2-叔丁氧基羰基氨基-4,5,6,7-四氢-苯并b噻吩-3-羧酸甲酯 | 1313712-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-叔丁氧基羰基氨基-4,5,6,7-四氢-苯并b噻吩-3-羧酸甲酯
• 英文名称: methyl 2-((tert-butoxycarbonyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
• 英文别名: methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS: 1313712-54-7
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: YOXOEVFUXYRJIK-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-叔丁氧基羰基氨基-4,5,6,7-四氢-苯并b噻吩-3-羧酸甲酯 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以1.42 g的产率得到2-叔丁氧基羰基氨基-4,5,6,7-四氢-苯并b噻吩-3-羧酸
  参考文献：
  名称：

  1,4-Thienodiazepine-2,5-diones via MCR (I): Synthesis, Virtual Space and p53-Mdm2 Activity

  摘要：

  1,4‐Thienodiazepine‐2,5‐diones have been synthesized via the Ugi‐Deprotection‐Cyclization (UDC) approach starting from Gewald 2‐aminothiophenes in a convergent and versatile manner. The resulting scaffold is unprecedented, cyclic, and peptidomimetic with four points of diversity introduced from readily available starting materials. In addition to eighteen synthesized and characterized compounds, a virtual compound library was generated and evaluated for chemical space distribution and drug‐like properties. A small focused compound library of 1,4‐thienodiazepine‐2,5‐diones has been screened for the activity against p53‐Mdm2 interaction. Biological evaluations demonstrated that some compounds exhibited promising antagonistic activity.

  DOI：

  10.1111/j.1747-0285.2010.00989.x
• 作为产物：
  描述：

  环己酮 在 4-二甲氨基吡啶 、 sulfur 、 二乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-叔丁氧基羰基氨基-4,5,6,7-四氢-苯并b噻吩-3-羧酸甲酯
  参考文献：
  名称：

  1,4-Thienodiazepine-2,5-diones via MCR (I): Synthesis, Virtual Space and p53-Mdm2 Activity

  摘要：

  1,4‐Thienodiazepine‐2,5‐diones have been synthesized via the Ugi‐Deprotection‐Cyclization (UDC) approach starting from Gewald 2‐aminothiophenes in a convergent and versatile manner. The resulting scaffold is unprecedented, cyclic, and peptidomimetic with four points of diversity introduced from readily available starting materials. In addition to eighteen synthesized and characterized compounds, a virtual compound library was generated and evaluated for chemical space distribution and drug‐like properties. A small focused compound library of 1,4‐thienodiazepine‐2,5‐diones has been screened for the activity against p53‐Mdm2 interaction. Biological evaluations demonstrated that some compounds exhibited promising antagonistic activity.

  DOI：

  10.1111/j.1747-0285.2010.00989.x

文献信息

• Discovery of Small-Molecule Allosteric Inhibitors of <i>Pf</i>ATC as Antimalarials
  作者：Chao Wang、Bidong Zhang、Arne Krüger、Xiaochen Du、Lidia Visser、Alexander S S Dömling、Carsten Wrenger、Matthew R Groves

  DOI：10.1021/jacs.2c08128

  日期：2022.10.19

  The discovery and development of new drugs against malaria remain urgent. Aspartate transcarbamoylase (ATC) has been suggested to be a promising target for antimalarial drug development. Here, we describe a series of small-molecule inhibitors of P. falciparum ATC with low nanomolar binding affinities that selectively bind to a previously unreported allosteric pocket, thereby inhibiting ATC activation

  发现和开发抗疟疾的新药仍然很紧迫。天冬氨酸氨基甲酰转氨酶 (ATC) 已被认为是抗疟药物开发的有前途的目标。在这里，我们描述了一系列恶性疟原虫ATC 的小分子抑制剂，具有低纳摩尔结合亲和力，可选择性地结合以前未报告的变构口袋，从而抑制 ATC 激活。我们证明掩埋的变构口袋靠近传统的 ATC 活性位点，并且报告的化合物保持Pf的活性位点ATC 处于低底物亲和力/低活性构象。这些化合物以个位数微摩尔浓度抑制血液阶段培养物中的寄生虫生长，而对人类正常淋巴细胞的作用有限。据我们所知，该系列代表了第一个Pf ATC 特异性变构抑制剂。
• 1,4-Thienodiazepine-2,5-diones via MCR (II): Scaffold Hopping by Gewald and Ugi-Deprotection-Cyclization Strategy
  作者：Yijun Huang、Alexander Dömling

  DOI：10.1111/j.1747-0285.2010.00990.x

  日期：——

  A second scaffold of 1,4‐thienodiazepine‐2,5‐diones was discovered and is synthetically accessible from Gewald 2‐aminothiophenes via Ugi‐Deprotection‐Cyclization (UDC) strategy. This approach yielded hybrid peptidomimetic diazepine structures with six points of diversity introduced from readily available starting materials. A virtual compound library (N = 50 000) was generated and evaluated for chemical space distribution and drug‐like properties.
• 1,4-Thienodiazepine-2,5-diones via MCR (I): Synthesis, Virtual Space and p53-Mdm2 Activity
  作者：Yijun Huang、Siglinde Wolf、Michal Bista、Lidio Meireles、Carlos Camacho、Tad A. Holak、Alexander Dömling

  DOI：10.1111/j.1747-0285.2010.00989.x

  日期：——

  1,4‐Thienodiazepine‐2,5‐diones have been synthesized via the Ugi‐Deprotection‐Cyclization (UDC) approach starting from Gewald 2‐aminothiophenes in a convergent and versatile manner. The resulting scaffold is unprecedented, cyclic, and peptidomimetic with four points of diversity introduced from readily available starting materials. In addition to eighteen synthesized and characterized compounds, a virtual compound library was generated and evaluated for chemical space distribution and drug‐like properties. A small focused compound library of 1,4‐thienodiazepine‐2,5‐diones has been screened for the activity against p53‐Mdm2 interaction. Biological evaluations demonstrated that some compounds exhibited promising antagonistic activity.