ethyl 3-iodo-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate | 1569288-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl 3-iodo-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate
• CAS: 1569288-42-1
• 化学式: C₁₀H₁₁IO₂S
• 分子量: 322.167
• InChiKey: GTFKBGNXZBXOJV-UHFFFAOYSA-N

物化性质

• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.746±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloro-3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine 、 ethyl 3-iodo-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 12.5h， 以85%的产率得到ethyl 3-(3-[(2-chloropyridin-3-yl)(thiophen-2-yl)methoxy]prop-1-ynyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro anti-proliferative effects of 3-(hetero)aryl substituted 3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine derivatives on various cancer cell lines

  摘要：

  A series of 3-(hetero) aryl substituted 3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine derivatives were designed as potential anticancer agents. These compounds were conveniently prepared by using Pd/C-Cu mediated Sonogashira type coupling as a key step. Many of these compounds were found to be promising when tested for their in vitro anti-proliferative properties against six cancer cell lines. All these compounds were found to be selective towards the growth inhibition of cancer cells with IC50 values in the range of 0.9-1.7 mu M (against MDA-MB 231 and MCF7 cells), comparable to the known anticancer drug doxorubicin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.044