5-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl-2-chloropyridine | 923924-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl-2-chloropyridine
• 英文别名: 2-chloro-5-[[(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl)thio]methyl]pyridine；2-[(6-Chloropyridin-3-yl)methylsulfanyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
• CAS: 923924-92-9
• 化学式: C₁₇H₁₆ClN₃O₄S
• 分子量: 393.851
• InChiKey: SYQOBNPDWLFKRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  565.8±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl-2-chloropyridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以48.5%的产率得到2-[(6-Chloropyridin-3-yl)methylsulfinyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety

  摘要：

  Selective oxidation of sulfides 7 or 8 to sulfoxides 9 or 10 is achieved by mCPBA. The structures of the compounds 9 or 10 are confirmed by elemental analysis, IR, and H-1 NMR. The bioassay results showed that title compound 10a possess high antifungal activities with EC50 values ranging from 19.91 to 63.97 mu g/mL. The mechanism of action of 10a against Sclerotinia sclerotiorum was studied. After treating with compound 10a at 100 mu g/mL for 12 h, the mycelial reducing sugar, D-GlcNAc, soluble protein and pyruvate content, chitinase activity showed declining tendency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.006
• 作为产物：
  描述：

  2-氯-5-氯甲基吡啶 、 5-(3,4,5-三甲氧基苯基)-[1,3,4]噁二唑-2-硫醇 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以60.1%的产率得到5-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl-2-chloropyridine
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents

  摘要：

  A series of new 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety were synthesized. Anti-proliferative assay results indicated that compounds 6o and 6u exhibited the most potent activity against gastric cancer cell SGC-7901, which was more potent than the positive control. Especially, compound 6o exhibited significant telomerase inhibitory activity (IC50 = 2.3 +/- 0.07 mu M), which was comparable to the positive control ethidium bromide. Docking simulation was performed to position compound 6o into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.051

文献信息

• Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents
  作者：Qing-Zhong Zheng、Xiao-Min Zhang、Ying Xu、Kui Cheng、Qing-Cai Jiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.09.051

  日期：2010.11.15

  A series of new 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety were synthesized. Anti-proliferative assay results indicated that compounds 6o and 6u exhibited the most potent activity against gastric cancer cell SGC-7901, which was more potent than the positive control. Especially, compound 6o exhibited significant telomerase inhibitory activity (IC50 = 2.3 +/- 0.07 mu M), which was comparable to the positive control ethidium bromide. Docking simulation was performed to position compound 6o into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety
  作者：Fang Liu、Xiao-Qiong Luo、Bao-An Song、Pinaki S. Bhadury、Song Yang、Lin-Hong Jin、Wei Xue、De-Yu Hu

  DOI：10.1016/j.bmc.2008.02.006

  日期：2008.4.1

  Selective oxidation of sulfides 7 or 8 to sulfoxides 9 or 10 is achieved by mCPBA. The structures of the compounds 9 or 10 are confirmed by elemental analysis, IR, and H-1 NMR. The bioassay results showed that title compound 10a possess high antifungal activities with EC50 values ranging from 19.91 to 63.97 mu g/mL. The mechanism of action of 10a against Sclerotinia sclerotiorum was studied. After treating with compound 10a at 100 mu g/mL for 12 h, the mycelial reducing sugar, D-GlcNAc, soluble protein and pyruvate content, chitinase activity showed declining tendency. (C) 2008 Elsevier Ltd. All rights reserved.