5-(chloromethyl)-7-(2-chlorophenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(chloromethyl)-7-(2-chlorophenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide
• 英文别名: 5-(Chloromethyl)-7-(2-chlorophenyl)-3,4-dihydrooxathiino[6,5-c]pyrazole 2,2-dioxide；5-(chloromethyl)-7-(2-chlorophenyl)-3,4-dihydrooxathiino[6,5-c]pyrazole 2,2-dioxide
• 化学式: C₁₂H₁₀Cl₂N₂O₃S
• 分子量: 333.195
• InChiKey: ZXXPHLTUKKCBPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苄基哌嗪 、 5-(chloromethyl)-7-(2-chlorophenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以54%的产率得到5-((4-benzylpiperazin-1-yl)methyl)-7-(2-chlorophenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide
  参考文献：
  名称：

  The structure-based optimization of δ-sultone-fused pyrazoles as selective BuChE inhibitors

  摘要：

  Structure-based optimization was conducted to improve the potency and selectivity of BuChE inhibitors with delta-sulfonolactone-fused pyrazole scaffold. By mimicking the hydrophobic interactions of donepezil at PAS, the introduction of a tertiary benzylamine at 5-position can significantly increase BuChE inhibitory activity. Compounds C4 and C6 were identified as high selective nanomolar BuChE inhibitors (IC50 = 8.3 and 7.7 nM, respectively), which exhibited mild antioxidant capacity, nontoxicity, lipophilicity and neuroprotective activity. Kinetic studies showed that BuChE inhibition of compound C6 was mixed-type against BuChE (K-i = 24 nM) and >2000-fold selectivity for BuChE over AChE. The proposed binding mode of new inhibitors was consistent with the results of structure-activity relationship analysis. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112273
• 作为产物：
  描述：

  2-氯苯肼盐酸盐 在 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-(chloromethyl)-7-(2-chlorophenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide
  参考文献：
  名称：

  The structure-based optimization of δ-sultone-fused pyrazoles as selective BuChE inhibitors

  摘要：

  Structure-based optimization was conducted to improve the potency and selectivity of BuChE inhibitors with delta-sulfonolactone-fused pyrazole scaffold. By mimicking the hydrophobic interactions of donepezil at PAS, the introduction of a tertiary benzylamine at 5-position can significantly increase BuChE inhibitory activity. Compounds C4 and C6 were identified as high selective nanomolar BuChE inhibitors (IC50 = 8.3 and 7.7 nM, respectively), which exhibited mild antioxidant capacity, nontoxicity, lipophilicity and neuroprotective activity. Kinetic studies showed that BuChE inhibition of compound C6 was mixed-type against BuChE (K-i = 24 nM) and >2000-fold selectivity for BuChE over AChE. The proposed binding mode of new inhibitors was consistent with the results of structure-activity relationship analysis. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112273