N'-(3,4-dichlorobenzyl)-N,N-dimethylethane-1,2-diamine | 91429-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(3,4-dichlorobenzyl)-N,N-dimethylethane-1,2-diamine
• 英文别名: N-[(3,4-dichlorophenyl)methyl]-N',N'-dimethylethane-1,2-diamine
• CAS: 91429-04-8
• 化学式: C₁₁H₁₆Cl₂N₂
• 分子量: 247.167
• InChiKey: NYSHFAAKOUWIBE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.8±32.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-3-(4-fluorophenyl)imidazo[1,2-a]pyridine-2-carboxylic acid 、 N'-(3,4-dichlorobenzyl)-N,N-dimethylethane-1,2-diamine 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到5-bromo-N-(3,4-dichlorobenzyl)-N-[2-(dimethylamino)ethyl]-3-(4-fluorophenyl)imidazo[1,2-a]pyridine-2-carboxamide
  参考文献：
  名称：

  Synthetic studies of centromere-associated protein-E (CENP-E) inhibitors: 1.Exploration of fused bicyclic core scaffolds using electrostatic potential map

  摘要：

  Centromere-associated protein-E (CENP-E), a mitotic kinesin that plays an important role in mitotic progression, is an attractive target for cancer therapeutic drugs. For the purpose of developing novel CENP-E inhibitors as cancer therapeutics, we investigated a fused bicyclic compound identified by high throughput screening, 4-oxo-4,5-dihydrothieno[3,4-clpyridine-6-carboxamide la. Based on this scaffold, we designed inhibitors for efficient binding at the L5 site in CENP-E utilizing homology modeling as well as electrostatic potential map (EPM) analysis to enhance CENP-E inhibitory activity. This resulted in a new lead, 5-bromoimidazo[l,2-a]pyridine 7, which showed potent CENP-E enzyme inhibition (IC50: 50 nM) and cellular activity with accumulation of phosphorylated histone H3 in HeLa cells. Our homology model and EPM analysis proved to be useful tools for the rational design of CENP-E inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.067
• 作为产物：
  描述：

  N,N-二甲基乙二胺 、 3,4-二氯苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93.2%的产率得到N'-(3,4-dichlorobenzyl)-N,N-dimethylethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and algicidal activity of new dichlorobenzylamine derivatives against harmful red tides

  摘要：

  在本研究中，我们合成了65种二氯苄胺衍生物，并研究了它们对有害赤潮的藻类灭杀活性。3,4-二氯苄胺衍生物对多刺菱形藻、赤潮藻、海洋Chattonella以及圆形裙藻显示出较高的活性，而合成的化合物27、28、33、34、35和36在0.1 ~ 1.0 μM LC50条件下，在24小时后对这四种有害藻类展现出最高的藻类灭杀活性。为了验证这些化合物的安全性，我们进行了使用水蚤（Daphnia magna）和斑马鱼（Danio rerio）的急性生态毒理学测试，结果表明化合物33和34并不有害，因为目标生物在15 μM浓度下显示出较高的生存率。这些结果表明化合物33和34适合作为控制有害藻类的物质。

  DOI：

  10.1007/s12257-016-0175-8

文献信息

• COMPOSITION FOR DESTRUCTION OF MICROALGAE OR SPHAEROCARPUS
  申请人：CUREARTH, INC.

  公开号：US20180271091A1

  公开（公告）日：2018-09-27

  The present disclosure relates to a composition for the destruction of microalgae or mosses. The composition for the destruction of microalgae or mosses may suppress the growth and proliferation of microalgae when treated in moss cultivation facilities, marine microalgae cultivation facilities, areas in which green or red tide is occurring, or areas in which green or red tide is expected to occur, thereby preventing damage caused by the green or red tide.

  本公开涉及一种用于消灭微藻或苔藓的组合物。该用于消灭微藻或苔藓的组合物在苔藓培育设施、海洋微藻培育设施、发生绿潮或红潮的区域，或者预计会发生绿潮或红潮的区域中处理时，可以抑制微藻的生长和繁殖，从而预防绿潮或红潮造成的损害。
• Composition for destruction of microalgae or sphaerocarpus
  申请人：CUREARTH, INC.

  公开号：US11044909B2

  公开（公告）日：2021-06-29

  The present disclosure relates to a composition for the destruction of microalgae or mosses. The composition for the destruction of microalgae or mosses may suppress the growth and proliferation of microalgae when treated in moss cultivation facilities, marine microalgae cultivation facilities, areas in which green or red tide is occurring, or areas in which green or red tide is expected to occur, thereby preventing damage caused by the green or red tide.

  本公开涉及一种用于消灭微藻或苔藓的组合物。在苔藓栽培设施、海洋微藻栽培设施、正在发生绿潮或赤潮的地区或预计会发生绿潮或赤潮的地区处理这种用于消灭微藻或苔藓的组合物时，可抑制微藻的生长和增殖，从而防止绿潮或赤潮造成的损害。
• Synthetic Studies on Centromere-Associated Protein-E (CENP-E) Inhibitors: 2. Application of Electrostatic Potential Map (EPM) and Structure-Based Modeling to Imidazo[1,2-<i>a</i>]pyridine Derivatives as Anti-Tumor Agents
  作者：Takaharu Hirayama、Masanori Okaniwa、Hiroshi Banno、Hiroyuki Kakei、Akihiro Ohashi、Kenichi Iwai、Momoko Ohori、Kouji Mori、Mika Gotou、Tomohiro Kawamoto、Akihiro Yokota、Tomoyasu Ishikawa

  DOI：10.1021/acs.jmedchem.5b00836

  日期：2015.10.22

  To develop centromere-associated protein-E (CENP-E) inhibitors for use as anticancer therapeutics, we designed novel imidazo[1,2-a]pyridines, utilizing previously discovered 5-bromo derivative la. By site-directed mutagenesis analysis, we confirmed the ligand binding site. A docking model revealed the structurally important molecular features for effective interaction with CENP-E and could explain the superiority of the inhibitor (S)-isomer in CENP-E inhibition vs the (R)-isomer based on the ligand conformation in the LS loop region. Additionally, electrostatic potential map (EPM) analysis was employed as a ligand-based approach to optimize functional groups on the imidazo[1,2-a]pyridine scaffold. These a]pyridine derivative (+)-(S)-12, which showed potent CENP-E (p-HH3) elevation (EC50: 180 nM), and growth inhibition demonstrated antitumor activity (T/C: 40%, at 75 mg/kg) in a efforts led to the identification of the 5-methoxy imidazo [1,2-inhibition (IC50: 3.6 nM), cellular phosphorylated histone H3 (GI(50): 130 nM) in HeLa cells. Furthermore, (+)-(S)-12 human colorectal cancer Colo205 xenograft model in mice.
• [EN] COMPOSITION FOR DESTRUCTION OF MICROALGAE OR SPHAEROCARPUS<br/>[FR] COMPOSITION POUR LA DESTRUCTION DE MICROALGUES OU DE SPHAEROCARPUS<br/>[KO] 미세조류 또는 이끼류 파괴용 조성물
  申请人：CUREARTH INC

  公开号：WO2017065401A1

  公开（公告）日：2017-04-20

  본 개시는 미세조류 또는 이끼류 파괴용 조성물에 관한 것으로, 상기 미세조류 또는 이끼류 파괴용 조성물은 이끼류 배양장, 해양 미세조류 배양장, 녹조 또는 적조가 발생된 지역 또는 녹조나 적조 발생 예상 지역에 처리되어 미세조류의 생장 및 증식을 억제함으로써, 녹조 및 적조 피해를 예방할 수 있는 효과가 있다.