1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one | 1391500-64-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
• CAS: 1391500-64-3
• 化学式: C₂₀H₂₃ClO
• 分子量: 314.855
• InChiKey: CHYWHLZYMPOUNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one 在 氧气 作用下， 以 苯 为溶剂， 反应 0.67h， 以65%的产率得到8-[2-(o-chlorophenyl)ethenyl]-2,2,6-trimethyl-7,9,10-trioxatricyclo[6.2.2.0^1,6]dodec-11-ene
  参考文献：
  名称：

  β-Ionone derived apoptosis inducing endoperoxides; Discovery of potent leads for anticancer agents

  摘要：

  A series of endoperoxides (3a-j) were synthesized and evaluated for cytotoxic activity against four human cancer cell lines by using SRB dye assay. All the compounds displayed moderate to high cytotoxic effect against almost all investigational cancer cells. Particularly, compounds bearing electron withdrawing groups such as nitro substituted compound 3j (IC50 = 0.001 mu M) and fluor substituted compound 3i (IC50 = 0.003 mu M) showed comparatively more cytotoxic potential than standard drugs against lung cancer cell line (A549). All synthesized endoperoxides (3a-j) were further evaluated for their apoptotic potential through various parameters such as flow-cytometric analysis of nuclear DNA, flow-cytometric determination of mitochondrial membrane potential (Delta Psi(m)), spectrofluorimetric estimation of intracellular ROS level and caspase-3 & 9 assays in treated lung cancer cells (A549); results reveal that endoperoxides induce apoptosis in cancer cells via mitochondrial pathway. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.049
• 作为产物：
  描述：

  (EZ)-β-紫罗兰酮 、 2-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 以90%的产率得到1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis of β-ionone derived chalcones as potent antimicrobial agents

  摘要：

  A series of chalcones (3a-v) have been synthesized by condensation of beta-ionone (1) with a variety of aldehydes (2a-v). The synthesized compounds have been screened for their in vitro antimicrobial activity against five bacterial and five fungal strains, using disc diffusion assay. The evaluated compounds display a wide range of activities, from completely inactive to the highly active compounds. Some of the compounds are also active against methicillin resistant staphylococcus aureus (MRSA). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.084