N-(2,4-diiodophenyl)methanesulfonamide | 1537178-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,4-diiodophenyl)methanesulfonamide
• CAS: 1537178-16-7
• 化学式: C₇H₇I₂NO₂S
• 分子量: 423.013
• InChiKey: KXQWBWOMWBNKJR-UHFFFAOYSA-N

物化性质

• 沸点：
  415.0±55.0 °C(Predicted)
• 密度：
  2.430±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2,4-diiodophenyl)methanesulfonamide 、 3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以60%的产率得到3-(2-((5-iodo-1-(methylsulfonyl)-1H-indol-2-yl)methoxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 2H- 1,3-benzoxazin-4(3 H )-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B

  摘要：

  A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy) ethyl}-2H-benzo[e][1,3] oxazin-4(3H)-one using 10% Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 lM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.117

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.