5-吡啶-4-基环己烷-1,3-二酮 | 75618-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-吡啶-4-基环己烷-1,3-二酮
• 英文名称: 5-(pyridin-4-yl)cyclohexane-1,3-dione
• 英文别名: 5-(4-pyridinyl)-1,3-cyclohexanedione；5-(4-pyridyl)cyclohexane-1,3-dione；5-Pyridin-4-ylcyclohexane-1,3-dione
• CAS: 75618-39-2
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: PLOQUILDFXDGMN-UHFFFAOYSA-N

物化性质

• 沸点：
  377.6±42.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-吡啶-4-基环己烷-1,3-二酮 在 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-3-pyridin-4-yl-1,3,4,10-tetrahydro-2H-acridin-9-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00097a001
• 作为产物：
  描述：

  (E)-4-(pyridin-4-yl)but-3-en-2-one 在 sodium hydroxide 、 硫酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-吡啶-4-基环己烷-1,3-二酮
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00097a001

文献信息

• Aminoguanidine hydrazone derivatives, process for producing the same and drugs thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06350749B1

  公开（公告）日：2002-02-26

  The present invention is to provide a compound of the formula: wherein the ring A is an optionally substituted 5- to 6-membered aromatic heterocyclic ring, the ring B an optionally substituted 5- to 6-membered aromatic homocyclic ring or an optionally substituted 5- to 6-membered aromatic heterocyclic ring, R1 is a hydrogen atom, a hydroxy group or a lower alkyl group, and n is 0 or 1, or a salt thereof, which is effective for the prevention or treatment of ischemic cardiac disease, etc., and which is useful as an agent for preventing or treating ischemic cardiac disease, etc. such as myocardial infarction, arrhythmia, etc.

  本发明提供了一种化合物的公式：其中环A是可选地取代的5至6成员芳香杂环，环B是可选地取代的5至6成员的芳香同环或可选地取代的5至6成员的芳香杂环，R1是氢原子，羟基或低烷基，n是0或1，或其盐，该盐对于预防或治疗缺血性心脏病等有效，并可作为预防或治疗缺血性心脏病等的药物，例如心肌梗死、心律失常等。
• Targeting the colchicine site in tubulin through cyclohexanedione derivatives
  作者：María-Dolores Canela、Oskía Bueno、Sam Noppen、Gonzalo Sáez Calvo、Juan Estévez Gallego、J. F. Díaz、María-José Camarasa、Sandra Liekens、María-Jesús Pérez-Pérez、Eva-María Priego

  DOI：10.1039/c5ra26807a

  日期：——

  Cyclohexanedione derivatives represent a new family of colchicine-site binders that were identified through a ligand-based virtual screening approach. Structural modifications have now been performed at both distal sites of our identified hit [2-(1-((2-methoxyphenyl)amino)ethylidene)-5-phenylcyclohexane-1,3-dione (4)] in order to improve tubulin binding affinity, anti-proliferative activity and/or

  环己二酮衍生物代表了一种新的秋水仙碱位结合剂家族，它们是通过基于配体的虚拟筛选方法鉴定出来的。现在已经在我们确定的命中[2-（1-（（（2-甲氧基苯基）氨基）亚乙基）-5-苯基环己烷-1,3-二酮（4）]的两个远端部位进行了结构修饰，以改善微管蛋白的结合亲和力，抗增殖活性和/或水溶性。获得的结果表明，根据对接研究，2-甲氧基苯基环（该片段更靠近αβ-微管蛋白界面）是允许结构变化以提高针对微管蛋白的K a值的化合物（如在化合物20a中，K a = 1.3×10 7M -1（类似于秋水仙碱）或提高水溶性，例如在化合物22c中，其可溶性比以前的命中4高10倍以上。
• Cyclohexane-1,3-Diones for Use in the Treatment of Amyotrophic Lateral Sclerosis
  申请人：Kirsch Donald R.

  公开号：US20120264765A1

  公开（公告）日：2012-10-18

  The present invention relates to the identification of provided cyclohexane-1,3-diones (CHD compounds) and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided CHD compounds.

  本发明涉及提供的环己烷-1,3-二酮（CHD化合物）的鉴定及其制备的药物组合物，用于治疗患有肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的受试者。本发明还提供了制备所述CHD化合物的方法。
• AMINOGUANIDINE HYDRAZONE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND DRUGS THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1057812A1

  公开（公告）日：2000-12-06

  The present invention is to provide a compound of the formula: wherein the ring A is an optionally substituted 5- to 6-membered aromatic heterocyclic ring, the ring B an optionally substituted 5- to 6-membered aromatic homocyclic ring or an optionally substituted 5- to 6-membered aromatic heterocyclic ring, R1 is a hydrogen atom, a hydroxy group or a lower alkyl group, and n is 0 or 1, or a salt thereof, which is effective for the prevention or treatment of ischemic cardiac disease, etc., and which is useful as preventing or treating agent for ischemic cardiac disease, etc. such as myocardial infarction, arrhythmia, etc.

  本发明旨在提供一种式化合物： 其中环A为任选取代的5-6元芳香杂环，环B为任选取代的5-6元芳香均环或任选取代的5-6元芳香杂环，R1为氢原子、羟基或低级烷基，n为0或1，或其盐，可有效预防或治疗缺血性心脏病等、可用作心肌梗塞、心律失常等缺血性心脏病的预防或治疗剂。
• PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLIC ENAMINONE DERIVATIVES
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1229019A1

  公开（公告）日：2002-08-07

  A process for the production of optically active cyclic enaminone derivatives characterized by aminating one of the carbonyl groups of a cyclic 1,3-diketone derivative having a symmetry plane to obtain an optically isomeric mixture of chiral cyclic enaminone derivatives and subjecting this mixture to optical resolution.

  一种生产光学活性环烯丙酮衍生物的工艺，其特征在于将具有对称平面的环 1，3-二酮衍生物的一个羰基胺化，得到手性环烯丙酮衍生物的光学异构体混合物，并对该混合物进行光学解析。