(2E,6E)-2,6-bis(3,4-dichlorobenzylidene)cyclohexanone | 59401-44-4

• 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: (2E,6E)-2,6-bis(3,4-dichlorobenzylidene)cyclohexanone
• 英文别名: (2E,6E)-2,6-bis[(3,4-dichlorophenyl)methylidene]cyclohexan-1-one
• CAS: 59401-44-4
• 化学式: C₂₀H₁₄Cl₄O
• 分子量: 412.143
• InChiKey: KGCULKJZSULNHU-VOMDNODZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2,6-bis(3,4-dichlorobenzylidene)cyclohexanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以32%的产率得到2,6-Bis-[1-(3,4-dichloro-phenyl)-meth-(E)-ylidene]-cyclohexanol
  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：

  环己酮 、 3,4-二氯苯甲醛 在 sodium hydroxide 作用下， 生成 (2E,6E)-2,6-bis(3,4-dichlorobenzylidene)cyclohexanone
  参考文献：
  名称：

  Mass Spectrometry of Some Substituted 2-Benzylidenecyclohexanones and 2,6-bis-Benzylidenecyclohexanones

  摘要：

  已确定了一系列一些取代的2-苄基亚甲基环己酮和一系列取代的2,6-双苄亚甲基环己酮的质谱在70 eV下。主要的碎裂途径包括分子内芳香取代反应，导致邻位取代基的丢失，形成稳定的苯并吡啶离子，从母离子中丢失一氧化碳和乙烯，以及从环己酮环的后续断裂中派生出的更多离子。通过比较从各种底物的光谱中确定的M - H/M和M - Cl/M比率，研究了参与芳香取代反应的结构和电子因素。

  DOI：

  10.1139/v73-220

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。
• Mass Spectrometry of Some Substituted 2-Benzylidenecyclohexanones and 2,6-bis-Benzylidenecyclohexanones
  作者：P. J. Smith、J. R. Dimmock、W. A. Turner

  DOI：10.1139/v73-220

  日期：1973.5.1

  The mass spectra of a series of some substituted 2-benzylidenecyclohexanones and a series of substituted 2,6-bis-benzylidenecyclohexanones have been determined at 70 eV. The major fragmentation pathways include an intramolecular aromatic substitution reaction leading to the loss of an ortho-substituent with the formation of a stable benzopyrylium ion, loss of carbon monoxide and ethylene from the parent ion and also further ions derived from subsequent cleavages of the cyclohexanone ring. The structural and electronic factors involved in the aromatic substitution reaction were examined by comparing the M – H/M and M – Cl/M ratios determined from the spectra of the various substrates.

  已确定了一系列一些取代的2-苄基亚甲基环己酮和一系列取代的2,6-双苄亚甲基环己酮的质谱在70 eV下。主要的碎裂途径包括分子内芳香取代反应，导致邻位取代基的丢失，形成稳定的苯并吡啶离子，从母离子中丢失一氧化碳和乙烯，以及从环己酮环的后续断裂中派生出的更多离子。通过比较从各种底物的光谱中确定的M - H/M和M - Cl/M比率，研究了参与芳香取代反应的结构和电子因素。
• Synthesis and Cytotoxic Evaluation of Some 6-Arylidene-2-(α-hydroxyamino-α-arylmethyl)cyclohexanone Oximes and Related Compounds
  作者：J.R. Dimmock、K.K. Sidhu、J.W. Quail、Z. Jia、M.J. Duffy、R.S. Reid、D.L. Kirkpatrick、L. Zhu、S.M. Fletcher

  DOI：10.1002/jps.2600811103

  日期：1992.11

  hydroxylamine hydrochloride and sodium acetate. Ten analogues of 5a, namely 5b-5k, were prepared and evaluated for cytotoxicity. Six of the 11 compounds in series 5, as well as 1, showed activity in the 240-950 microM range against murine mammary EMT6 cells. Series 5 was also examined for cytotoxicity in an in vitro screen conducted by the National Cancer Institute with approximately 54 cell lines, and

  2，6-双-（苯基亚甲基）环己酮（1）与4摩尔过量的羟胺盐酸盐和乙酸钠反应生成相应的肟2，生成2-（α-羟基氨基-α-苯基甲基）-6-苯基亚甲基环己酮一肟（5a），其结构由高分辨率质子核磁共振波谱推导，并通过X射线分析证实。最终由1与羟胺本身而不是由盐酸羟胺和乙酸钠的混合物制备化合物2。制备了10a的5a类似物，即5b-5k，并评估了细胞毒性。第5系列和11系列的11种化合物中有6种在240-950 microM范围内具有抗鼠乳腺EMT6细胞的活性。
• NHC-catalysed annulation of enals to tethered dienones: efficient synthesis of bicyclic dienes
  作者：Vijay Nair、Sreekumar Vellalath、Beneesh P. Babu、Vimal Varghese、Rony Rajan Paul、Eringathodi Suresh

  DOI：10.1039/c0ob00180e

  日期：——

  Homoenolates generated from α,β-unsaturated aldehydes using NHC catalysis underwent facile addition to dibenzylidene cyclohexanone to afford bicyclic cyclopentenes as single diastereomers.

  使用 NHC 催化法从 α、β-不饱和醛中生成的均烯醇酸盐与二亚苄基环己酮进行了简易加成，得到了单非对映异构体的双环环戊烯。