(3Z,6Z)-3-[(5-叔丁基-1H-咪唑-4-基)亚甲基]-6-(苯亚甲基)-2,5-哌嗪二酮

• 常用名: (3Z,6Z)-3-[(5-叔丁基-1H-咪唑-4-基)亚甲基]-6-(苯亚甲基)-2,5-哌嗪二酮
• 英文名: Plinabulin (NPI-2358)
• CAS号: 714272-27-2
• 分子量: 336.388
• 密度: 1.3±0.1 g/cm3
• 沸点: 730.3±60.0 °C at 760 mmHg
• 分子式: C₁₉H₂₀N₄O₂
• 熔点: N/A
• 闪点: 395.5±32.9 °C

用途

Plinabulin (NPI-2358)是一种VDA,能结合微管蛋白的秋水仙碱结合位点,IC50为9.8-18 nM。

名称

• 中文名: (3Z,6Z)-3-[(5-叔丁基-1H-咪唑-4-基)亚甲基]-6-(苯亚甲基)-2,5-哌嗪二酮
• 英文名: (3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
• 中文别名: 普那布林

生物活性

• 描述: Plinabulin (NPI-2358)是一种VDA,能结合微管蛋白的秋水仙碱结合位点,IC50为9.8-18 nM。
• 相关类别:
  信号通路 >> 细胞周期/DNA损伤 >> 微管/微管蛋白
  信号通路 >> 细胞骨架 >> 微管/微管蛋白
  研究领域 >> 癌症
• 参考文献:

  [1]. Nicholson B et al. NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anticancer Drugs. 2006 Jan;17(1):25-31.

  [2]. Monica M. Mita et al. Phase 1 First-in-Human Trial of the Vascular Disrupting Agent Plinabulin (NPI-2358) in Patients with Solid Tumors or Lymphomas Clin Cancer Res December 1, 2010 16; 5892

  [3]. Yakushiji F, Tanaka H, Muguruma K, Iwahashi T, Yamazaki Y, Hayashi Y.,Prodrug study of plinabulin using a click strategy focused on the effects of a replaceable water-solubilizing moiety.,Chem Pharm Bull (Tokyo). 2012;60(7):877-81.

  [4]. Yamazaki Y, Sumikura M, Masuda Y, Hayashi Y, Yasui H, Kiso Y, Chinen T, Usui T, Yakushiji F, Potts B, Neuteboom S, Palladino M, Lloyd GK, Hayashi Y.,Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents.,Bioorg Med Chem. 2012 Jul 15;20(14):4279-89. Epub 2012 Jun 4.

  [5]. Bertelsen LB, Shen YY, Nielsen T, St?dkilde-J?rgensen H, Lloyd GK, Siemann DW, Horsman MR.,Vascular effects of plinabulin (NPI-2358) and the influence on tumour response when given alone or combined with radiation.Int J Radiat Biol. 2011 Nov;87(11):1126-34.

物理化学性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 730.3±60.0 °C at 760 mmHg
• 分子式: C₁₉H₂₀N₄O₂
• 分子量: 336.388
• 闪点: 395.5±32.9 °C
• 精确质量: 336.158630
• PSA: 94.92000
• LogP: 2.66
• InChIKey: UNRCMCRRFYFGFX-TYPNBTCFSA-N
• SMILES: CC(C)(C)c1[nH]cnc1C=c1[nH]c(=O)c(=Cc2ccccc2)[nH]c1=O
• 蒸汽压: 0.0±2.4 mmHg at 25°C
• 折射率: 1.657
• 储存条件: 室温，干燥

靶点实验

查看更多实验

实验名称：Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Cac... 来源：ChEMBL 靶标：Severe acute respiratory syndrome coronavirus 2 External Id：CHEMBL4303805

实验名称：Induction of multipolar spindle formation in human HeLa cells at 20 to 30 nM by DAPI ... 来源：ChEMBL 靶标：HeLa External Id：CHEMBL3383011

实验名称：Inhibition of mitotic spindle formation in human HeLa cells at 20 to 70 nM by DAPI st... 来源：ChEMBL 靶标：HeLa External Id：CHEMBL3383010

实验名称：Cytotoxicity against human NCI-H1975 cells assessed as reduction in cell viability af... 来源：ChEMBL 靶标：NCI-H1975 External Id：CHEMBL3294430

实验名称：Cytotoxicity against human HeLa cells assessed as reduction in cell viability after 7... 来源：ChEMBL 靶标：HeLa External Id：CHEMBL3294665

实验名称：Cytotoxicity against human BGC823 cells assessed as reduction in cell viability after... 来源：ChEMBL 靶标：NON-PROTEIN TARGET External Id：CHEMBL3294664

实验名称：SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response f... 来源：ChEMBL 靶标：Replicase polyprotein 1ab External Id：CHEMBL4495582

实验名称：Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 7... 来源：ChEMBL 靶标：MCF7 External Id：CHEMBL3294667

实验名称：Cytotoxicity against human HuH7 cells assessed as reduction in cell viability after 7... 来源：ChEMBL 靶标：NON-PROTEIN TARGET External Id：CHEMBL3294666

实验名称：Cytotoxicity against HUVEC after 48 hrs using resazurin by microplate fluorometer ana... 来源：ChEMBL 靶标：HUVEC External Id：CHEMBL2027127

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英文别名

• NPI-2358/KPU-2
• Plinabulin,NPI2358,NPI-2358
• Plinabulin
• S1176_Selleck
• Plinabulin,NPI2358
• NPI 2358
• Plinabulin [USAN:INN]
• (3Z,6Z)-3-Benzylidene-6-{[4-(2-methyl-2-propanyl)-1H-imidazol-5-yl]methylene}-2,5-piperazinedione
• 3-Z-benzylidene-6-(5"-tert-butyl-1H-imidazol-4"-Z-ylmethylene)-piperazine-2,5-dione
• 3-(Z)-benzylidene-6-(((Z)-5-tert-butyl-1H-imidazol-4-yl)methylene)-piperazine-2,5-dione
• tert-butyl-dehydrophenylahistin