铁死亡激活剂Erastin的合成
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摘要
对铁诱导的细胞死亡激活剂Erastin的合成工艺进行改进,以2-氨基苯甲酸为起始原料,通过5步反应合成了Erastin,产率31.4%,纯度98.33%,其结构经~1H NMR和MS(ESI)确证。
The preparation process of the ferroptosis-induced cell death activator Erastin was improved. Erastin was synthesized through five steps using 2-aminobenzoic acid as starting material. The total yield was 31.4% and the purity was 98.33%. The structure was confirmed by ~1H NMR and MS(ESI).
The preparation process of the ferroptosis-induced cell death activator Erastin was improved. Erastin was synthesized through five steps using 2-aminobenzoic acid as starting material. The total yield was 31.4% and the purity was 98.33%. The structure was confirmed by ~1H NMR and MS(ESI).
引文
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[4] WANG D, PENG Y, XIE Y, et al. Antiferroptotic activity of non-oxidative dopamine[J].Biochem Biophys Res Commun,2016,480(4):602-607.
[5] MüLLER T, DEWITZ C, SCHMITZ J, et al. Necroptosis and ferroptosis are alternative celldeath pathways that operate in acute kidney failure[J].Cell Mol Life Sci,2017,74(19):3631-3645.
[6] DOLMA S, LESSNICK S L, HAHN W C, et al. Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells[J].Cancer Cell,2003,3(3):285-296.
[7] XIE Y, HOU W, SONG X, et al. Ferroptosis:Process and function[J].Cell Death And Differentiation,2016,23:369-379.
[8] YU Y, XIE Y, CAO L, et al. The ferroptosis inducer erastin enhances sensitivity of acute myeloid leukemia cells to chemotherapeutic agents[J].Molecular & Cellular Oncology,2015,2(4):e1054549.
[9] SHINTOKU R, TAKIGAWA Y, YAMADA K, et al. Lipoxygenase-mediated generation of lipid peroxides enhances ferroptosis induced by erastin and RSL3[J].Cancer Sci,2017,108(11):2187-2194.
[10] CODENOTTI S, POLI M, ASPERTI M, et al. Cell growth potential drives ferroptosis susceptibility in rhabdomyosarcoma and myoblast cell lines[J].J Cancer Res Clin,2018,144(9):1717-1760.
[11] WANG Y, CHANG S, WU Q, et al. The protective role of mitochondrial ferritin on erastin-induced ferroptosis[J].Front Aging Neurosci,2016,8:308.
[12] COLEMAN PAUL J, FRALER MARK E, HOFFMAN WILLIAM F. Mitotic kinesin inhibitors:WO 2004039774A2[P].2004.
[13] BECKLIN R, CHEPANOSKE L, PELTER M, et al. Erastin and erastin binding proteins, and uses thereof:WO 2006081331A2[P].2006.
[14] STOCKWELL, BRENT R. Compounds and compositions that cause non-apoptotic cell death and uses thereof:WO 2009108384A2[P].2009.
[15] YAN D, XIANG Y, LI K, et al. Synthesis,characterization and properties of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives and their europium complexes[J].J Mol Struct,2014,1074(3):487-495.
[16] BRENT R. Erastin analogs and uses thereof:US 20070161644A1[P].2007.
[17] RAD-MOGHADAM K, ROUGI S. Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4H-3,1-benzoxazin-4-ones[J].Beilstein J Org Chem,2009,5(13):1-4.
[2] DIXON S J, LEMBERG K M, LAMPRECHT M R, et al. Ferroptosis:An iron-dependent form of nonapoptotic cell death[J].CELL,2012,149(5):1060-1072.
[3] MINGHUI G, XUEJUN J. To eat or not to eat-the metabolic flavor of ferroptosis[J].Current Opinion In Cell Biology,2018,51:58-64.
[4] WANG D, PENG Y, XIE Y, et al. Antiferroptotic activity of non-oxidative dopamine[J].Biochem Biophys Res Commun,2016,480(4):602-607.
[5] MüLLER T, DEWITZ C, SCHMITZ J, et al. Necroptosis and ferroptosis are alternative celldeath pathways that operate in acute kidney failure[J].Cell Mol Life Sci,2017,74(19):3631-3645.
[6] DOLMA S, LESSNICK S L, HAHN W C, et al. Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells[J].Cancer Cell,2003,3(3):285-296.
[7] XIE Y, HOU W, SONG X, et al. Ferroptosis:Process and function[J].Cell Death And Differentiation,2016,23:369-379.
[8] YU Y, XIE Y, CAO L, et al. The ferroptosis inducer erastin enhances sensitivity of acute myeloid leukemia cells to chemotherapeutic agents[J].Molecular & Cellular Oncology,2015,2(4):e1054549.
[9] SHINTOKU R, TAKIGAWA Y, YAMADA K, et al. Lipoxygenase-mediated generation of lipid peroxides enhances ferroptosis induced by erastin and RSL3[J].Cancer Sci,2017,108(11):2187-2194.
[10] CODENOTTI S, POLI M, ASPERTI M, et al. Cell growth potential drives ferroptosis susceptibility in rhabdomyosarcoma and myoblast cell lines[J].J Cancer Res Clin,2018,144(9):1717-1760.
[11] WANG Y, CHANG S, WU Q, et al. The protective role of mitochondrial ferritin on erastin-induced ferroptosis[J].Front Aging Neurosci,2016,8:308.
[12] COLEMAN PAUL J, FRALER MARK E, HOFFMAN WILLIAM F. Mitotic kinesin inhibitors:WO 2004039774A2[P].2004.
[13] BECKLIN R, CHEPANOSKE L, PELTER M, et al. Erastin and erastin binding proteins, and uses thereof:WO 2006081331A2[P].2006.
[14] STOCKWELL, BRENT R. Compounds and compositions that cause non-apoptotic cell death and uses thereof:WO 2009108384A2[P].2009.
[15] YAN D, XIANG Y, LI K, et al. Synthesis,characterization and properties of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives and their europium complexes[J].J Mol Struct,2014,1074(3):487-495.
[16] BRENT R. Erastin analogs and uses thereof:US 20070161644A1[P].2007.
[17] RAD-MOGHADAM K, ROUGI S. Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4H-3,1-benzoxazin-4-ones[J].Beilstein J Org Chem,2009,5(13):1-4.