(Z)-4-((6-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide | 1538580-67-4

• 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)-4-((6-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
• 英文别名: 6-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]hexyl 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetate
• CAS: 1538580-67-4
• 化学式: C₃₄H₃₃FN₂O₉S₂
• 分子量: 696.774
• InChiKey: SSXZABOZSNPRPE-BRPDVVIDSA-N

物化性质

• 熔点：
  60-63 °C
• 沸点：
  883.5±75.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Sulindac 在 4-二甲氨基吡啶 、 Oxone 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (Z)-4-((6-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  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

• Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment
  作者：Andrew Nortcliffe、Alexander G. Ekstrom、James R. Black、James A. Ross、Fouad K. Habib、Nigel P. Botting、David O’Hagan

  DOI：10.1016/j.bmc.2013.12.014

  日期：2014.1

  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.