1,1'-联(环己基)-3,3',5,5'-四酮 | 17844-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1'-联(环己基)-3,3',5,5'-四酮
• 英文名称: [1,1'-bi(cyclohexane)]-3,5-dione
• 英文别名: 5-Cyclohexyl-cyclohexandion-(1,3)；bicyclohexyl-3,5-dione；Bicyclohexyl-3,5-dion；1-Cyclohexyl-cyclohexandion-(3.5)；3.5-Dioxo-dicyclohexyl；5-Cyclohexylcyclohexane-1,3-dione
• CAS: 17844-66-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: LCYBPPUTWMUXAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  1,1'-联(环己基)-3,3',5,5'-四酮 在 1H-1,2,4-三唑 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 4-(1-((2-methoxyphenyl)amino)ethylidene)-[1,1'-bi(cyclohexane)]-3,5-dione
  参考文献：
  名称：

  Novel Colchicine-Site Binders with a Cyclohexanedione Scaffold Identified through a Ligand-Based Virtual Screening Approach

  摘要：

  Vascular disrupting agents (VDAs) constitute an innovative anticancer therapy that targets the tumor endothelium, leading to tumor necrosis. Our approach for the identification of new VDAs has relied on a ligand 3-D shape similarity virtual screening (VS) approach using the ROCS program as the VS tool and as query colchicine and TN-16, which both bind the alpha,beta-tubulin dimer. One of the hits identified, using TN-16 as query, has been explored by the synthesis of its structural analogues, leading to 2-(1-((2-methoxyphenyl)amino)ethylidene)-5-phenylcyclohexane-1,3-dione (compound 16c) with an IC50 = 0.09 +/- 0.01 mu M in HMEC-1 and BAEC, being 100-fold more potent than the initial hit. Compound 16c caused cell cycle arrest in the G2/M phase and interacted with the colchicine-binding site in tubulin, as confirmed by a competition assay with N,N'-ethylenebis(iodoacetamide) and by fluorescence spectroscopy. Moreover, 16c destroyed an established endothelial tubular network at 1 mu M and inhibited the migration and invasion of human breast carcinoma cells at 0.4 mu M. In conclusion, our approach has led to a new chemotype of promising antiproliferative compounds with antimitotic and potential VDA properties.

  DOI：

  10.1021/jm401939g
• 作为产物：
  描述：

  4-环己基-3-丁烯-2-酮 在 barium dihydroxide 、 sodium ethanolate 作用下， 生成 1,1'-联(环己基)-3,3',5,5'-四酮
  参考文献：
  名称：

  Kon, Journal of the Chemical Society, 1926, p. 1799

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS AND METHODS FOR ALTERING LIFESPAN OF EUKARYOTIC ORGANISMS<br/>[FR] COMPOSÉS ET PROCÉDÉS PERMETTANT DE MODIFIER LA DURÉE DE VIE D'ORGANISMES EUCARYOTES
  申请人：UNIV ROCHESTER

  公开号：WO2011062964A1

  公开（公告）日：2011-05-26

  Provided are compounds which generally have a triketone structure. Examples of the compounds include derivatives of 1,3-cyclohexanedione, such as: 1,3-cyclohexanedione, 2-propanoyl-5-cyclohexyl-; 1,3-cyclohexanedione, 2-propanoyl-5-[4-fluorophenyl]-; 1,3-cyclohexanedione, 2-acetyl-5-[thien-2-yl]-; 1,3-cyclohexanedione, 2-acetyl-5 -butyl-; and 1,3-cyclohexanedione, 2-propanoyl-5-[bicyclo[2.2.1]hept-2-en-5-yl]-. The compounds can be used to alter the lifespan of eukaryotic organisms and treat inflammation.

  提供的化合物通常具有三酮结构。这些化合物的示例包括1,3-环己二酮的衍生物，例如：1,3-环己二酮，2-丙酰基-5-环己基-；1,3-环己二酮，2-丙酰基-5-[4-氟苯基]-；1,3-环己二酮，2-乙酰基-5-[噻吩-2-基]-；1,3-环己二酮，2-乙酰基-5-丁基-；以及1,3-环己二酮，2-丙酰基-5-[双环[2.2.1]庚-2-烯-5-基]-。这些化合物可用于改变真核生物的寿命并用于治疗炎症。
• Substituted dihydropyridines and methods of use
  申请人：Hurt Ray Clarence

  公开号：US20070112015A1

  公开（公告）日：2007-05-17

  Compounds are provided that are modulators of the C5a receptor. The compounds are substituted dihydropyridines and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of C5a receptors.

  提供了调节C5a受体的化合物。这些化合物是取代二氢吡啶，并可用于制药组合物、治疗涉及C5a受体病理性激活的疾病和障碍的方法。
• Antimalarial drugs. 64. Synthesis and antimalarial properties of 1-imino derivatives of 7-chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and related structures
  作者：Stephen J. Kesten、Margaret J. Degnan、Jocelyn Hung、Dennis J. McNamara、Daniel F. Ortwine、Susan E. Uhlendorf、Leslie M. Werbel

  DOI：10.1021/jm00097a001

  日期：1992.9

  To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-[(alkylamino)alkylene]imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates. Among structural modifications prepared, including N-10-alkyl and C2-substituted analogs, removal of the C-9 oxygen, and introduction of an imino side chain at C-9, the imines of the N-10-H acridinediones were the most active compounds obtained. The [3-(NN-dimethylamino)propyl]imino derivative of 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.
• Nonsteroidal antiinflammatory agents. 1. 5-Alkoxy-3-biphenylylacetic acids and related compounds as new potential antiinflammatory agents
  作者：Yasumitsu Tamura、Yoshihiko Yoshimoto、Katsutoshi Kunimoto、Shinichi Tada、Toshio Tomita、Toshiyuki Wada、Eisuke Seto、Masao Murayama、Yoshihisa Shibata

  DOI：10.1021/jm00215a018

  日期：1977.5
• Baroni,E.E. et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 92 - 95
  作者：Baroni,E.E. et al.

  DOI：——

  日期：——