5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carbaldehyde
• 英文别名: 5-(1,3-benzodioxol-5-yl)thiophene-2-carbaldehyde
• 化学式: C₁₂H₈O₃S
• 分子量: 232.26
• InChiKey: JTAZMPXFKZDHFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硫代乙内酰脲 、 5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carbaldehyde 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 15.0h， 以84%的产率得到5-((5-(benzo[d][1,3]dioxol-5-yl)thiophen-2-yl)methylene)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin

  摘要：

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).

  DOI：

  10.1021/jm401604x
• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 C₁₀H₇ClO₃ 在 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以73%的产率得到5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  β-卤代-α，β-不饱和醛与1,4-二噻吩-2,5-二醇的无金属级联反应：多环2-甲酰基噻吩的合成

  摘要：

  已经开发了一种无金属级联反应策略，用于从β-卤代-α，β-不饱和醛和1,4-二噻吩-2,5-二醇合成新型多环2-甲酰基噻吩。使用可回收的聚合物负载的有机碱进行反应过程。该合成方案用于合成几种新型多环噻吩，包括甾体D环退火的噻吩。我们的合成策略可提供高产率的噻吩，避免繁琐的后处理程序并最大程度地减少废物的形成。

  DOI：

  10.1039/c7ob01641g

文献信息

• [EN] SELECTIVE LIGANDS FOR TAU AGGREGATES<br/>[FR] LIGANDS SÉLECTIFS POUR AGRÉGATS TAU
  申请人：KARIN & STEN MORTSTEDT CBD SOLUTIONS AB

  公开号：WO2019025595A1

  公开（公告）日：2019-02-07

  The invention provides compounds of formula (I) and compositions comprising compounds of formula (I). The invention further provides uses of the compounds of formula (I) and compositions comprising compounds of formula (I), including the use of such compounds for the detection of tau deposits, and the use of such compounds and compositions as diagnostic agents in the diagnosis or monitoring of the progression of a disease or disorder such as Alzheimer's disease or corticobasal degeneration, or for the prevention or treatment of a disease or disorder such as Alzheimer's disease or corticobasal degeneration.

  该发明提供了公式（I）的化合物和包含公式（I）化合物的组合物。该发明还提供了公式（I）的化合物的用途和包含公式（I）化合物的组合物的用途，包括利用这些化合物检测tau沉积物，以及将这些化合物和组合物用作诊断剂，用于诊断或监测疾病或疾病进展的进展，例如阿尔茨海默病或皮质基底节变性，或用于预防或治疗疾病或疾病，例如阿尔茨海默病或皮质基底节变性。
• Distinct Heterocyclic Moieties Govern the Selectivity of Thiophene‐Vinylene‐Based Ligands towards Aβ or Tau Pathology in Alzheimer's Disease
  作者：Linnea Björk、Hamid Shirani、Yogesh Todarwal、Mathieu Linares、Ruben Vidal、Bernardino Ghetti、Patrick Norman、Therése Klingstedt、K. Peter R. Nilsson

  DOI：10.1002/ejoc.202300583

  日期：——

  variety of fluorescent thiophene-vinylene-based ligands was synthesized. Ligands with specific chemical composition displayed selectivity towards distinct protein aggregates in tissue sections with Alzheimer's disease pathology and distinct heterocyclic moieties governed the selectivity of the ligand towards Aβ or tau pathology. We foresee that these findings will aid in designing ligands towards disease-associated

  Tau be or not tau be.合成了多种基于荧光噻吩-乙烯基的配体。具有特定化学成分的配体对阿尔茨海默病病理学组织切片中不同的蛋白质聚集体表现出选择性，不同的杂环部分控制配体对 Aβ 或 tau 病理学的选择性。我们预计这些发现将有助于设计针对疾病相关蛋白质聚集体的配体。
• SELECTIVE LIGANDS FOR TAU AGGREGATES
  申请人：KARIN & STEN MORTSTEDT CBD SOLUTIONS AB

  公开号：US20200369659A1

  公开（公告）日：2020-11-26

  The invention provides compounds of formula (I) and compositions comprising compounds of formula (I). The invention further provides uses of the compounds of formula (I) and compositions comprising compounds of formula (I), including the use of such compounds for the detection of tau deposits, and the use of such compounds and compositions as diagnostic agents in the diagnosis or monitoring of the progression of a disease or disorder such as Alzheimer's disease or corticobasal degeneration, or for the prevention or treatment of a disease or disorder such as Alzheimer's disease or corticobasal degeneration.
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).
• A metal-free cascade reaction of β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diols: synthesis of polycyclic 2-formylthiophenes
  作者：Limi Goswami、Kashmiri Neog、Kumud Sharma、Pranjal Gogoi

  DOI：10.1039/c7ob01641g

  日期：——

  A metal-free cascade reaction strategy has been developed for the synthesis of novel polycyclic 2-formylthiophenes from β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diol. Recyclable polymer supported organic base was used to perform the reaction process. This synthetic protocol was applied to synthesize several novel polycyclic thiophenes including steroidal D-ring annelated thiophene. Our

  已经开发了一种无金属级联反应策略，用于从β-卤代-α，β-不饱和醛和1,4-二噻吩-2,5-二醇合成新型多环2-甲酰基噻吩。使用可回收的聚合物负载的有机碱进行反应过程。该合成方案用于合成几种新型多环噻吩，包括甾体D环退火的噻吩。我们的合成策略可提供高产率的噻吩，避免繁琐的后处理程序并最大程度地减少废物的形成。