ethyl 2-(5-(4-chlorophenyl)-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetate | 449151-99-9

• 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-(5-(4-chlorophenyl)-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetate
• 英文别名: Ethyl 2-[5-(4-chlorophenyl)-4-oxothieno[2,3-d]pyrimidin-3-yl]acetate
• CAS: 449151-99-9
• 化学式: C₁₆H₁₃ClN₂O₃S
• 分子量: 348.81
• InChiKey: ZXPYEBBSUCHDNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(5-(4-chlorophenyl)-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetate 在 lithium hydroxide monohydrate 、 水 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-[2-(azetidin-1-yl)-2-oxoethyl]-5-(4-chlorophenyl)-3H,4H-thieno [2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  [EN] THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF
  [FR] MODULATEURS DES RÉCEPTEURS NMDA À BASE DE THIÉNOPYRIMIDINONE ET LEURS UTILISATIONS

  摘要：

  本文披露了部分杂环芳烃化合物以及在治疗神经精神障碍，如精神分裂症和重度抑郁症中的用途方法。提供了制备杂环芳烃化合物的药物组合物和方法。这些化合物被认为可以调节NMDA受体。

  公开号：

  WO2017100599A1
• 作为产物：
  描述：

  2-氨基-4-(4-氯苯基)-3-甲酸乙酯基噻吩 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 32.0h， 生成 ethyl 2-(5-(4-chlorophenyl)-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetate
  参考文献：
  名称：

  [EN] THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF
  [FR] MODULATEURS DES RÉCEPTEURS NMDA À BASE DE THIÉNOPYRIMIDINONE ET LEURS UTILISATIONS

  摘要：

  本文披露了部分杂环芳烃化合物以及在治疗神经精神障碍，如精神分裂症和重度抑郁症中的用途方法。提供了制备杂环芳烃化合物的药物组合物和方法。这些化合物被认为可以调节NMDA受体。

  公开号：

  WO2017100599A1

文献信息

• Thienopyrimidinone NMDA receptor modulators and uses thereof
  申请人：Cadent Therapeutics, Inc.

  公开号：US10973825B2

  公开（公告）日：2021-04-13

  Disclosed herein, in part, are methods of treating neurological disorders, e.g., schizophrenia and major depressive disorder, comprising administering an effective amount of a disclosed heterocyclic compound. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.

  本文部分公开了治疗神经系统疾病（如精神分裂症和重度抑郁症）的方法，包括施用有效量的已公开杂环化合物。提供了药物组合物和制造杂环化合物的方法。这些化合物可用于调节 NMDA 受体。
• Synthesis and anti-tumor activities of N′-benzylidene-2-(4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone derivatives
  作者：Jiangping Lou、Zhen Liu、Yan Li、Mi Zhou、Zhengxi Zhang、Shu Zheng、Renxiao Wang、Jian Li

  DOI：10.1016/j.bmcl.2011.09.061

  日期：2011.11

  A compound with a cyclic thienopyrimidine moiety and an aceto-hydrazone moiety in its chemical structure was discovered in a cell-based screening to have noticeable cytotoxicity on several tumor cell lines. A total of 38 derivatives of this compound were synthesized at five steps with high yields. These compounds were tested in standard MTT assays, and several compounds exhibited improved cytotoxic activities. The most potent compounds have IC50 values of 10-20 mu M on A549, HeLa, and MBA-MD-231 tumor cells. Flow cytometry analysis of several active compounds and subsequent examination of caspase activation indicate that they induce caspase-dependent apoptosis in tumor cells. In addition, these compounds do not have obvious effect on a normal cell line HEK-293T, demonstrating the desired selectivity against tumor cells. Results from a fluorescence polarization-based in vitro binding assay indicate that this class of compounds does not significantly interrupt the interactions between Mcl-1 and Bid. Their cytotoxicity is achieved presumably through other mechanisms. (C) 2011 Elsevier Ltd. All rights reserved.
• THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF
  申请人：Cadent Therapeutics, Inc.

  公开号：EP3386990A1

  公开（公告）日：2018-10-17
• THIENOPYRIMIDINONE NMDA RECEPTOR MODUCLATORS AND USES THEREOF
  申请人：CADENT THERAPEUTICS, INC.

  公开号：US20180360837A1

  公开（公告）日：2018-12-20

  Disclosed herein, in part, are methods of treating neurological disorders, e.g., schizophrenia and major depressive disorder, comprising administering an effective amount of a disclosed heterocyclic compound. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.
• [EN] THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE RÉCEPTEURS NMDA DE TYPE THIÉNOPYRIMIDINONE ET UTILISATIONS ASSOCIÉES
  申请人：LUC THERAPEUTICS

  公开号：WO2017100593A1

  公开（公告）日：2017-06-15

  Disclosed herein, in part, are methods of treating neurological disorders, e.g., schizophrenia and major depressive disorder, comprising administering an effective amount of a disclosed heterocyclic compound. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.