N-(3-chlorophenethyl)-N'-cyclopentylpyrimidine-2,4,6-trione | 1391385-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(3-chlorophenethyl)-N'-cyclopentylpyrimidine-2,4,6-trione
• 英文别名: 1-(3-chlorophenethyl)-3-cyclopentylpyrimidine-2,4,6[1H,3H,5H]-trione；N-(3-chlorophenethyl)-N'-cyclopentyl-pyrimidine-2,4,6-(1H,3H,5H)-trione；CaV1.3 antagonist-1；1-[2-(3-chlorophenyl)ethyl]-3-cyclopentyl-1,3-diazinane-2,4,6-trione
• CAS: 1391385-57-1
• 化学式: C₁₇H₁₉ClN₂O₃
• 分子量: 334.802
• InChiKey: AJKSBVCOTKODMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁氧羰酰基6-氨基己酸 、 N-(3-chlorophenethyl)-N'-cyclopentylpyrimidine-2,4,6-trione 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a fluorescent chemical probe for imaging of L-type voltage-gated calcium channels

  摘要：

  Herein, we report the synthesis of a chemical probe for real-time visualization of L-type voltage-gated calcium channels (LTCCs) using fluorescence microscopy. The probe, FluoBar2, is based on a barbiturate ligand selective for LTCCs. FluoBar2 contains the organic fluorophore 5-carboxyfluorescein and was synthesized in seven total steps with a 22% overall yield.

  DOI：

  10.1139/cjc-2023-0149
• 作为产物：
  描述：

  环戊基异氰酸酯 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-(3-chlorophenethyl)-N'-cyclopentylpyrimidine-2,4,6-trione
  参考文献：
  名称：

  Synthesis of a fluorescent chemical probe for imaging of L-type voltage-gated calcium channels

  摘要：

  Herein, we report the synthesis of a chemical probe for real-time visualization of L-type voltage-gated calcium channels (LTCCs) using fluorescence microscopy. The probe, FluoBar2, is based on a barbiturate ligand selective for LTCCs. FluoBar2 contains the organic fluorophore 5-carboxyfluorescein and was synthesized in seven total steps with a 22% overall yield.

  DOI：

  10.1139/cjc-2023-0149

文献信息

• Structure–Activity Relationship of N,N′-Disubstituted Pyrimidinetriones as Ca_V1.3 Calcium Channel-Selective Antagonists for Parkinson’s Disease
  作者：Soosung Kang、Garry Cooper、Sara Fernandez Dunne、Chi-Hao Luan、D. James Surmeier、Richard B. Silverman

  DOI：10.1021/jm4005048

  日期：2013.6.13

  CaV1.3 L-type calcium channels (LTCCs) have been a potential target for Parkinson’s disease since calcium ion influx through the channel was implicated in the generation of mitochondrial oxidative stress, causing cell death in the dopaminergic neurons. Selective inhibition of CaV1.3 over other LTCC isoforms, especially CaV1.2, is critical to minimize potential side effects. We recently identified pyrimidinetriones

  Ca V 1.3 L 型钙通道 (LTCC) 已成为帕金森病的潜在靶标，因为钙离子通过该通道流入与线粒体氧化应激的产生有关，从而导致多巴胺能神经元中的细胞死亡。选择性抑制 Ca V 1.3 对其他 LTCC 同种型，尤其是 Ca V 1.2，对于最大限度地减少潜在副作用至关重要。我们最近将嘧啶三酮 (PYT) 鉴定为 Ca V 1.3 选择性支架；在这里，我们报告了 PYTs 与 Ca V 1.3 和 Ca V 1.2 LTCC的构效关系。通过改变 PYT 的环戊基和芳烷基上的取代基，SAR 研究允许表征 CaV 1.3 和 Ca V 1.2 LTCC 结合位点。SAR 还确定了四个重要的部分，它们保留了选择性或增强了结合亲和力。我们的研究代表了 Ca V 1.3 和 Ca V 1.2 LTCC中 PYT 的 SAR 的显着增强，并突出了该系列化合物用于药物开发的先导优化和多样化方面的一些进展。
• [EN] SELECTIVE CALCIUM CHANNEL ANTAGONISTS<br/>[FR] ANTAGONISTES SÉLECTIFS DES CANAUX CALCIQUES
  申请人：UNIV NORTHWESTERN

  公开号：WO2012100073A1

  公开（公告）日：2012-07-26

  The present invention relates to compositions and methods for the treatment and/or prevention of neurodegenerative disorders, e.g., Parkinson's disease (PD). In particular, the present invention provides compositions comprising selective antagonists of calcium ion channels (e.g., cav 1.3 -type ion channels), and methods of use thereof to treat or prevent neurodegenerative disorders.

  本发明涉及用于治疗和/或预防神经退行性疾病，例如帕金森病（PD）的组合物和方法。具体地，本发明提供包含钙离子通道的选择性拮抗剂（例如，cav 1.3型离子通道）的组合物，以及利用这些方法来治疗或预防神经退行性疾病。
• Selective calcium channel antagonists
  申请人：Northwestern University

  公开号：US10105366B2

  公开（公告）日：2018-10-23

  The present invention relates to compositions and methods for the treatment and/or prevention of neurodegenerative disorders, e.g., Parkinson's disease (PD). In particular, the present invention provides compositions comprising selective antagonists of calcium ion channels (e.g., cav1.3-type ion channels), and methods of use thereof to treat or prevent neurodegenerative disorders.

  本发明涉及治疗和/或预防神经退行性疾病（如帕金森病（PD））的组合物和方法。特别是，本发明提供了包含钙离子通道（如cav1.3型离子通道）选择性拮抗剂的组合物及其用于治疗或预防神经退行性疾病的方法。
• SELECTIVE CALCIUM CHANNEL ANTAGONISTS
  申请人：Surmeier, JR. Dalton J.

  公开号：US20120196883A1

  公开（公告）日：2012-08-02

  The present invention relates to compositions and methods for the treatment and/or prevention of neurodegenerative disorders, e.g., Parkinson's disease (PD). In particular, the present invention provides compositions comprising selective antagonists of calcium ion channels (e.g., cav1.3-type ion channels), and methods of use thereof to treat or prevent neurodegenerative disorders.
• US9428467B2
  申请人：——

  公开号：US9428467B2

  公开（公告）日：2016-08-30