4-[5-cyano-2-(2,5-dimethylbenzylsulfanyl)-6-oxo-1,6-dihydro-pyrimidin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester | 1383539-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[5-cyano-2-(2,5-dimethylbenzylsulfanyl)-6-oxo-1,6-dihydro-pyrimidin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: 4-[5-Cyano-2-(2,5-Dimethylbenzylsulfanyl)-6-Oxo-1,6-Dihydro-Pyrimidin-4-Yl]-Piperidine-1-Carboxylic Acid Tert-Butyl Ester；tert-butyl 4-[5-cyano-2-[(2,5-dimethylphenyl)methylsulfanyl]-6-oxo-1H-pyrimidin-4-yl]piperidine-1-carboxylate
• CAS: 1383539-86-3
• 化学式: C₂₄H₃₀N₄O₃S
• 分子量: 454.593
• InChiKey: TVVPCYJZTNNWIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[5-cyano-2-(2,5-dimethylbenzylsulfanyl)-6-oxo-1,6-dihydro-pyrimidin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(2,5-dimethylbenzylsulfanyl)-6-oxo-4-piperidin-4-yl-1,6-dihydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  [EN] MODULATORS OF EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPACS)
  [FR] MODULATEURS DE PROTÉINES D'ÉCHANGE DIRECTEMENT ACTIVÉES PAR L'AMPC (EPAC)

  摘要：

  该发明的实施例涉及抑制EPAC蛋白活性的化合物以及使用这些化合物的方法。发明人已经开发了一种敏感且稳健的高通量筛选（HTS）测定方法，用于识别EPAC特异性抑制剂（Tsalkova等人（2012年）PLOS ONE 7(1)：e30441）。

  公开号：

  WO2013119931A1
• 作为产物：
  描述：

  1-叔丁氧羰基哌啶-4-甲醛 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 24.0h， 生成 4-[5-cyano-2-(2,5-dimethylbenzylsulfanyl)-6-oxo-1,6-dihydro-pyrimidin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  [EN] MODULATORS OF EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPACS)
  [FR] MODULATEURS DE PROTÉINES D'ÉCHANGE DIRECTEMENT ACTIVÉES PAR L'AMPC (EPAC)

  摘要：

  该发明的实施例涉及抑制EPAC蛋白活性的化合物以及使用这些化合物的方法。发明人已经开发了一种敏感且稳健的高通量筛选（HTS）测定方法，用于识别EPAC特异性抑制剂（Tsalkova等人（2012年）PLOS ONE 7(1)：e30441）。

  公开号：

  WO2013119931A1

文献信息

• MODULATORS OF EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPACS)
  申请人：The Board of Regents of the University of Texas System

  公开号：US20150110809A1

  公开（公告）日：2015-04-23

  Embodiments of the invention are directed to compounds that inhibit an activity of EP AC proteins and methods of using the same. The inventors have developed a sensitive and robust high throughput screening (HTS) assay for the purpose of identifying EPAC specific inhibitors (Tsalkova et al. (2012) PLOS ONE 7 (1):e30441).

  本发明的实施例涉及抑制EPAC蛋白活性的化合物及其使用方法。发明人开发了一种灵敏且强大的高通量筛选（HTS）检测方法，以识别EPAC特异性抑制剂（TSalkova等人（2012）PLOS ONE 7（1）：e30441）。
• 5-Cyano-6-oxo-1,6-dihydro-pyrimidines as potent antagonists targeting exchange proteins directly activated by cAMP
  作者：Haijun Chen、Tamara Tsalkova、Fang C. Mei、Yaohua Hu、Xiaodong Cheng、Jia Zhou

  DOI：10.1016/j.bmcl.2012.04.082

  日期：2012.6

  Exchange proteins directly activated by cAMP (Epac) are a family of guanine nucleotide exchange factors that regulate a wide variety of intracellular processes in response to second messenger cAMP. To explore the structural determinants for Epac antagonist properties of high throughput screening (HTS) hit ESI-08, pyrimidine 1, a series of 5-cyano-6-oxo-1,6-dihydro-pyrimidine analogues have been synthesized and evaluated for their activities for Epac inhibition. Structure-activity relationship (SAR) analysis led to the identification of three more potent Epac antagonists (6b, 6g, and 6h). These inhibitors may serve as valuable pharmacological probes for further elucidation of the physiological functions and mechanisms of Epac regulation. Our SAR results and molecular docking studies have also revealed that further optimization of the moieties at the C-6 position of pyrimidine scaffold may allow us to discover more potent Epac-specific antagonists. (C) 2012 Elsevier Ltd. All rights reserved.
• METHODS OF TREATING RICKETTSIA USING EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPACS) INHIBITORS
  申请人：Gong Bin

  公开号：US20140348853A1

  公开（公告）日：2014-11-27

  Embodiments of the invention are directed to compounds that inhibit an activity of EPAC proteins and methods of using the same.
• US9539256B2
  申请人：——

  公开号：US9539256B2

  公开（公告）日：2017-01-10
• [EN] ANTIMICROBIAL METHODS USING INHIBITORS OF EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPAC)<br/>[FR] PROCÉDÉS ANTIMICROBIENS UTILISANT DES INHIBITEURS DE PROTÉINES D'ÉCHANGE DIRECTEMENT ACTIVÉES PAR L'AMPC (EPAC)
  申请人：UNIV TEXAS

  公开号：WO2014123680A1

  公开（公告）日：2014-08-14

  Embodiments of the invention are directed to compositions and method for treating a viral infection. Embodiments of the invention are directed to medicine and health care. Certain embodiments are directed to methods of treating infectious disease. Additional embodiments are directed to the use of inhibitors of exchange proteins directly activated by cAMP (Epac) to treat viral infections.