N,N'-Decamethylendi-(chloracetamid) | 33625-18-2

• 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'-Decamethylendi-(chloracetamid)
• 英文别名: 2-chloro-N-[10-[(2-chloroacetyl)amino]decyl]acetamide
• CAS: 33625-18-2
• 化学式: C₁₄H₂₆Cl₂N₂O₂
• 分子量: 325.279
• InChiKey: HCEYFNJUTSXSPK-UHFFFAOYSA-N

物化性质

• 沸点：
  526.9±35.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  20.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N'-Decamethylendi-(chloracetamid) 在 sodium azide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.01h， 生成 2-[4-[4-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxybutyl]triazol-1-yl]-N-[10-[[2-[4-[4-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxybutyl]triazol-1-yl]acetyl]amino]decyl]acetamide
  参考文献：
  名称：

  Size-Specific Ligands for RNA Hairpin Loops

  摘要：

  The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo.

  DOI：

  10.1021/ja051685b
• 作为产物：
  描述：

  癸二胺 、 氯乙酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 N,N'-Decamethylendi-(chloracetamid)
  参考文献：
  名称：

  Size-Specific Ligands for RNA Hairpin Loops

  摘要：

  The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo.

  DOI：

  10.1021/ja051685b

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.
• 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.
• 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：——
• Svetkin,Yu.V. et al., Journal of general chemistry of the USSR, 1976, vol. 46, p. 2031 - 2036
  作者：Svetkin,Yu.V. et al.

  DOI：——

  日期：——