8-t-butyldimethylsilyloxy-8-(2-naphthyl)-2-octenoic acid | 362671-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-t-butyldimethylsilyloxy-8-(2-naphthyl)-2-octenoic acid
• 英文别名: 8-[Tert-butyl(dimethyl)silyl]oxy-8-naphthalen-2-yloct-2-enoic acid
• CAS: 362671-42-9
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: CRSLAYCIKBULCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-t-butyldimethylsilyloxy-8-(2-naphthyl)-2-octenoic acid 在 盐酸 、 sodium tetrahydroborate 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 N-Hydroxy-8-hydroxy-8-(2-naphthyl)octanamide
  参考文献：
  名称：

  Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors

  摘要：

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.

  DOI：

  10.1021/jm020154k
• 作为产物：
  描述：

  6-溴-1-己烯 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium periodate 、 四氧化锇 、 sodium hydride 、 碳酸氢钠 、 magnesium 、 1,2-二溴乙烷 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 58.42h， 生成 8-t-butyldimethylsilyloxy-8-(2-naphthyl)-2-octenoic acid
  参考文献：
  名称：

  Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors

  摘要：

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.

  DOI：

  10.1021/jm020154k