(4-乙氧基-3-甲氧基苄亚基)丙二腈 | 17229-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (4-乙氧基-3-甲氧基苄亚基)丙二腈
• 中文别名: (4-乙氧基-3-甲氧苯亚甲基)丙二腈
• 英文名称: 2-(3-methoxy-4-ethoxyphenyl)-1,1-dicyanoethylene
• 英文别名: 4-Ethoxy-3-methoxybenzyliden-malodinitril；4-Aethoxy-3-methoxybenzylidenmalononitril；Malononitrile, (4-ethoxy-3-methoxybenzylidene)-；2-[(4-ethoxy-3-methoxyphenyl)methylidene]propanedinitrile
• CAS: 17229-42-4
• 化学式: C₁₃H₁₂N₂O₂
• mdl: MFCD00174863
• 分子量: 228.25
• InChiKey: BHNNTPFLKFAPCD-UHFFFAOYSA-N

物化性质

• 沸点：
  388.6±37.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 (4-乙氧基-3-甲氧基苄亚基)丙二腈 以 乙醇 、 水 为溶剂， 反应 0.75h， 以88%的产率得到2-(3-methoxy-4-ethoxyphenyl)-1,1,2-tricyanoethane
  参考文献：
  名称：

  New Cyanoarylporphyrazines with High Sensitivity of Photophysical Parameters to Viscosity as Promising Agents for Photodynamic Therapy

  摘要：

  Photophysical properties and photodynamic activity for a series of cyanoarylporphyrazine pigments have been analyzed depending on the nature of the substituents and their position in the aromatic ring. Replacement of the fluorine atom in the para-position with the methoxy group leads to significant increase in the ratio of the dark and photoinduced cytotoxicities, i.e. potential therapeutic index of porphyrazine as photosensitizer in photodynamic cancer therapy.

  DOI：

  10.1134/s1070363220020140
• 作为产物：
  描述：

  4-乙氧基-3-甲氧基苯甲醛 、 丙二腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (4-乙氧基-3-甲氧基苄亚基)丙二腈
  参考文献：
  名称：

  合成，体外和计算机筛选2-氨基-4-芳基-6-（苯硫基）吡啶-3,5-二腈作为新型α-葡萄糖苷酶抑制剂。

  摘要：

  抑制α-葡萄糖苷酶对于治疗糖尿病（DM）至关重要。除许多有机支架外，以前已报道吡啶基化合物具有广泛的生物活性。本研究报告了一系列基于吡啶的合成类似物，通过体外，动力学和计算机模拟研究评估了其对α-葡萄糖苷酶抑制的潜力。为此目的，合成了2-氨基-4-芳基-6-（苯硫基）吡啶-3，5-二腈1-28，并进行了体外筛选。与标准阿卡波糖（IC50 = 750±10 µM）相比，包括1-3、7、9、11-14和16在内的几种类似物显示出许多潜在的抑制作用增加。有趣的是，化合物7（IC50 = 55.6±0.3 µM）的抑制强度是标准阿卡波糖的13倍。对最有效分子7的动力学研究揭示了竞争型抑制机制。在计算机上进行了研究以检查配体（化合物7）与α-葡糖苷酶的活性位点残基的结合模式。

  DOI：

  10.1016/j.bioorg.2020.103879

文献信息

• Synthesis, in vitro and in silico screening of 2-amino-4-aryl-6-(phenylthio) pyridine-3,5-dicarbonitriles as novel α-glucosidase inhibitors
  作者：Muhammad Ali、Khalid Mohammed Khan、Mohammad Mahdavi、Abdul Jabbar、Shahbaz Shamim、Uzma Salar、Muhammad Taha、Shahnaz Perveen、Bagher Larijani、Mohammad Ali Faramarzi

  DOI：10.1016/j.bioorg.2020.103879

  日期：2020.7

  study reports a series of pyridine based synthetic analogues for their α-glucosidase inhibitory potential assessed by in vitro, kinetics and in silico studies. For this purpose, 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles 1-28 were synthesized and subjected to in vitro screening. Several analogs, including 1-3, 7, 9, 11-14, and 16 showed many folds increased inhibitory potential in comparison

  抑制α-葡萄糖苷酶对于治疗糖尿病（DM）至关重要。除许多有机支架外，以前已报道吡啶基化合物具有广泛的生物活性。本研究报告了一系列基于吡啶的合成类似物，通过体外，动力学和计算机模拟研究评估了其对α-葡萄糖苷酶抑制的潜力。为此目的，合成了2-氨基-4-芳基-6-（苯硫基）吡啶-3，5-二腈1-28，并进行了体外筛选。与标准阿卡波糖（IC50 = 750±10 µM）相比，包括1-3、7、9、11-14和16在内的几种类似物显示出许多潜在的抑制作用增加。有趣的是，化合物7（IC50 = 55.6±0.3 µM）的抑制强度是标准阿卡波糖的13倍。对最有效分子7的动力学研究揭示了竞争型抑制机制。在计算机上进行了研究以检查配体（化合物7）与α-葡糖苷酶的活性位点残基的结合模式。
• Dihydropyrano [2,3-c] pyrazole: Novel in vitro inhibitors of yeast α-glucosidase
  作者：Hamdy Kashtoh、Munira Taj Muhammad、Jalaluddin J.A. Khan、Saima Rasheed、Ajmal Khan、Shahnaz Perveen、Kulsoom Javaid、Atia-tul-Wahab、Khalid Mohammed Khan、M. Iqbal Choudhary

  DOI：10.1016/j.bioorg.2016.01.008

  日期：2016.4

  Inhibition of alpha-glucosidase enzyme activity is a reliable approach towards controlling post-prandial hyperglycemia associated risk factors. During the current study, a series of dihydropyrano[ 2,3-c] pyrazoles (1-35) were synthesized and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 4, 22, 30, and 33 were found to be the potent inhibitors of the yeast alpha-glucosidase enzyme. Mechanistic studies on most potent compounds reveled that 1, 4, and 30 were non-competitive inhibitors (K-i = 9.75 +/- 0.07, 46 +/- 0.0001, and 69.16 +/- 0.01 mu M, respectively), compound 22 is a competitive inhibitor (K-i = 190 +/- 0.016 mu M), while 33 was an uncompetitive inhibitor (K-i = 45 +/- 0.0014 mu M) of the enzyme. Finally, the cytotoxicity of potent compounds (i.e. compounds 1, 4, 22, 30, and 33) was also evaluated against mouse fibroblast 3T3 cell line assay, and no toxicity was observed. This study identifies non-cytotoxic novel inhibitors of alpha-glucosidase enzyme for further investigation as anti-diabetic agents. (C) 2016 Elsevier Inc. All rights reserved.
• US7491486B2
  申请人：——

  公开号：US7491486B2

  公开（公告）日：2009-02-17
• New Cyanoarylporphyrazines with High Sensitivity of Photophysical Parameters to Viscosity as Promising Agents for Photodynamic Therapy
  作者：S. A. Lermontova、T. S. Lyubova、E. Yu. Ladilina、V. I. Plekhanov、I. V. Balalaeva、V. P. Boyarskii、L. G. Klapshina

  DOI：10.1134/s1070363220020140

  日期：2020.2

  Photophysical properties and photodynamic activity for a series of cyanoarylporphyrazine pigments have been analyzed depending on the nature of the substituents and their position in the aromatic ring. Replacement of the fluorine atom in the para-position with the methoxy group leads to significant increase in the ratio of the dark and photoinduced cytotoxicities, i.e. potential therapeutic index of porphyrazine as photosensitizer in photodynamic cancer therapy.