ethyl 2-acetamido propionylacetate | 113185-81-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-acetamido propionylacetate
• 英文别名: Ethyl 2-acetamido-3-oxopentanoate；ethyl 2-acetamido-3-oxopentanoate
• CAS: 113185-81-2
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: RMIIKIBCBLLYIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methylpiperazin-1-ylsulfonyl)-2-propoxybenzimidamide 、 ethyl 2-acetamido propionylacetate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以42%的产率得到5-acetamido-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Monocyclic Pyrimidinones as Novel Inhibitors of PDE5

  摘要：

  Cyclic nucleotide phosphodiesterase type 5 (PDES) is a prime drug target for treating the diseases associated with a lower level of the cyclic guanosine monophosphate (cGMP), which is a specific substrate for PDE5 hydrolysis. Here we report a series of novel PDE5 inhibitors with the new scaffold of the monocyclic pyrimidin-4(3H)-one ring developed using the structure-based discovery strategy. In total, 37 derivatives of the pyrimidin-4(3H)-ones, were designed, synthesized, and evaluated for their inhibitory activities to PDES, resulting in 25 compounds with IC50 ranging from 1 to 100 nM and 11 compounds with IC50 ranging from 1 to 10 nM. Compound 5, 5,6-diethyl-2[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, the most potent compound, has an excellent IC50 (1.6 nM) in vitro and a good efficacy in a rat model of erection. It thus provides a potential candidate for the further development into a new drug targeting PDE5.

  DOI：

  10.1021/jm301159y
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 乙酸酐 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 生成 ethyl 2-acetamido propionylacetate
  参考文献：
  名称：

  Ti(iv)-catalyzed cascade synthesis of tetrahydrofuro[3,2-d]oxazole from arene-1,4-diones

  摘要：

  在室温下，利用TiCl₄/Et₃SiH的组合，对芳烃-1,4-二酮进行串联离子氢化、缩酮化和分子内环化反应，可轻松获得四氢呋喃[3,2-d]噁唑衍生物，并且收率良好。

  DOI：

  10.1039/c5ob00174a

文献信息

• CHEMICAL COMPOUNDS
  申请人：Chong PEK Yoke

  公开号：US20100216746A1

  公开（公告）日：2010-08-26

  The present invention relates to compounds that are a non-nucleoside reverse transcriptase inhibitors, and to processes for the preparation and use of the same. Specifically, the present invention includes methods of using such compounds in the treatment of human immunodeficiency virus infection.

  本发明涉及一种非核苷类逆转录酶抑制剂，以及制备和使用该类化合物的方法。具体而言，本发明包括使用这些化合物治疗人类免疫缺陷病毒感染的方法。
• PHENYL PYRIMIDONE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, PREPARATION METHODS AND USES THEREOF
  申请人：Topharman Shanghai Co., Ltd.

  公开号：EP2383262B1

  公开（公告）日：2016-07-06
• US8304419B2
  申请人：——

  公开号：US8304419B2

  公开（公告）日：2012-11-06
• US8871777B2
  申请人：——

  公开号：US8871777B2

  公开（公告）日：2014-10-28
• Design, Synthesis, and Pharmacological Evaluation of Monocyclic Pyrimidinones as Novel Inhibitors of PDE5
  作者：Guan Wang、Zheng Liu、Tiantian Chen、Zhen Wang、Huaiyu Yang、Mingyue Zheng、Jing Ren、Guanghui Tian、Xiaojun Yang、Li Li、Jianfeng Li、Jin Suo、Rongxia Zhang、Xiangrui Jiang、Nicholas Kenneth Terrett、Jingshan Shen、Yechun Xu、Hualiang Jiang

  DOI：10.1021/jm301159y

  日期：2012.12.13

  Cyclic nucleotide phosphodiesterase type 5 (PDES) is a prime drug target for treating the diseases associated with a lower level of the cyclic guanosine monophosphate (cGMP), which is a specific substrate for PDE5 hydrolysis. Here we report a series of novel PDE5 inhibitors with the new scaffold of the monocyclic pyrimidin-4(3H)-one ring developed using the structure-based discovery strategy. In total, 37 derivatives of the pyrimidin-4(3H)-ones, were designed, synthesized, and evaluated for their inhibitory activities to PDES, resulting in 25 compounds with IC50 ranging from 1 to 100 nM and 11 compounds with IC50 ranging from 1 to 10 nM. Compound 5, 5,6-diethyl-2[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, the most potent compound, has an excellent IC50 (1.6 nM) in vitro and a good efficacy in a rat model of erection. It thus provides a potential candidate for the further development into a new drug targeting PDE5.