3-(oct-7-enyl)pyridine | 941298-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(oct-7-enyl)pyridine
• 英文别名: 3-Oct-7-enylpyridine
• CAS: 941298-76-6
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: HTIJZCSKKOSCFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(13-chlorotridecyl)-1-(oct-7-enyl)pyridinium chloride 、 3-(oct-7-enyl)pyridine 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到1-(oct-7-enyl)-3-{13-[1-(oct-7-enyl)pyridinium-1-yl]tridecyl}pyridinium chloride iodide
  参考文献：
  名称：

  Bispyridinium Dienes:  Histone Deacetylase Inhibitors with Selective Activities

  摘要：

  A novel synthetic route to the cyclostellettamines 1 using as the key step a microwave-mediated macrocyclic ring-closing metathesis of precursors bispyridinium dienes 10 followed by catalytic hydrogenation has been developed. The open-chain bispyridinium dienes 10 showed uniformly higher histone deacetylase (HDAC) inhibitory potency than the natural products. Diene 10b inhibited HDAC1 and was inactive on HDAC4, whereas 10a showed a weak inhibition of HDAC1 and a higher activity on HDAC4. Neither 10b nor 10a inhibited isoforms HDAC2 and HDAC3. Cell cycle analysis, cell differentiation, and apoptosis as well as evaluation of the acetylation status of H3 lysine tails, up-regulation of p21(WAF1/CIP1), and R-tubulin acetylation induced by the dienes 10 and cyclostellettamines 1 were also carried out on the human leukemia U937 cell line. These enzymatic and functional assays suggest that 10b is a HDAC1-selective inhibitor and 10a is a HDAC subclass IIa-selective inhibitor.

  DOI：

  10.1021/jm070028m
• 作为产物：
  描述：

  3-甲基吡啶 、 7-溴-1-庚烯 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 3-(oct-7-enyl)pyridine
  参考文献：
  名称：

  Bispyridinium Dienes:  Histone Deacetylase Inhibitors with Selective Activities

  摘要：

  A novel synthetic route to the cyclostellettamines 1 using as the key step a microwave-mediated macrocyclic ring-closing metathesis of precursors bispyridinium dienes 10 followed by catalytic hydrogenation has been developed. The open-chain bispyridinium dienes 10 showed uniformly higher histone deacetylase (HDAC) inhibitory potency than the natural products. Diene 10b inhibited HDAC1 and was inactive on HDAC4, whereas 10a showed a weak inhibition of HDAC1 and a higher activity on HDAC4. Neither 10b nor 10a inhibited isoforms HDAC2 and HDAC3. Cell cycle analysis, cell differentiation, and apoptosis as well as evaluation of the acetylation status of H3 lysine tails, up-regulation of p21(WAF1/CIP1), and R-tubulin acetylation induced by the dienes 10 and cyclostellettamines 1 were also carried out on the human leukemia U937 cell line. These enzymatic and functional assays suggest that 10b is a HDAC1-selective inhibitor and 10a is a HDAC subclass IIa-selective inhibitor.

  DOI：

  10.1021/jm070028m

文献信息

• Bispyridinium Dienes:  Histone Deacetylase Inhibitors with Selective Activities
  作者：Carlos Pérez-Balado、Angela Nebbioso、Paula Rodríguez-Graña、Annunziata Minichiello、Marco Miceli、Lucia Altucci、Ángel R. de Lera

  DOI：10.1021/jm070028m

  日期：2007.5.1

  A novel synthetic route to the cyclostellettamines 1 using as the key step a microwave-mediated macrocyclic ring-closing metathesis of precursors bispyridinium dienes 10 followed by catalytic hydrogenation has been developed. The open-chain bispyridinium dienes 10 showed uniformly higher histone deacetylase (HDAC) inhibitory potency than the natural products. Diene 10b inhibited HDAC1 and was inactive on HDAC4, whereas 10a showed a weak inhibition of HDAC1 and a higher activity on HDAC4. Neither 10b nor 10a inhibited isoforms HDAC2 and HDAC3. Cell cycle analysis, cell differentiation, and apoptosis as well as evaluation of the acetylation status of H3 lysine tails, up-regulation of p21(WAF1/CIP1), and R-tubulin acetylation induced by the dienes 10 and cyclostellettamines 1 were also carried out on the human leukemia U937 cell line. These enzymatic and functional assays suggest that 10b is a HDAC1-selective inhibitor and 10a is a HDAC subclass IIa-selective inhibitor.