4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one

• 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: 4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one
• 英文别名: 4-Benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-2,3-dihydroinden-1-one；4-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-2,3-dihydroinden-1-one
• 化学式: C₂₉H₂₄O₃
• 分子量: 420.508
• InChiKey: BBBVODRPSLPZKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one 在 sodium hydroxide 、 HPLC DIACEL OC column 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 2.0h， 生成 (R)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one
  参考文献：
  名称：

  Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

  摘要：

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00980-2
• 作为产物：
  描述：

  N,N-二乙基-4-溴苯甲酰胺 在 palladium on activated charcoal 、 Adam’s catalyst sodium hydroxide 、 四(三苯基膦)钯 、 氯化亚砜 、 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三溴化硼 、 四氯化钛 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 174.67h， 生成 4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one
  参考文献：
  名称：

  Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

  摘要：

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00980-2

文献信息

• Chiral deaza-coelenterazine analogs for probing a substrate-binding site in the Ca2+-binding photoprotein aequorin
  作者：Satoshi Inouye、Yuto Sumida、Yuri Tomabechi、Jumpei Taguchi、Mikako Shirouzu、Takamitsu Hosoya

  DOI：10.1371/journal.pone.0251743

  日期：——

  The Ca2+-binding photoprotein aequorin is a complex of apoAequorin (apoprotein) and (S)-2-peroxycoelenterazine. Aequorin can be regenerated by the incubation of apoAequorin with coelenterazine and molecular oxygen (O2). In this study, to investigate the molecular recognition of apoAequorin for coelenterazine using chemical probes, the chiral deaza-analogs of (S)- and (R)-deaza-CTZ (daCTZ) for coelenterazine

  Ca2+ 结合发光蛋白水母发光蛋白是载脂水母发光蛋白（脱辅基蛋白）和 (S)-2-过氧腔肠素的复合物。通过将脱辅基水母蛋白与腔肠素和分子氧 (O2) 一起孵育，可以再生水母发光蛋白。在本研究中，为了使用化学探针研究腔肠素的脱辅基水母蛋白的分子识别，腔肠素的(S)-和(R)-deaza-CTZ (daCTZ)以及(S)-2-和(S)-2-和(S)-2-和(采用改进方法，高效制备了2-过氧腔肠素R)-2-羟甲基-脱氮-CTZ（HM-daCTZ）。 (S)-daCTZ 和 (S)-HM-daCTZ 的手性脱氮类似物通过结合脱辅基水母发光蛋白分子中腔肠素的催化位点选择性抑制水母发光蛋白的再生步骤。确定了载脂蛋白水母蛋白与 (S)-daCTZ 和 (S)-HM-daCTZ 复合物的晶体结构，表明腔肠素中 C6-羟基苯基上的羟基部分和咪唑并吡嗪酮环上的羰基部分对于结合脱辅基水母发光蛋白分子通过氢键结合
• Design, Synthesis, and Evaluation of the Transition- State Inhibitors of Coelenterazine Bioluminescence:  Probing the Chiral Environment of Active Site
  作者：Hideshi Nakamura、Chun Wu、Satoshi Inouye、Akio Murai

  DOI：10.1021/ja005663v

  日期：2001.2.1
• Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase
  作者：Chun Wu、Hideshi Nakamura、Akio Murai、Satoshi Inouye

  DOI：10.1016/s0040-4020(01)00980-2

  日期：2001.11

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.