2-({5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2-yl}sulfanyl)-1-(3-hydroxyphenyl)-1-ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-({5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2-yl}sulfanyl)-1-(3-hydroxyphenyl)-1-ethanone
• 英文别名: 1-(3-Hydroxyphenyl)-2-[[5-(4-phenylmethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethanone；1-(3-hydroxyphenyl)-2-[[5-(4-phenylmethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethanone
• 化学式: C₂₃H₁₈N₂O₄S
• 分子量: 418.473
• InChiKey: AONDABHAKPLTKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲酰肼 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.25h， 生成 2-({5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2-yl}sulfanyl)-1-(3-hydroxyphenyl)-1-ethanone
  参考文献：
  名称：

  Oxadiazoles and thiadiazoles: Novel α-glucosidase inhibitors

  摘要：

  Oxadiazoles and thiadiazoles 1-37 were synthesized and evaluated for the first time for their α-glucosidase inhibitory activities. As a result, fifteen of them 1, 4, 5, 7, 8, 13, 17, 23, 25, 30, 32, 33, 35, 36 and 37 were identified as potent inhibitors of the enzyme. Kinetic studies of the most active compounds (oxadiazoles 1, 23 and 25, and thiadiazoles 35 and 37) were carried out to determine their mode of inhibition and dissociation constants Ki. The most potent compound of the oxadiazole series (compound 23) was found to be a non-competitive inhibitor (Ki=4.36±0.017 μM), while most potent thiadiazole 35 was identified as a competitive inhibitor (Ki=6.0±0.059 μM). The selectivity and toxicity of these compounds were also studied by evaluating their potential against other enzymes, such as carbonic anhydrase-II and phosphodiesterase-I. Cytotoxicity was evaluated against rat fibroblast 3T3 cell line. Interestingly, these compounds were found to be inactive against other enzymes, exhibiting their selectivity towards α-glucosidase. Inhibition of α-glucosidase is an effective strategy for controlling post-prandial hyperglycemia in diabetic patients. α-Glucosidase inhibitors can also be used as anti-obesity and anti-viral drugs. Our study identifies two novel series of potent α-glucosidase inhibitors for further investigation.

  DOI：

  10.1016/j.bmc.2014.07.032

文献信息

• Oxadiazoles and thiadiazoles: Novel α-glucosidase inhibitors
  作者：Hamdy Kashtoh、Shafqat Hussain、Ajmal Khan、Syed Muhammad Saad、Jalaluddin A.J. Khan、Khalid Mohammed Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2014.07.032

  日期：2014.10

  Oxadiazoles and thiadiazoles 1-37 were synthesized and evaluated for the first time for their α-glucosidase inhibitory activities. As a result, fifteen of them 1, 4, 5, 7, 8, 13, 17, 23, 25, 30, 32, 33, 35, 36 and 37 were identified as potent inhibitors of the enzyme. Kinetic studies of the most active compounds (oxadiazoles 1, 23 and 25, and thiadiazoles 35 and 37) were carried out to determine their mode of inhibition and dissociation constants Ki. The most potent compound of the oxadiazole series (compound 23) was found to be a non-competitive inhibitor (Ki=4.36±0.017 μM), while most potent thiadiazole 35 was identified as a competitive inhibitor (Ki=6.0±0.059 μM). The selectivity and toxicity of these compounds were also studied by evaluating their potential against other enzymes, such as carbonic anhydrase-II and phosphodiesterase-I. Cytotoxicity was evaluated against rat fibroblast 3T3 cell line. Interestingly, these compounds were found to be inactive against other enzymes, exhibiting their selectivity towards α-glucosidase. Inhibition of α-glucosidase is an effective strategy for controlling post-prandial hyperglycemia in diabetic patients. α-Glucosidase inhibitors can also be used as anti-obesity and anti-viral drugs. Our study identifies two novel series of potent α-glucosidase inhibitors for further investigation.