methyl 4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzoate | 1424272-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzoate
• 英文别名: methyl 4-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoate
• CAS: 1424272-40-1
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: KHOGYMBWOSYLEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzoate 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 N’-(2,4,5-trihydroxybenzylidene)-4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2yl)benzohydrazide
  参考文献：
  名称：

  Synthesis and molecular modelling studies of phenyl linked oxadiazole-phenylhydrazone hybrids as potent antileishmanial agents

  摘要：

  Molecular hybridization yielded phenyl linked oxadiazole-benzohydrazones hybrids 6-35 and were evaluated for their antileishmanial potentials. Compound 10, a 3,4-dihydroxy analog with IC50 value of 0.95 +/- 0.01 mu M, was found to be the most potent antileishmanial agent (7 times more active) than the standard drug pentamidine (IC50 = 7.02 +/- 0.09 mu M). The current series 6-35 conceded in the identification of thirteen (13) potent antileishmanial compounds with the IC50 values ranging between 0.95 +/- 0.01-78.6 +/- 1.78 mu M. Molecular docking analysis against pteridine reductase (PTR1) were also performed to probe the mode of action. Selectivity index showed that compounds with higher number of hydroxyl groups have low selectivity index. Theoretical stereochemical assignment was also done for certain derivatives by using density functional calculations. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.12.019
• 作为产物：
  描述：

  2-甲氧基亚苯基肼 在 吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 methyl 4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzoate
  参考文献：
  名称：

  含酚羟基和1,3,4-恶二唑基团的选择性和比色氟化物化学传感器

  摘要：

  两个新颖的阴离子传感器，4-（5-（5-（5-氯-2-羟基苯基）-1,3,4-恶二唑-2-基）苯甲酸甲酯（L1）和4-（5-（2-（2-羟基苯基）-）甲基据报道有1,3,4-恶二唑-2-基）苯甲酸酯（L2）。他们的光谱和色度特性的CH 2氯2 / CH 3 CN（1：2，V / V）与F溶液-感测，通过肉眼，紫外-可见和荧光测量的影响。具有共平面结构两者分子具有相邻的酚羟基和1,3,4-恶二唑单元，从而产生足够强的分子内氢键，阻碍最阴离子的缔合，但不是˚F -，具有酚羟基氢。他们显示从无色到在加入F的黄色，但不同的光的变化颜色的变化一样- 。

  DOI：

  10.1016/j.tetlet.2012.12.128

文献信息

• Synthesis of 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives and evaluation of their antiglycation potential
  作者：Muhammad Taha、Nor Hadiani Ismail、Waqas Jamil、Syahrul Imran、Fazal Rahim、Syed Muhammad Kashif、Mohd Zulkefeli

  DOI：10.1007/s00044-015-1476-8

  日期：2016.2

  In the search of potent antidiabetic drug, we synthesized 1-25 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives. First, we synthesized 2-methoxybenzohydrazide from methyl 2-methoxybenzoate which was treated with different arylaldehydes to afford 1-25 compounds. The synthesized compounds were evaluated for antiglycation activity. We found that 1-6 and 8 showed potent activity ranging from 160.2 to 290.17 A mu M better than standard drug rutin (IC50 = 295.09 +/- A 1.04 A mu M). All the synthesized compounds were characterized by different spectroscopy methods. These compounds can further be studied to develop lead antidiabetic compounds.