3,4-dicarboethoxybenzothienyl[1,2-a]-dibenzothiophene | 192707-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3,4-dicarboethoxybenzothienyl[1,2-a]-dibenzothiophene
• 英文别名: Diethyl 3,20-dithiapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1,4,6,8,10,12,14,16,18-nonaene-11,12-dicarboxylate
• CAS: 192707-02-1
• 化学式: C₂₄H₁₈O₄S₂
• 分子量: 434.537
• InChiKey: WBUXNKFXNOIULG-UHFFFAOYSA-N

物化性质

• 熔点：
  206-207 °C
• 沸点：
  608.4±50.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-dicarboethoxybenzothienyl[1,2-a]-dibenzothiophene 在 甲醇 、 氰化钠 、 六甲基二硅氮烷 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 C₂₀H₉NO₂S₂
  参考文献：
  名称：

  Synthesis and Mixed Lineage Kinase Activity of Pyrrolocarbazole and Isoindolone Analogs of (+)K-252a

  摘要：

  Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.

  DOI：

  10.1021/jm051074u
• 作为产物：
  描述：

  2,2'-bibenzo[b]thiophene 、 丁炔二酸二乙酯 在 2,6-二叔丁基-4-甲基苯酚 作用下， 反应 24.0h， 以45%的产率得到3,4-dicarboethoxybenzothienyl[1,2-a]-dibenzothiophene
  参考文献：
  名称：

  Synthesis and Mixed Lineage Kinase Activity of Pyrrolocarbazole and Isoindolone Analogs of (+)K-252a

  摘要：

  Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.

  DOI：

  10.1021/jm051074u

文献信息

• Synthesis and Mixed Lineage Kinase Activity of Pyrrolocarbazole and Isoindolone Analogs of (+)K-252a
  作者：Robert L. Hudkins、Neil W. Johnson、Thelma S. Angeles、George W. Gessner、John P. Mallamo

  DOI：10.1021/jm051074u

  日期：2007.2.8

  Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.