3t-[2,2']bithienyl-5-yl-acrylic acid | 3515-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3t-[2,2']bithienyl-5-yl-acrylic acid
• 英文别名: 3t-[2,2']Bithienyl-5-yl-acrylsaeure；(E)-3-(5-thiophen-2-ylthiophen-2-yl)prop-2-enoic acid
• CAS: 3515-26-2
• 化学式: C₁₁H₈O₂S₂
• 分子量: 236.315
• InChiKey: HWUXLEJHIBZOHB-GQCTYLIASA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  425.8±40.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 3t-[2,2']bithienyl-5-yl-acrylic acid 在 三乙胺 、 氯甲酸甲酯 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以68%的产率得到1-[(2E)-3-(2,2'-bithien-5-yl)prop-2-enoyl]piperidine
  参考文献：
  名称：

  Receptor- and Ligand-Based Study on Novel 2,2′-Bithienyl Derivatives as Non-Peptidic AANAT Inhibitors

  摘要：

  Arylalkylamine N-acetyl transferase (serotonin N-acetyl transferase, AANAT) is a critical enzyme in the light-mediated regulation of melatonin production and circadian rythm. With the objective of discovering new chemical entities with inhibitory potencies against AANAT, a medium-throughput screening campaign was performed on a chemolibrary. We found a class of molecules based on a 2,2'-bithienyl scaffold, and compound 1 emerged as a first hit. Herein, we describe our progress from hit discovery and to optimization of this new class of compounds. To complete the study, computational approaches were carried out: a docking study which provided insights into the plausible binding modes of these new AANAT inhibitors and a three-dimensional quantitative structure-activity relationship study that applied comparative molecular field analysis (CoMFA) methodology. Several CoMFA models were developed (variable alignments and options), and the best predictive one yields good statistical results (q(2) = 0.744, r(2) = 0.891, and s = 0.273). The resulting CoMFA contour reaps were used to illustrate the pharmacomodulations relevant to the biological activities in this series of analogs and to design new active inhibitors. This novel series of 2,2'-bithienyl derivatives gives new insights into the design of AANAT inhibitors.

  DOI：

  10.1021/ci9004805
• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 在 哌啶 、 吡啶 作用下， 生成 3t-[2,2']bithienyl-5-yl-acrylic acid
  参考文献：
  名称：

  Lescot et al., Journal of the Chemical Society, 1959, p. 3234,3235

  摘要：

  DOI：

文献信息

• Lescot et al., Journal of the Chemical Society, 1959, p. 3234,3235
  作者：Lescot et al.

  DOI：——

  日期：——
• Receptor- and Ligand-Based Study on Novel 2,2′-Bithienyl Derivatives as Non-Peptidic AANAT Inhibitors
  作者：Alban Lepailleur、Stéphane Lemaître、Xiao Feng、Jana Sopkova-de Oliveira Santos、Philippe Delagrange、Jean Boutin、Pierre Renard、Ronan Bureau、Sylvain Rault

  DOI：10.1021/ci9004805

  日期：2010.3.22

  Arylalkylamine N-acetyl transferase (serotonin N-acetyl transferase, AANAT) is a critical enzyme in the light-mediated regulation of melatonin production and circadian rythm. With the objective of discovering new chemical entities with inhibitory potencies against AANAT, a medium-throughput screening campaign was performed on a chemolibrary. We found a class of molecules based on a 2,2'-bithienyl scaffold, and compound 1 emerged as a first hit. Herein, we describe our progress from hit discovery and to optimization of this new class of compounds. To complete the study, computational approaches were carried out: a docking study which provided insights into the plausible binding modes of these new AANAT inhibitors and a three-dimensional quantitative structure-activity relationship study that applied comparative molecular field analysis (CoMFA) methodology. Several CoMFA models were developed (variable alignments and options), and the best predictive one yields good statistical results (q(2) = 0.744, r(2) = 0.891, and s = 0.273). The resulting CoMFA contour reaps were used to illustrate the pharmacomodulations relevant to the biological activities in this series of analogs and to design new active inhibitors. This novel series of 2,2'-bithienyl derivatives gives new insights into the design of AANAT inhibitors.