(Z)-N-(2-aminoethyl)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide | 944159-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (Z)-N-(2-aminoethyl)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide
• 英文别名: N-[2-(dimethylamino)ethyl]-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetamide
• CAS: 944159-19-7
• 化学式: C₂₂H₂₃FN₂O₂S
• 分子量: 398.501
• InChiKey: JFGAFWIWVHWKAF-ODLFYWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-N-(2-aminoethyl)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide 、 N-((4-nitrophenoxy)carbonyl)-3-phenylsydnonimine 以 乙腈 为溶剂， 反应 24.0h， 以86%的产率得到N-((2-(2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamido)ethoxy)carbamoyl)-3-phenylsydnonimine
  参考文献：
  名称：

  Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

  摘要：

  A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 +/- 4.1 and 12.1 +/- 3.2 mu M, respectively, coupled with observed nitric oxide release. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.014
• 作为产物：
  描述：

  Sulindac 、 乙二胺 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以81%的产率得到(Z)-N-(2-aminoethyl)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

  摘要：

  A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 +/- 4.1 and 12.1 +/- 3.2 mu M, respectively, coupled with observed nitric oxide release. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.014

文献信息

• WO2007/81694
  申请人：——

  公开号：——

  公开（公告）日：——
• Derivatives of sulindac, use thereof and preparation thereof
  申请人：Piazza Gary

  公开号：US20070244122A1

  公开（公告）日：2007-10-18

  Derivatives of sulindac are provided along with pharmaceutical compositions containing them and use for precancerous conditions and treating cancer. Derivatives of sulindac are also suitable for treating chronic inflammatory conditions. A method for preparing the derivatives is also provided.
• US8044048B2
  申请人：——

  公开号：US8044048B2

  公开（公告）日：2011-10-25