5-phenyl-2-propionylcyclohexane-1,3-dione | 1774-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-phenyl-2-propionylcyclohexane-1,3-dione
• 英文别名: 5-Phenyl-2-propionyl-cyclohexan-1.3-dion；5-Phenyl-2-propanoylcyclohexane-1,3-dione
• CAS: 1774-19-2
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: QRVCPVXKWBURJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡咯 、 5-phenyl-2-propionylcyclohexane-1,3-dione 以 甲醇 、 甲苯 为溶剂， 以58%的产率得到4-methyl-8-phenyl-1,2,3,3a,4,5,6,7,8,9-decahydropyrrolo[1,2-a]quinoline-5,6-dione
  参考文献：
  名称：

  Condensation of 2-Alkylcyclohexane-1,3-diones with Cyclic Azomethines

  摘要：

  Reaction of 2-acylcyclohexane-1,3-diones with 5- and 6-membered cyclic azomethines (3,4-dihydro-2H-pyrrole and 2,3,4,5-tetrahydropyridine) furnished derivatives of 2,3,3a,4,8,9-hexahydropyrrolo[1,2a]quinoline-5,6(1H,5aH)-dione and 3,4,4a,5,9,10-hexahydro-1H-pyrido[1,2-a]quinoline-6,7(2H,8H)-dione respectively. In reaction with 7-membered 3,4,5,6-tetrahydro-2H-azepine we failed to isolate polycyclic nitrogen-containing products.

  DOI：

  10.1023/b:rujo.0000045903.18108.84
• 作为产物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 丙酰氯 在 1H-1,2,4-三唑 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以51%的产率得到5-phenyl-2-propionylcyclohexane-1,3-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

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。
• FR2240915
  申请人：——

  公开号：——

  公开（公告）日：——
• Cyclohexane-1,3-dione derivatives, compositions containing them, processes for preparing them, and their use as herbicides and plant growth regulators
  申请人：ICI AUSTRALIA LIMITED

  公开号：EP0202042B1

  公开（公告）日：1990-05-09
• COMPOUNDS AND METHODS FOR ALTERING LIFESPAN OF EUKARYOTIC ORGANISMS
  申请人：University Of Rochester

  公开号：EP2501229A1

  公开（公告）日：2012-09-26
• Compounds and Methods for Altering Lifespan of Eukaryotic Organisms
  申请人：Goldfarb David S.

  公开号：US20130096175A1

  公开（公告）日：2013-04-18

  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.