diethyl 2-benzyl-2-octylmalonate | 15326-97-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-benzyl-2-octylmalonate
• 英文别名: benzyl-octyl-malonic acid diethyl ester；Benzyl-octyl-malonsaeure-diaethylester；diethyl 2-benzyl-2-n-octylmalonate；Diethyl 2-benzyl-2-octylpropanedioate
• CAS: 15326-97-3
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: BFRRRLGYZKQJRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-benzyl-2-octylmalonate 在 sodium hydroxide 作用下， 生成 (RS)-2-benzyldecanoic acid
  参考文献：
  名称：

  Ukita et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 289,291

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸二乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 41.75h， 生成 diethyl 2-benzyl-2-octylmalonate
  参考文献：
  名称：

  Validating the 1,2-Difluoro Motif As a Hybrid Bioisostere of CF₃ and Et Using Matrix Metalloproteinases As Structural Probes

  摘要：

  Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by advances in structural biology. Herein, we harness MMPs 2, 8, 9, and 13 to validate the vicinal difluoro motif as a hybrid bioisostere of CF3 and Et (BITE) in a series of modified barbiturate inhibitors. Crystallographic analyses of representative structures reveal conformations of the vicinal difluoro motif that manifest stabilizing hyperconjugative interactions consistent with the stereoelectronic gauche effect. Detailed docking studies of a potent difluorinated probe with MMP-9 are also disclosed and indicate that the structural basis of inhibition is a consequence of the anisotropic nature of the motif. Significant selectivity of MMP 13 versus MMP-2 can be achieved by subtle chain contraction in a BITE-modified inhibitor.

  DOI：

  10.1021/acs.jmedchem.0c00648

文献信息

• Mesomorphic compound, liquid crystal composition, liquid crystal device, display apparatus and display method
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP0546338B1

  公开（公告）日：1998-02-04
• Naik et al., Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1950, vol. 19/A, p. 54,56
  作者：Naik et al.

  DOI：——

  日期：——
• US5385692A
  申请人：——

  公开号：US5385692A

  公开（公告）日：1995-01-31
• Validating the 1,2-Difluoro Motif As a Hybrid Bioisostere of CF₃ and Et Using Matrix Metalloproteinases As Structural Probes
  作者：Nathalie Erdeljac、Christian Thiehoff、Ravindra P. Jumde、Constantin G. Daniliuc、Sandra Höppner、Andreas Faust、Anna K. H. Hirsch、Ryan Gilmour

  DOI：10.1021/acs.jmedchem.0c00648

  日期：2020.6.11

  Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by advances in structural biology. Herein, we harness MMPs 2, 8, 9, and 13 to validate the vicinal difluoro motif as a hybrid bioisostere of CF3 and Et (BITE) in a series of modified barbiturate inhibitors. Crystallographic analyses of representative structures reveal conformations of the vicinal difluoro motif that manifest stabilizing hyperconjugative interactions consistent with the stereoelectronic gauche effect. Detailed docking studies of a potent difluorinated probe with MMP-9 are also disclosed and indicate that the structural basis of inhibition is a consequence of the anisotropic nature of the motif. Significant selectivity of MMP 13 versus MMP-2 can be achieved by subtle chain contraction in a BITE-modified inhibitor.
• Ukita et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 289,291
  作者：Ukita et al.

  DOI：——

  日期：——