1-Ethyl-4-[(E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-piperazine | 872701-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-Ethyl-4-[(E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-piperazine
• 英文别名: 1-ethyl-4-[(E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyl]piperazine
• CAS: 872701-11-6
• 化学式: C₁₆H₃₁BN₂O₂
• 分子量: 294.245
• InChiKey: QENMBOXFIVZZGU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Ethyl-4-[(E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-piperazine 、 4-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]phenyl}-amino)-7-[(1E)-3-hydroxyprop-1-enyl]quinoline-3-carbonitrile 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 4-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]phenyl}-amino)-7-[(1E)-4-(4-ethylpiperazin-1-yl)but-1-enyl]quinoline-3-carbonitrile
  参考文献：
  名称：

  4-Anilino-7-alkenylquinoline-3-carbonitriles as potent MEK1 kinase inhibitors

  摘要：

  A series of substituted 7-alkenyl 4[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-3-quinolinecarbonitrile analogs were synthesized and evaluated as MEK1 kinase inhibitors. The synthetic details, structure-activity relationships, biological activity, and selected oral exposure studies of these analogs are described. From these studies, compound 5m was chosen as a strong candidate for further evaluation. The selectivity of 5m was ascertained against a panel of 17 kinases, where activity was observed against EGFR, Src, Lyn, and IR kinases. Western blot studies in WM-266 cells demonstrated that 5m inhibited phosphorylation of ERK, while additional kinase pathways tested showed no inhibition at up to 10 mu M of 5m. PK studies, as well as a xenograft and in vivo biomarker studies are described for 5m. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.009
• 作为产物：
  描述：

  1-but-3-ynyl-4-ethyl-piperazine 、 频那醇硼烷 在 Schwartz's reagent 作用下， 反应 24.0h， 生成 1-Ethyl-4-[(E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-piperazine
  参考文献：
  名称：

  4-Anilino-7-alkenylquinoline-3-carbonitriles as potent MEK1 kinase inhibitors

  摘要：

  A series of substituted 7-alkenyl 4[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-3-quinolinecarbonitrile analogs were synthesized and evaluated as MEK1 kinase inhibitors. The synthetic details, structure-activity relationships, biological activity, and selected oral exposure studies of these analogs are described. From these studies, compound 5m was chosen as a strong candidate for further evaluation. The selectivity of 5m was ascertained against a panel of 17 kinases, where activity was observed against EGFR, Src, Lyn, and IR kinases. Western blot studies in WM-266 cells demonstrated that 5m inhibited phosphorylation of ERK, while additional kinase pathways tested showed no inhibition at up to 10 mu M of 5m. PK studies, as well as a xenograft and in vivo biomarker studies are described for 5m. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.009

文献信息

• Zr-Mediated hydroboration: stereoselective synthesis of vinyl boronic esters
  作者：Yanong D. Wang、Gregory Kimball、Amar S. Prashad、Yan Wang

  DOI：10.1016/j.tetlet.2005.10.031

  日期：2005.12

  An improved process for the preparation of (E)-vinylboronic esters via a Zr-mediated hydroboration of alkynes, especially oxygen-containing alkynes, is described. (c) 2005 Published by Elsevier Ltd.