ethyl 6-[2-[2-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]oxyethyl]-2-[(Z)-6-trimethylsilylhex-3-en-1,5-diynyl]-2H-pyridine-1-carboxylate | 173483-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 6-[2-[2-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]oxyethyl]-2-[(Z)-6-trimethylsilylhex-3-en-1,5-diynyl]-2H-pyridine-1-carboxylate
• CAS: 173483-42-6
• 化学式: C₃₃H₃₁N₃O₈Si
• 分子量: 625.71
• InChiKey: BTLQHTZKKVNKIU-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 6-[2-[2-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]oxyethyl]-2-[(Z)-6-trimethylsilylhex-3-en-1,5-diynyl]-2H-pyridine-1-carboxylate 在 potassium fluoride 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以88%的产率得到ethyl 2-[(Z)-hex-3-en-1,5-diynyl]-6-[2-[2-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]oxyethyl]-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Enediynes as Antitumor Compounds:  Synthesis of Tetrahydropyridine Derivatives

  摘要：

  Enediyne anticancer antibiotics are a rapidly emerging class of compounds derived from natural sources. Many synthetic approaches for the construction of simpler compounds containing this pharmacophore have recently been published. Most of these approaches use the quinoline ring as the heterocyclic moiety. In this paper, we describe a synthetic route for the preparation of enediyne systems 14 and 15, which include in their structure a tetrahydropyridine ring and are related to dynemicin A. Their stereochemistries were determined using NOESY and COSY-NMR. Finally, compounds derived from linkage to intercalating carriers, such as a fluorene ring to enediyne 15 or a naphthalimide ring to acyclic enediyne 6, were prepared.

  DOI：

  10.1021/jo951188l
• 作为产物：
  描述：

  6-<2-(tert-butyldimethylsilyloxy)ethyl>-2-ethynyl-1-(ethoxycarbonyl)-1,2-dihydropyridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 氢氟酸 、 正丁胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 ethyl 6-[2-[2-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]oxyethyl]-2-[(Z)-6-trimethylsilylhex-3-en-1,5-diynyl]-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Enediynes as Antitumor Compounds:  Synthesis of Tetrahydropyridine Derivatives

  摘要：

  Enediyne anticancer antibiotics are a rapidly emerging class of compounds derived from natural sources. Many synthetic approaches for the construction of simpler compounds containing this pharmacophore have recently been published. Most of these approaches use the quinoline ring as the heterocyclic moiety. In this paper, we describe a synthetic route for the preparation of enediyne systems 14 and 15, which include in their structure a tetrahydropyridine ring and are related to dynemicin A. Their stereochemistries were determined using NOESY and COSY-NMR. Finally, compounds derived from linkage to intercalating carriers, such as a fluorene ring to enediyne 15 or a naphthalimide ring to acyclic enediyne 6, were prepared.

  DOI：

  10.1021/jo951188l

文献信息

• Enediynes as Antitumor Compounds:  Synthesis of Tetrahydropyridine Derivatives
  作者：Miguel F. Braña、Marina Morán、María Jesús Pérez de Vega、Isabel Pita-Romero

  DOI：10.1021/jo951188l

  日期：1996.1.1

  Enediyne anticancer antibiotics are a rapidly emerging class of compounds derived from natural sources. Many synthetic approaches for the construction of simpler compounds containing this pharmacophore have recently been published. Most of these approaches use the quinoline ring as the heterocyclic moiety. In this paper, we describe a synthetic route for the preparation of enediyne systems 14 and 15, which include in their structure a tetrahydropyridine ring and are related to dynemicin A. Their stereochemistries were determined using NOESY and COSY-NMR. Finally, compounds derived from linkage to intercalating carriers, such as a fluorene ring to enediyne 15 or a naphthalimide ring to acyclic enediyne 6, were prepared.