2-(2-chloro-3-nitro-benzylamino)ethanol | 857040-81-4

• 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: 2-(2-chloro-3-nitro-benzylamino)ethanol
• 英文别名: 2-(2-chloro-3-nitrobenzylamino)ethanol；2-[(2-Chloro-3-nitrophenyl)methylamino]ethanol
• CAS: 857040-81-4
• 化学式: C₉H₁₁ClN₂O₃
• 分子量: 230.651
• InChiKey: QRSVRDFLEFUIMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-3-nitro-benzylamino)ethanol 在 palladium on activated charcoal sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 四丁基氟化铵 、 ammonium formate 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 叔丁醇 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  New Selective AT₂ Receptor Ligands Encompassing a γ-Turn Mimetic Replacing the Amino Acid Residues 4−5 of Angiotensin II Act as Agonists

  摘要：

  New benzodiazepine-based gamma-turn mimetics with one or two amino acid side chains were synthesized. The gamma-turn mimetics were incorporated into angiotensin II (Ang II) replacing the Val(3)-Tyr(4)-Ile(5) or Tyr(4)-Ile(5) peptide segments. All of the resulting pseudopeptides displayed high AT(2)/AT(1) receptor selectivity and exhibited AT(2) receptor affinity in the low nanomolar range. Molecular modeling was used to investigate whether the compounds binding to the AT(2) receptor could position important structural elements in common areas. A previously described benzodiazepine-based gamma-turn mimetic with high affinity for the AT(2) receptor was also included in the modeling. It was found that the molecules, although being structurally quite different, could adopt the same binding mode/interaction pattern in agreement with the model hypothesis. The pseudopeptides selected for agonist studies were shown to act as AT(2) receptor agonists being able to induce outgrowth of neurite cells, stimulate p42/p44(mapk), and suppress proliferation of PC12 cells.

  DOI：

  10.1021/jm0491492
• 作为产物：
  描述：

  2-氯-3-硝基苄醇 在 草酰氯 、 sodium cyanoborohydride 、 溶剂黄146 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 2-(2-chloro-3-nitro-benzylamino)ethanol
  参考文献：
  名称：

  新型假肽结合基于苯二氮卓的转模拟物—靶向结核分枝杆菌核糖核苷酸还原酶

  摘要：

  模仿结核分枝杆菌核糖核苷酸还原酶（RNR）小亚基（R2）C端的肽可以竞争与大亚基（R1）的结合，从而抑制RNR活性。此外，已经提出R 2 C末端的结合在M中非常相似。肺结核和鼠伤寒沙门氏菌。基于对S的完整络合物晶体结构的建模研究。鼠伤寒酶，确定了一个基于苯并二氮杂turn的转模拟物，并合成了一组结合了苯并二氮杂sc骨架的新化合物。在竞争性荧光偏振测定法和RNR活性测定法中评价化合物。这些研究表明，结合了苯二氮卓骨架的化合物具有竞争M的能力。肺结核R2的结合位点具有低微摩尔亲和力。

  DOI：

  10.1016/j.bmc.2013.01.020

文献信息

• Novel pseudopeptides incorporating a benzodiazepine-based turn mimetic—targeting Mycobacterium tuberculosis ribonucleotide reductase
  作者：Johanna Nurbo、Daniel J. Ericsson、Ulrika Rosenström、Daniel Muthas、Anna M. Jansson、Gunnar Lindeberg、Torsten Unge、Anders Karlén

  DOI：10.1016/j.bmc.2013.01.020

  日期：2013.4

  Peptides mimicking the C-terminus of the small subunit (R2) of Mycobacterium tuberculosis ribonucleotide reductase (RNR) can compete for binding to the large subunit (R1) and thus inhibit RNR activity. Moreover, it has been suggested that the binding of the R2 C-terminus is very similar in M. tuberculosis and Salmonella typhimurium. Based on modeling studies of a crystal structure of the holocomplex

  模仿结核分枝杆菌核糖核苷酸还原酶（RNR）小亚基（R2）C端的肽可以竞争与大亚基（R1）的结合，从而抑制RNR活性。此外，已经提出R 2 C末端的结合在M中非常相似。肺结核和鼠伤寒沙门氏菌。基于对S的完整络合物晶体结构的建模研究。鼠伤寒酶，确定了一个基于苯并二氮杂turn的转模拟物，并合成了一组结合了苯并二氮杂sc骨架的新化合物。在竞争性荧光偏振测定法和RNR活性测定法中评价化合物。这些研究表明，结合了苯二氮卓骨架的化合物具有竞争M的能力。肺结核R2的结合位点具有低微摩尔亲和力。
• New Selective AT₂ Receptor Ligands Encompassing a γ-Turn Mimetic Replacing the Amino Acid Residues 4−5 of Angiotensin II Act as Agonists
  作者：Ulrika Rosenström、Christian Sköld、Bianca Plouffe、Hélène Beaudry、Gunnar Lindeberg、Milad Botros、Fred Nyberg、Gunter Wolf、Anders Karlén、Nicole Gallo-Payet、Anders Hallberg

  DOI：10.1021/jm0491492

  日期：2005.6.1

  New benzodiazepine-based gamma-turn mimetics with one or two amino acid side chains were synthesized. The gamma-turn mimetics were incorporated into angiotensin II (Ang II) replacing the Val(3)-Tyr(4)-Ile(5) or Tyr(4)-Ile(5) peptide segments. All of the resulting pseudopeptides displayed high AT(2)/AT(1) receptor selectivity and exhibited AT(2) receptor affinity in the low nanomolar range. Molecular modeling was used to investigate whether the compounds binding to the AT(2) receptor could position important structural elements in common areas. A previously described benzodiazepine-based gamma-turn mimetic with high affinity for the AT(2) receptor was also included in the modeling. It was found that the molecules, although being structurally quite different, could adopt the same binding mode/interaction pattern in agreement with the model hypothesis. The pseudopeptides selected for agonist studies were shown to act as AT(2) receptor agonists being able to induce outgrowth of neurite cells, stimulate p42/p44(mapk), and suppress proliferation of PC12 cells.