Dimethyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanedioate | 927180-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Dimethyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanedioate
• 英文别名: dimethyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanedioate
• CAS: 927180-75-4
• 化学式: C₂₄H₃₀N₂O₈
• 分子量: 474.511
• InChiKey: NIKPPOZFDYWJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanedioate 在 碳酸氢钠 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.048
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 在 palladium on activated charcoal 吡啶 、 氢气 、 四氯化钛 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 Dimethyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanedioate
  参考文献：
  名称：

  Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.048

文献信息

• Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)
  作者：James J.-W. Duan、Lihua Chen、Zhonghui Lu、Bin Jiang、Naoyuki Asakawa、James E. Sheppeck、Rui-Qin Liu、Maryanne B. Covington、William Pitts、Soong-Hoon Kim、Carl P. Decicco

  DOI：10.1016/j.bmcl.2006.09.048

  日期：2007.1

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.