(Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile | 1453269-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile
• 英文别名: (Z)-3-(1-benzothiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)prop-2-enenitrile
• CAS: 1453269-67-4
• 化学式: C₂₀H₁₇NO₃S
• 分子量: 351.426
• InChiKey: LJHKOZKMIRSYDV-RIYZIHGNSA-N

物化性质

• 沸点：
  520.5±50.0 °C(predicted)
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile 在 sodium azide 、 氯化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以87%的产率得到5-(benzo[b]thiophen-3-yl)-4-(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Preparation of 4,5 disubstituted-2H-1,2,3-triazoles from (Z)-2,3-diaryl substituted acrylonitriles

  摘要：

  2H-1,2,3-Triazoles (2) were synthesized by [3+2] cycloaddition of (Z)-2,3-diaryl substituted acrylonitriles (1) with sodium azide and ammonium chloride in DMF/water. This method represents a facile and efficient reaction procedure for the synthesis of 4,5-diary1-2H-1,2,3-triazoles in modest to good yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.045
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 3,4,5-三甲氧基苯乙腈 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile
  参考文献：
  名称：

  Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents

  摘要：

  我们合成了一个新的小分子库，其结构特征类似于考布他丁类似物，并评估了其对 60 种人类癌细胞株的抗癌活性。三种新型丙烯腈类似物（5、6 和 13）可显著降低几乎所有受检细胞系的细胞生长速度，其 GI50 值一般在 10-100 nM 之间。根据类似药物的结构特征，我们推测细胞毒性活性可能是由于与微管蛋白的相互作用。此外，这些化合物似乎还能克服细胞相关的P-糖蛋白（P-gp）介导的抗药性，因为它们在抑制OVCAR8和NCI/ADR-RES细胞生长方面效果相当。鉴于抗鸟嘌呤药物是治疗晚期前列腺癌最有效的药物之一，我们试图通过利用前列腺癌细胞系研究具有代表性的类似物 6 来验证 60 个细胞面板的结果，并探索这种类似物细胞毒性作用的分子机制。

  DOI：

  10.1039/c3md00130j

文献信息

• A novel and efficient tributyltin azide-mediated synthesis of 1H-tetrazolylstilbenes from cyanostilbenes
  作者：Narsimha Reddy Penthala、Shobanbabu Bommagani、Jaishankar Yadlapalli、Peter A. Crooks

  DOI：10.1016/j.tetlet.2016.03.040

  日期：2016.4

  A novel and efficient route was established for the synthesis of a series of (Z)-5-(2-(heteroaryl-2-yl) and (Z)-5-(3-(heteroaryl-3-yl)-1-(phenyl)vinyl)-1H-tetrazoles (3a–g and 6a–f, respectively) from cyanostilbene analogs containing benzo[b]thiophene, benzo[b]furan, and indole moieties utilizing tributyltin azide as a Lewis acid. This 1,3-dipolar [3+2]cycloaddition of azide to the cyano group of the

  建立了一种新颖且有效的路线来合成一系列（Z）-5-（2-（杂芳基-2-基）和（Z）-5-（3-（杂芳基-3-基）-1- （苯）乙烯基）-1 H-四唑（分别为3a - g和6a - f），它们来自氰基茂金属类似物，其中包含苯并[ b ]噻吩，苯并[ b ]呋喃和吲哚基团，使用三丁基叠氮化锡作为路易斯酸。叠氮化物的3，3-偶极[3 + 2]环加成到氰基茂金属前体分子的氰基上可提供相应四唑基茂金属类似物的良好产率，并且构成简单且成本有效的方法。
• [EN] METHODS OF PROTECTING AGAINST NEURODEGENERATION<br/>[FR] PROCÉDÉS DE PROTECTION CONTRE LA NEURODÉGÉNÉRESCENCE
  申请人：BIOVENTURES LLC

  公开号：WO2018144910A1

  公开（公告）日：2018-08-09

  The disclosure provides a method of preventing or reducing protein aggregates using combretastatin-A4 (CA4) or an analog thereof. The disclosure also provides methods of reducing the risk, delaying the onset, delaying or slowing the progression, or reversing the signs or symptoms of a neurodegenerative (or other age-progressive) disease using a combretastatin-A4 (CA4) or an analog thereof. The combretastatin-A4 (CA4) or an analog thereof may bind glial fibrillary acidic protein (GFAP). The combretastatin-A4 (CA4) or an analog thereof is described by compounds of Formula (I).
• Preparation of 4,5 disubstituted-2H-1,2,3-triazoles from (Z)-2,3-diaryl substituted acrylonitriles
  作者：Nikhil Reddy Madadi、Narsimha Reddy Penthala、Lin Song、Howard P. Hendrickson、Peter A. Crooks

  DOI：10.1016/j.tetlet.2014.05.045

  日期：2014.7

  2H-1,2,3-Triazoles (2) were synthesized by [3+2] cycloaddition of (Z)-2,3-diaryl substituted acrylonitriles (1) with sodium azide and ammonium chloride in DMF/water. This method represents a facile and efficient reaction procedure for the synthesis of 4,5-diary1-2H-1,2,3-triazoles in modest to good yields. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents
  作者：Narsimha Reddy Penthala、Vijayakumar N. Sonar、Jamie Horn、Markos Leggas、Jai Shankar K. B. Yadlapalli、Peter A. Crooks

  DOI：10.1039/c3md00130j

  日期：——

  A new library of small molecules with structural features resembling combretastatin analogs was synthesized and evaluated for anticancer activity against a panel of 60 human cancer cell lines. Three novel acrylonitrile analogs (5, 6 and 13) caused a significant reduction in cell growth in almost all the cell lines examined, with GI50 values generally in the range 10–100 nM. Based on the structural characteristics of similar drugs, we hypothesized that the cytotoxic activity was likely due to interaction with tubulin. Furthermore, these compounds appeared to overcome cell-associated P-glycoprotein (P-gp)-mediated resistance, since they were equipotent in inhibiting OVCAR8 and NCI/ADR-RES cell growth. Given that antitubulin drugs are among the most effective agents for the treatment of advanced prostate cancer we sought to validate the results from the 60 cell panel by studying the representative analog 6 utilizing prostate cancer cell lines, as well as exploring the molecular mechanism of the cytotoxic action of this analog.

  我们合成了一个新的小分子库，其结构特征类似于考布他丁类似物，并评估了其对 60 种人类癌细胞株的抗癌活性。三种新型丙烯腈类似物（5、6 和 13）可显著降低几乎所有受检细胞系的细胞生长速度，其 GI50 值一般在 10-100 nM 之间。根据类似药物的结构特征，我们推测细胞毒性活性可能是由于与微管蛋白的相互作用。此外，这些化合物似乎还能克服细胞相关的P-糖蛋白（P-gp）介导的抗药性，因为它们在抑制OVCAR8和NCI/ADR-RES细胞生长方面效果相当。鉴于抗鸟嘌呤药物是治疗晚期前列腺癌最有效的药物之一，我们试图通过利用前列腺癌细胞系研究具有代表性的类似物 6 来验证 60 个细胞面板的结果，并探索这种类似物细胞毒性作用的分子机制。