2-{[2-oxo-2-(2-thienyl)ethyl]thio}-3-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one | 330449-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-{[2-oxo-2-(2-thienyl)ethyl]thio}-3-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-(2-Oxo-2-thiophen-2-ylethyl)sulfanyl-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 330449-43-9
• 化学式: C₂₂H₁₈N₂O₂S₃
• mdl: MFCD00818115
• 分子量: 438.595
• InChiKey: XGFQWEITNXPPPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  680.0±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2-(3-phenylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 在 caesium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 2-{[2-oxo-2-(2-thienyl)ethyl]thio}-3-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Development of thieno- and benzopyrimidinone inhibitors of the Hedgehog signaling pathway reveals PDE4-dependent and PDE4-independent mechanisms of action

  摘要：

  From a high content in vivo screen for modulators of developmental patterning in embryonic zebrafish, we previously identified eggmanone (EGM1, 3) as a Hedgehog (Hh) signaling inhibitor functioning downstream of Smoothened. Phenotypic optimization studies for in vitro probe development utilizing a Gli transcription-linked stable luciferase reporter cell line identified EGM1 analogs with improved potency and aqueous solubility. Mechanistic profiling of optimized analogs indicated two distinct scaffold clusters: PDE4 inhibitors able to inhibit downstream of Sufu, and PDE4-independent Hh inhibitors functioning between Smo and Sufu. Each class represents valuable in vitro probes for elucidating the complex mechanisms of Hh regulation. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.03.013

文献信息

• Compounds and methods for inhibition of hedgehog signaling and phosphodiesterase
  申请人：Vanderbilt University

  公开号：US10329304B2

  公开（公告）日：2019-06-25

  Compounds and compositions, and methods of use thereof, are provided and have utility in inhibiting hedgehog signaling and/or phosphodiesterase-4 activity.

  所提供的化合物和组合物及其使用方法可用于抑制刺猬信号和/或磷酸二酯酶-4 的活性。
• Small molecule BCL-2 functional converters as cancer therapeutics
  申请人：Oregon State University

  公开号：US11419843B2

  公开（公告）日：2022-08-23

  Methods for inducing growth inhibition or apoptosis of Bcl-2-expressing cells and treatments of Bcl-2 expressing cancers are provided. Additionally, assays for agents that can induce apoptosis of Bcl-2 expressing cells are disclosed.

  本研究提供了诱导表达 Bcl-2 的细胞生长抑制或凋亡以及治疗表达 Bcl-2 的癌症的方法。此外，还公开了可诱导 Bcl-2 表达细胞凋亡的制剂的检测方法。
• Compounds and Methods for Inhibition of Hedgehog Signaling and Phosphodiesterase
  申请人：Vanderbilt University

  公开号：US20170190717A1

  公开（公告）日：2017-07-06

  Compounds and compositions, and methods of use thereof, are provided and have utility in inhibiting hedgehog signaling and/or phosphodiesterase-4 activity.
• SMALL MOLECULE BCL-2 FUNCTIONAL CONVERTERS AS CANCER THERAPEUTICS
  申请人：Oregon State University

  公开号：US20190336469A1

  公开（公告）日：2019-11-07

  Methods for inducing growth inhibition or apoptosis of Bcl-2-expressing cells and treatments of Bcl-2 expressing cancers are provided. Additionally, assays for agents that can induce apoptosis of Bcl-2 expressing cells are disclosed.
• [EN] SMALL MOLECULE BCL-2 FUNCTIONAL CONVERTERS AS CANCER THERAPEUTICS<br/>[FR] CONVERTISSEURS FONCTIONNELS BCL-2 À PETITES MOLÉCULES UTILES EN TANT QU'AGENTS THÉRAPEUTIQUES CONTRE LE CANCER
  申请人：UNIV OREGON STATE

  公开号：WO2018102766A2

  公开（公告）日：2018-06-07

  Methods for inducing growth inhibition or apoptosis of Bcl-2-expressing cells and treatments of Bcl-2 expressing cancers are provided. Additionally, assays for agents that can induce apoptosis of Bcl-2 expressing cells are disclosed.