(3R)-1-oxohex-5-en-3-yl acrylate | 1198569-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-1-oxohex-5-en-3-yl acrylate
• 英文别名: [(3R)-1-oxohex-5-en-3-yl] prop-2-enoate
• CAS: 1198569-79-7
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: CCMHKWPNIQOQER-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-1-oxohex-5-en-3-yl acrylate 在 Grubbs catalyst first generation 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (S,E)-6-(4-oxo-6-(3-phenoxyphenyl)hex-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
• 作为产物：
  描述：

  (R)-1-((4-methoxybenzyl)oxy)hex-5-en-3-ol 在 4-二甲氨基吡啶 、 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 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (3R)-1-oxohex-5-en-3-yl acrylate
  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

• A Concise and Efficient Synthesis of (5R,7S)-Kurzilactone and Its (5S,7R)-Enantiomer by the Mukaiyama Aldol Reaction
  作者：Gowravaram Sabitha、Peddabuddi Gopal、C. Reddy、Jhillu Yadav

  DOI：10.1055/s-0029-1216936

  日期：2009.10

  Natural kurzilactone (5R,7S) and its (5S,7R)-enantiomer were synthesized by a convergent approach using a diastereoselective Mukaiyama aldol reaction to construct the anti diol unit. Finally, a ring-closing metathesis reaction led to the target molecule. kurzilactone - Mukaiyama reaction - aldol reaction - ring closure - metathesis

  使用非对映选择性Mukaiyama aldol反应通过收敛方法合成天然kurzilactone（5 R，7 S）及其（5 S，7 R）-对映异构体，以构建抗二醇单元。最后，闭环复分解反应产生了靶分子。 kurzilactone-Mukaiyama反应-aldol反应-闭环-复分解
• Total Syntheses and Cytotoxic Evaluations of Cryptolactones A<sub>1</sub>, A<sub>2</sub>, B<sub>1</sub>, B<sub>2</sub>, and Their Derivatives
  作者：Makoto Inai、Yuki Oguri、Mitsuyo Horikawa、Hiroto Kaku、Shinya Suzuki、Kei Kitamura、Tetsuto Tsunoda

  DOI：10.1248/cpb.c19-01114

  日期：2020.4.1

  The cryptolactones A1, A2, B1, and B2 isolated from a Cryptomyzus sp. aphid were synthesized via the Mukaiyama aldol reaction and olefin metathesis. Their antipodes and derivatives were also synthesized by the same strategy to investigate structure–activity relationships. These compounds exhibited cytotoxic activity against human promyelocytic leukemia HL-60 cells with IC50 values of 2.1–42 µM.

  通过 Mukaiyama 醛醇反应和烯烃复分解反应合成了从隐翅虫蚜虫中分离出来的隐内酯 A1、A2、B1 和 B2。为了研究结构-活性关系，我们还采用相同的策略合成了它们的对位化合物和衍生物。这些化合物对人类早幼粒细胞白血病 HL-60 细胞具有细胞毒性活性，IC50 值为 2.1-42 µM。
• 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.