(R,E)-6-(6-(1H-indol-3-yl)-4-oxohex-2-enyl)-5,6-dihydropyran-2-one | 1572215-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R,E)-6-(6-(1H-indol-3-yl)-4-oxohex-2-enyl)-5,6-dihydropyran-2-one
• 英文别名: (2R)-2-[(E)-6-(1H-indol-3-yl)-4-oxohex-2-enyl]-2,3-dihydropyran-6-one
• CAS: 1572215-73-6
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: YCCRWJZUZPADPR-LLCTXKFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-1-((4-methoxybenzyl)oxy)hex-5-en-3-ol 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 (R,E)-6-(6-(1H-indol-3-yl)-4-oxohex-2-enyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells

  摘要：

  Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast cancer cells. All analogues have shown anti-proliferative activity, while some of them exhibited significant cytotoxicity. In assays related to cell-cycle distribution, these conjugates induced G1 cell-cycle arrest in MDA-MB-231 cells. The cell cycle arrest nature was further confirmed by examining the effect on Cyclin E and Cdk2 proteins that acts at G1-S phase transition. Immunocytochemistry assay revealed that these compounds inhibited nuclear translocation of NF-kappa B protein, thereby activation of NF-kappa B was inhibited. The expression of NF-kappa B target genes such as Cyclin D1 and Bcl-xL were severely affected. Apart from acting on NF-kappa B, these compounds also regulate class I Histone deacetylase proteins such as (HDAC-3 and 8) that have a crucial and regulatory role in cellproliferation. Simultaneously, the apoptotic inducing nature of these compounds was confirmed by activation of PARP protein, a protein that plays a key role in DNA damage and repair pathways. Among all compounds of this series 3g is the most potent compound and can be used for further studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.030

文献信息

• Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells
  作者：Debendra K. Mohapatra、D. Sai Reddy、M. Janaki Ramaiah、Sowjanya Ghosh、Vikram Pothula、Swetha Lunavath、Shine Thomas、S.N.C.V.L. Pushpa Valli、Manika Pal Bhadra、Jhillu S. Yadav

  DOI：10.1016/j.bmcl.2014.01.030

  日期：2014.3

  Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast cancer cells. All analogues have shown anti-proliferative activity, while some of them exhibited significant cytotoxicity. In assays related to cell-cycle distribution, these conjugates induced G1 cell-cycle arrest in MDA-MB-231 cells. The cell cycle arrest nature was further confirmed by examining the effect on Cyclin E and Cdk2 proteins that acts at G1-S phase transition. Immunocytochemistry assay revealed that these compounds inhibited nuclear translocation of NF-kappa B protein, thereby activation of NF-kappa B was inhibited. The expression of NF-kappa B target genes such as Cyclin D1 and Bcl-xL were severely affected. Apart from acting on NF-kappa B, these compounds also regulate class I Histone deacetylase proteins such as (HDAC-3 and 8) that have a crucial and regulatory role in cellproliferation. Simultaneously, the apoptotic inducing nature of these compounds was confirmed by activation of PARP protein, a protein that plays a key role in DNA damage and repair pathways. Among all compounds of this series 3g is the most potent compound and can be used for further studies. (C) 2014 Elsevier Ltd. All rights reserved.