, Chang,Ji, Yanpeng,Liu, Jin,Xu, Jinyi,Lai, Yisheng,Tian, Jide,Zhang, Yihua,Huang, Zhangjian
, p. 1821 - 1832 (2018/03/21)
Piperlongumine 1 increases reactive oxygen species (ROS) levels and preferably induces cancer cell apoptosis by triggering different pathways. However, the poor solubility of 1 limits its intensive investigation and clinical application. Ligustrazine possesses a water-soluble pyrazine skeleton and can inhibit proliferation and metastasis of cancer cells. We synthesized compound 3 by replacement of the trimethoxyphenyl of 1 with ligustrazine moiety and further introduced 2-Cl, -Br, and -I to 3 for synthesis of 4-6, respectively. Compound 4 possessed 14-fold greater aqueous solubility than 1 and increased ROS levels in colorectal cancer HCT-116 cells. Additionally, 4 preferably inhibited proliferation, migration, invasion, and heteroadhesion of HCT-116 cells. Treatment with 4 suppressed tumor growth and lung metastasis in vivo and prolonged the survival of tumor-bearing mice. Furthermore, 4 mitigated TGF-β1-induced epithelial-mesenchymal transition and Wnt/β-catenin activation by inhibiting the Akt and GSK-3β phosphorylation in HCT-116 cells. Collectively, 4 displayed significant antiproliferation and antimetastasis activities, superior to 1.
Ligustrazine chalcone compound and preparation method and application thereof
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, (2018/09/21)
The invention relates to a ligustrazine chalcone compound and a preparation method and application thereof. The ligustrazine chalcone compound is an antioxidant with a series of novel structure, and better antioxidation activities are shown by most of compounds, so that the ligustrazine chalcone compound has further studying and developing value, and the ligustrazine chalcone compound can be usedas a lead compound of the antioxidant. The invention further provides the application of preparing antioxidation medicines of the compound and a composition containing one or more compounds.