N,N'-Heptamethylendi-(chloracetamid) | 33625-20-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-Heptamethylendi-(chloracetamid)
• 英文别名: 2-chloro-N-[7-[(2-chloroacetyl)amino]heptyl]acetamide
• CAS: 33625-20-6
• 化学式: C₁₁H₂₀Cl₂N₂O₂
• 分子量: 283.198
• InChiKey: WLURQQYZBVSRPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-Heptamethylendi-(chloracetamid) 、 二硫代磷酸二乙酯 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以64%的产率得到O,O,O',O'-tetraethyl S,S'-2,2'-(heptane-1,7-diylbis(azanediyl))bis(2-oxoethane-2,1-diyl) diphosphorodithioate
  参考文献：
  名称：

  Bivalent Organophosphorus Compounds—Synthesis and Acetylcholinesterase Inhibitory Activity

  摘要：

  A series of novel symmetric S,S-2,2-(ethane-1,2-diylbis(azanediyl)) bis(2-oxoethane-2,1-diyl) O,O,O,O-tetraethyl diphosphorodithioate derivatives (12) was designed and synthesized based on the cluster effect and the multiple binding sites of acetylcholinesterase (AChE). The structures of all the newly synthesized title compounds were characterized by H-1 and C-13 NMR as well as elemental analyses. Their inhibitory activities against AChE were tested, and compound 12b exhibited the best activity (6.60-fold higher than ethion). The results suggested that the compound would bind to the catalytic center and the narrow gorge of the AChE simultaneously. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional table.

  DOI：

  10.1080/10426507.2012.736097
• 作为产物：
  描述：

  1,7-二氨基庚烷 、 氯乙酸甲酯 以 甲醇 为溶剂， 反应 10.0h， 生成 N,N'-Heptamethylendi-(chloracetamid)
  参考文献：
  名称：

  Bivalent Organophosphorus Compounds—Synthesis and Acetylcholinesterase Inhibitory Activity

  摘要：

  A series of novel symmetric S,S-2,2-(ethane-1,2-diylbis(azanediyl)) bis(2-oxoethane-2,1-diyl) O,O,O,O-tetraethyl diphosphorodithioate derivatives (12) was designed and synthesized based on the cluster effect and the multiple binding sites of acetylcholinesterase (AChE). The structures of all the newly synthesized title compounds were characterized by H-1 and C-13 NMR as well as elemental analyses. Their inhibitory activities against AChE were tested, and compound 12b exhibited the best activity (6.60-fold higher than ethion). The results suggested that the compound would bind to the catalytic center and the narrow gorge of the AChE simultaneously. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional table.

  DOI：

  10.1080/10426507.2012.736097

文献信息

• Design, synthesis and biological evaluation of organophosphorous-homodimers as dual binding site acetylcholinesterase inhibitors
  作者：Ruliang Xie、Qianfei Zhao、Tao Zhang、Jing Fang、Xiangdong Mei、Jun Ning、Yun Tang

  DOI：10.1016/j.bmc.2012.10.030

  日期：2013.1

  The cluster effect is an effective strategy to explore new lead compounds, and has been successfully applied in rational drug design and screening. A series of novel organophosphorous-homodimers were designed and synthesized based on the dual-site structure characteristics of acetylcholinesterase (AChE). The compounds were evaluated in vitro for their inhibitory activity to AChE extracted from Drosophila melanogaster and Musca domestic. Compound 4H showed an excellent inhibitor activity to both Drosophila melanogaster and Musca domestic with the corresponding IC50 values of 23 and 168 nM, respectively. Meanwhile, its activities against Drosophila melanogaster and Musca domestic AChE were more than 10,00,000 and 100,000-fold higher compared with the parent compound (MH), and was up to 245 and 107-fold higher than those of the positive control omethoate. The molecular docking study revealed that 4H possessed an optimal spacer length and can perfectly fit into the central pocket, active gorge, and peripheral site of DmAChE, and consequently exhibited highly improved inhibitor potency to DmAChE. The bioassay tests showed that 4 series compounds showed prominent insecticidal activities against both Lipaphser erysimi and Tetranychus cinnbarinus at a concentration of 200 mg/L. The insecticide activity of compound 4H was particularly significant that can cause 96% mortality to Tetranychus cinnbarinus after 24 h of treatment. (C) 2012 Elsevier Ltd. All rights reserved.
• Svetkin,Yu.V. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1192 - 1195
  作者：Svetkin,Yu.V. et al.

  DOI：——

  日期：——
• Bivalent Organophosphorus Compounds—Synthesis and Acetylcholinesterase Inhibitory Activity
  作者：Ruliang Xie、Ting Zhang、Qianfei Zhao、Tao Zhang、Xiangdong Mei、Huizhu Yuan、Jun Ning

  DOI：10.1080/10426507.2012.736097

  日期：2013.8.1

  A series of novel symmetric S,S-2,2-(ethane-1,2-diylbis(azanediyl)) bis(2-oxoethane-2,1-diyl) O,O,O,O-tetraethyl diphosphorodithioate derivatives (12) was designed and synthesized based on the cluster effect and the multiple binding sites of acetylcholinesterase (AChE). The structures of all the newly synthesized title compounds were characterized by H-1 and C-13 NMR as well as elemental analyses. Their inhibitory activities against AChE were tested, and compound 12b exhibited the best activity (6.60-fold higher than ethion). The results suggested that the compound would bind to the catalytic center and the narrow gorge of the AChE simultaneously. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional table.