(2S,3S)-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3S)-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one
• 英文别名: trans-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one；(2R,3R)-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: XLIRSHIRYPKCAN-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one 在 indium(III) triflate 、 sodium tetrahydroborate 、 三溴化硼 、 碳酸氢钠 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 9.0h， 生成 3-(4-hydroxybenzyl)-2-(3,5-dihydroxyphenyl)-1-phenyl-1H-indene-5,7-diol
  参考文献：
  名称：

  Synthesis, estrogenic activity, and anti-osteoporosis effects in ovariectomized rats of resveratrol oligomer derivatives

  摘要：

  Three series of resveratrol oligomer derivatives were synthesized, including the indenone-type, indene-type and octahydropentalene-type derivatives, among which ten derivatives were novel compounds. Compounds 2, 14f, and 4d were confirmed as ER beta agonists by yeast two-hybrid assay, and compound 2 (isopaucifloral F) was further chosen to evaluate its anti-osteoporosis activity in vivo. Compared with the sham-operated and the positive control groups, isopaucifloral F (10 mu g/kg) showed a notable anti-osteoporosis effect in the ovariectomized (OVX) female rats based on a micro-CT analysis and the following measurements: bone mineral density, bone volume/tissue volume, trabecular thickness, trabecular separation/spacing, and the serum biochemical parameters. LD50 of isopaucifloral F was found to be greater than 5 mg/kg and its effective dose (ED) was found to be about 10 mu g/kg. Therefore, isopaucifloral F may be a promising lead compound for the treatment of postmenopausal osteoporosis. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.042
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸 在 萘 、 三氟化硼乙醚 、 potassium tert-butylate 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 41.0h， 生成 (2S,3S)-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydroinden-1-one
  参考文献：
  名称：

  Inhibitory effect of resveratrol dimerized derivatives on nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells

  摘要：

  Four types of resveratrol dimerized analogues were synthesized and evaluated in vitro on LPS-induced NO production in RAW 264.7 cells. The results showed that several compounds, especially those containing 1,2-diphenyl-2,3-dihydro-1H-indene core (type I), exhibited good inhibitory activities. Among 25 analogues, 12b showed a significant inhibitory activity (49% NO production at 10 mu M, IC50 = 3.38 mu M). Further study revealed that compound 12b could suppress LPS-induced iNOS expression, NO production, and IL-1 beta release in a concentration-dependently manner. The mechanism of action (MOA) involved for its anti-inflammatory responses was through signaling pathways of p38 MAPK and JNK1/2, but not ERK1/2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.058

文献信息

• Toward the Synthesis of Caraphenol C: Substituent Effect on the Nazarov ­Cyclization of 2-Arylchalcones
  作者：Xun Sun、Jun Zhu、Chen Zhong、Hong-Fu Lu、Guang-Yu Li

  DOI：10.1055/s-2008-1032065

  日期：2008.2

  A mild and versatile synthesis of cis-2,3-diarylindanones using a Nazarov cyclization strategy was reported. The substituent effect on the stereochemistry of the cyclization was discussed.

  报道了一种温和而多用途的合成cis-2,3-二芳基茚酮的方法，采用了Nazarov环化策略。讨论了取代基对环化立体化学的影响。
• Synthesis and biological evaluation of novel neuroprotective agents for paraquat-induced apoptosis in human neuronal SH-SY5Y cells
  作者：Chen Zhong、Xin-Hua Liu、Xiao-Dong Hao、Jun Chang、Xun Sun

  DOI：10.1016/j.ejmech.2012.12.037

  日期：2013.4

  Three types of resveratrol analogues were designed, synthesized and evaluated in vitro against paraquat-induced apoptosis in SH-SY5Y cells. The results showed that some compounds, especially those containing an indene core, exhibit good activities. Analogue 3'a showed a potent neuroprotective effect at a low concentration (10 mu M). Further investigation showed that compound 3'a could attenuate paraquat-induced nuclear morphological changes, significantly decrease paraquat-induced ROS (reactive oxygen species) generation in SH-SY5Y cells and elevate the expression of SOD (Superoxide Dismutase) and GPx (glutathione peroxidase) in a dose-dependent manner. Furthermore, analogue 3'a could decrease Bax protein levels in a concentration-dependent manner and increase Bcl-2 protein expression, which was accompanied by increasing chances of cell survival. (C) 2013 Elsevier Masson SAS. All rights reserved.