2,6-Bis[(4-tert-butylphenyl)methylidene]cyclohexan-1-one | 544666-27-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-Bis[(4-tert-butylphenyl)methylidene]cyclohexan-1-one
• CAS: 544666-27-5
• 化学式: C₂₈H₃₄O
• 分子量: 386.577
• InChiKey: YMZSPONKQSNRRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对叔丁基苯甲醛 、 环己酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,6-Bis[(4-tert-butylphenyl)methylidene]cyclohexan-1-one
  参考文献：
  名称：

  姜黄素的新型二芳基戊烷类似物对分泌性磷脂酶A2，环氧合酶，脂氧合酶和微粒体前列腺素E合酶-1的影响

  摘要：

  花生四烯酸及其代谢物由于其在炎症中的重要作用而引起了人们的关注。抑制花生四烯酸代谢中涉及的酶被认为是协同的抗炎作用。合成了一系列新型姜黄素二芳基戊烷类似物，并评估了它们对分泌性磷脂酶A 2，环加氧酶，大豆脂加氧酶以及微粒体前列腺素E合酶-1的抑制作用。之间的姜黄素类似物，化合物3，6，9，12，和17显示出分泌的磷脂酶A的强抑制2活性，以IC 50值范围从5.89到11.02  μ米。七姜黄素类似物1，3，6，7，9，11，和12环氧合酶-2的抑制表现出与IC 50值在46.11至94.86  μ米，这明显高于姜黄素的低。化合物3，6，7，12，和17对脂氧合酶的活性有很强的抑制作用。diarylpentanoid姜黄素类似物对微粒体前列腺素E合酶-1活性的初步筛选表明，4个diarylpentanoid姜黄素类似物5，6，7，和13表现出较高的抑制微粒体前列腺素E合酶-1活性的带IC 50范围从2

  DOI：

  10.1111/cbdd.12280

文献信息

• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.