benzyl(2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydro-1H-inden-1-yl)sulfane

• 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: benzyl(2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydro-1H-inden-1-yl)sulfane
• 英文别名: (2R,3R)-1-benzylsulfanyl-2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydro-1H-indene
• 化学式: C₃₂H₃₂O₄S
• 分子量: 512.67
• InChiKey: ATDHBVOFEHZJPO-XNVRKLAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl(2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydro-1H-inden-1-yl)sulfane 在 硼烷四氢呋喃络合物 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.42h， 生成 C₃₂H₃₂O₅
  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
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸 在 indium(III) triflate 、 甲醇 、 sodium tetrahydroborate 、 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 43.0h， 生成 benzyl(2-(3,5-dimethoxyphenyl)-4,6-dimethoxy-3-phenyl-2,3-dihydro-1H-inden-1-yl)sulfane
  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

• Inhibitory effect of resveratrol dimerized derivatives on nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells
  作者：Chen Zhong、Xin-Hua Liu、Jun Chang、Jian-Ming Yu、Xun Sun

  DOI：10.1016/j.bmcl.2013.05.058

  日期：2013.8

  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.
• Synthesis, estrogenic activity, and anti-osteoporosis effects in ovariectomized rats of resveratrol oligomer derivatives
  作者：Xiao-Dong Hao、Jun Chang、Bo-Yin Qin、Chen Zhong、Zhi-Bo Chu、Jin Huang、Wen-Jiang Zhou、Xun Sun

  DOI：10.1016/j.ejmech.2015.07.042

  日期：2015.9

  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.