2-chloro-3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine | 1465900-98-4

• 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: 2-chloro-3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine
• 英文别名: 2-Chloro-3-[prop-2-ynoxy(thiophen-2-yl)methyl]pyridine；2-chloro-3-[prop-2-ynoxy(thiophen-2-yl)methyl]pyridine
• CAS: 1465900-98-4
• 化学式: C₁₃H₁₀ClNOS
• 分子量: 263.748
• InChiKey: GYHTZRWMMXAIHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-硝基碘苯 、 2-chloro-3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine 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88%的产率得到2-chloro-3-((3-(2-nitrophenyl)prop-2-ynyloxy)(thiophen-2-yl)methyl)pyridine
  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
• 作为产物：
  描述：

  2-氯-3-吡啶甲醛 在 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 14.0h， 生成 2-chloro-3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine
  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

文献信息

• Synthesis of indole based novel small molecules and their in vitro anti-proliferative effects on various cancer cell lines
  作者：Balakrishna Dulla、E. Sailaja、Upendar Reddy CH、Madhu Aeluri、Arunasree M. Kalle、S. Bhavani、D. Rambabu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.12.050

  日期：2014.1

  Indole based novel small molecules were designed as potential anticancer agents. Multi step synthesis of these compounds was carried out by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The single crystal X-ray diffraction study was used to confirm the molecular structure of a representative compound unambiguously. Many of these compounds were evaluated for their anti-proliferative properties in vitro against six cancer cell lines as well as noncancerous cells. All these compounds showed selective growth inhibition of cancer cells and several of them were found to be promising with IC50 values in the range of 0.1-1.2 mu M, comparable to the known anticancer drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.
• 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
  作者：Upendar Reddy Chamakura、E. Sailaja、Balakrishna Dulla、Arunasree M. Kalle、S. Bhavani、D. Rambabu、Ravikumar Kapavarapu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.bmcl.2014.01.044

  日期：2014.3

  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.