2-(dichloromethyl)-5-(3'-pyridinyl)-1,3,4-oxadiazole | 677347-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(dichloromethyl)-5-(3'-pyridinyl)-1,3,4-oxadiazole
• 英文别名: 3-[5-(Dichloromethyl)-1,3,4-oxadiazol-2-yl]pyridine；2-(dichloromethyl)-5-pyridin-3-yl-1,3,4-oxadiazole
• CAS: 677347-80-7
• 化学式: C₈H₅Cl₂N₃O
• 分子量: 230.053
• InChiKey: SRNHEGXWHXVZFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.81
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  二氯乙酸 、 3-吡啶甲酰肼 在 三氯氧磷 作用下， 反应 0.12h， 以85%的产率得到2-(dichloromethyl)-5-(3'-pyridinyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues

  摘要：

  Here the tyrosinase inhibition studies of library of 2,5-disubstituted-1,3,4-oxadiazoles have been reported and their structure-activity relationship (SAR) also have been discussed. The library of the oxadiazoles was synthesized under the microwave irradiation and was structures of these were characterized by different spectral techniques. From this study it could be concluded that for a better inhibition of tyrosinase, electronegative substitution is essential as most probably the active site of the enzyme contain some hydrophobic site and position is also very important for the inhibition purposes due to the conformational space. The electronegativity of the compounds is somewhat proportional to the inhibitory activity. The compound 3e (3 '-[5-(4 '-bromophenyl)-1,3,4-oxadiazol-2-yl]pyridine) exhibited most potent (IC50 = 2.18 mu M) inhibition against the enzyme tyrosinase which is more potent than the standard potent inhibitor L-mimosine IC50 = 3.68 mu M). This molecule can be the best candidate as a lead compound for further development of drug for the treatments of several skin disorders. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.012

文献信息

• 2,5-Disubstituted-1,3,4-oxadiazoles: thymidine phosphorylase inhibitors
  作者：Khalid Mohammed Khan、Mubeen Rani、Nida Ambreen、Muhammad Ali、Sajjad Hussain、Shahnaz Perveen、Muhammad Iqbal Choudhary

  DOI：10.1007/s00044-013-0588-2

  日期：2013.12

  A series of 2,5-disubstituted-1,3,4-oxadiazoles (1-16) were synthesized via microwave irradiation and screened against thymidine phosphorylase enzyme. Four members of the series have demonstrated thymidine phosphorylase inhibitory activities with IC50 values between 37 and 320 mu M. Pyridinyl-containing 1,3,4-oxadiazoles exhibited an enhanced inhibitory potential, while phenyl analogs did not show substantial inhibitory potential. Compound 9, a dipyridinyl residue having an IC50 value of 37 +/- A 0.76 mu M was found to be the most potent in the series superior to standard inhibitor 7-deazaxanthine (IC50 = 39.28 +/- A 0.76 mu M).