3,5-Bis(3,4-dichlorobenzylidene)tetrahydro-4H-pyran-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Bis(3,4-dichlorobenzylidene)tetrahydro-4H-pyran-4-one
• 英文别名: (3E,5E)-3,5-bis[(3,4-dichlorophenyl)methylidene]oxan-4-one
• 化学式: C₁₉H₁₂Cl₄O₂
• 分子量: 414.115
• InChiKey: FTEZVWGWUVMYOA-ACFHMISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-Bis(3,4-dichlorobenzylidene)tetrahydro-4H-pyran-4-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以91%的产率得到3,5-Bis-[1-(3,4-dichloro-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone

  摘要：

  A number of 2,6-bisbenzylidenecyclohexane-1-one derivatives have been synthesized and tested as HIV-1 integrase (IN) inhibitors with the aim of obtaining compounds capable to elicit antiviral activity at non-cytotoxic concentrations in cell-based assays. 3,5-Bis(3,4,5-trihydroxybenzylidene)-4-oxocyclohexaneacetic acid (20d) resulted one of the most potent and selective derivatives in acutely infected MT-4 cells (EC50 and CC50 values of 2 and 40 muM, respectively). In enzyme assays with recombinant HIV-1 integrase (rIN), this compound proved able to inhibit both 3'-processing and disintegration with IC50 values of 0.2 and 0.5 muM, respectively. In order to develop a model capable to predict the anti HIV-IN activity and useful to design novel derivatives, we performed a comparative molecular field analysis (CoMFA) like 3-D-QSAR. In our model the ligands were described quantitatively in the GRID program, and the model was optimized by selecting only the most informative variables in the GOLPE program. We found the predictive ability of the model to increase significantly when the number of variables was reduced from 20,925 to 1327. A Q(2) of 0.73 was obtained with the final model, confirming the predictive ability of the model. By studying the PLS coefficients in informative 3-D contour plots, ideas for the synthesis of new compounds could be generated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.005
• 作为产物：
  描述：

  四氢吡喃酮 、 3,4-二氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以51%的产率得到3,5-Bis(3,4-dichlorobenzylidene)tetrahydro-4H-pyran-4-one
  参考文献：
  名称：

  2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone

  摘要：

  A number of 2,6-bisbenzylidenecyclohexane-1-one derivatives have been synthesized and tested as HIV-1 integrase (IN) inhibitors with the aim of obtaining compounds capable to elicit antiviral activity at non-cytotoxic concentrations in cell-based assays. 3,5-Bis(3,4,5-trihydroxybenzylidene)-4-oxocyclohexaneacetic acid (20d) resulted one of the most potent and selective derivatives in acutely infected MT-4 cells (EC50 and CC50 values of 2 and 40 muM, respectively). In enzyme assays with recombinant HIV-1 integrase (rIN), this compound proved able to inhibit both 3'-processing and disintegration with IC50 values of 0.2 and 0.5 muM, respectively. In order to develop a model capable to predict the anti HIV-IN activity and useful to design novel derivatives, we performed a comparative molecular field analysis (CoMFA) like 3-D-QSAR. In our model the ligands were described quantitatively in the GRID program, and the model was optimized by selecting only the most informative variables in the GOLPE program. We found the predictive ability of the model to increase significantly when the number of variables was reduced from 20,925 to 1327. A Q(2) of 0.73 was obtained with the final model, confirming the predictive ability of the model. By studying the PLS coefficients in informative 3-D contour plots, ideas for the synthesis of new compounds could be generated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.005

文献信息

• Small Molecule Stimulators of Steroid Receptor Coactivator-3 and Methods of Their Use as Cardioprotective and/or Vascular Regenerative Agents
  申请人：Baylor College of Medicine

  公开号：US20200071300A1

  公开（公告）日：2020-03-05

  Small molecule stimulators of steroid receptor coactivator-3 (SRC-3) and methods of their use as cardioprotective agents are provided. The small molecule stimulators are useful for promoting cardiac protection and repair and vascular regeneration after myocardial infarction. The compounds are also useful in preventing cardiac hypertrophy and collagen deposition and improving cardiac post-infarction function.

  提供了类固醇受体共激活因子-3（SRC-3）的小分子激活剂以及它们作为心脏保护剂的使用方法。这些小分子激活剂有助于促进心脏保护和修复，以及在心肌梗死后促进血管再生。这些化合物还可用于预防心肌肥大和胶原沉积，改善心肌梗死后的心脏功能。
• [EN] SMALL MOLECULE STIMULATORS OF STEROID RECEPTOR COACTIVATOR PROTEINS AND THEIR USE IN THE TREATMENT OF CANCER<br/>[FR] STIMULATEURS À PETITES MOLÉCULES DES PROTÉINES CO-ACTIVATRICES DES RÉCEPTEURS DE STÉROÏDES ET MÉTHODES POUR LES UTILISER
  申请人：BAYLOR COLLEGE MEDICINE

  公开号：WO2016109470A1

  公开（公告）日：2016-07-07

  Small molecule stimulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing cancer. Also provided are methods for stimulating SRC family proteins in a cell.

  提供了激活类固醇受体共激活蛋白（SRC）家族蛋白的小分子刺激剂，以及它们在治疗或预防癌症中的使用方法。还提供了在细胞中刺激SRC家族蛋白的方法。
• Small molecule stimulators of steroid receptor coactivator-3 and methods of their use as cardioprotective and/or vascular regenerative agents
  申请人：Baylor College of Medicine

  公开号：US10875841B2

  公开（公告）日：2020-12-29

  Small molecule stimulators of steroid receptor coactivator-3 (SRC-3) and methods of their use as cardioprotective agents are provided. The small molecule stimulators are useful for promoting cardiac protection and repair and vascular regeneration after myocardial infarction. The compounds are also useful in preventing cardiac hypertrophy and collagen deposition and improving cardiac post-infarction function.

  本研究提供了类固醇受体辅激活剂-3（SRC-3）的小分子刺激剂及其用作心脏保护剂的方法。 这些小分子刺激剂有助于促进心肌梗塞后的心脏保护和修复以及血管再生。 这些化合物还能防止心脏肥大和胶原沉积，改善心肌梗塞后的功能。
• Small molecule stimulators of steroid receptor coactivator proteins and their use in the treatment of cancer
  申请人：BAYLOR COLLEGE OF MEDICINE

  公开号：US11312676B2

  公开（公告）日：2022-04-26

  Small molecule stimulators of steroid receptor coactivator (SRC) family proteins are provided, as well as methods for their use in treating or preventing cancer. Also provided are methods for stimulating SRC family proteins in a cell.

  本研究提供了类固醇受体辅激活剂（SRC）家族蛋白的小分子刺激剂，以及将其用于治疗或预防癌症的方法。还提供了刺激细胞中 SRC 家族蛋白的方法。
• SMALL MOLECULE STIMULATORS OF STEROID RECEPTOR COACTIVATOR-3 AND METHODS OF THEIR USE AS CARDIOPROTECTIVE AND/OR VASCULAR REGENERATIVE AGENTS
  申请人：BAYLOR COLLEGE OF MEDICINE

  公开号：US20210115017A1

  公开（公告）日：2021-04-22

  Small molecule stimulators of steroid receptor coactivator-3 (SRC-3) and methods of their use as cardioprotective agents are provided. The small molecule stimulators are useful for promoting cardiac protection and repair and vascular regeneration after myocardial infarction. The compounds are also useful in preventing cardiac hypertrophy and collagen deposition and improving cardiac post-infarction function.