1-(4,5-二氯-2-硝基苯基)吡咯烷 | 59504-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(4,5-二氯-2-硝基苯基)吡咯烷
• 英文名称: 4,5-dichloro-2-(1-pyrrolidinyl)nitrobenzene
• 英文别名: 1-(4,5-Dichloro-2-nitrophenyl)pyrrolidine
• CAS: 59504-31-3
• 化学式: C₁₀H₁₀Cl₂N₂O₂
• 分子量: 261.108
• InChiKey: UGHSILWYVYUBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4,5-二氯-2-硝基苯基)吡咯烷 在 镍 sodium hydroxide 、 肼 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 5-Chloro-4-(pyridin-3-ylmethoxy)-2-pyrrolidin-1-yl-phenylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(2,4,5-trisubstituted phenyl)-3-(5-cyanopyrazin-2-yl)ureas as potent Chk1 kinase inhibitors

  摘要：

  Based on the X-ray crystallography of our lead compound 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-cyanopyrazin-2-yl) Urea ill the checkpoint kinase 1 (Chk1) enzyme, we modified R-4, and to a lesser extent, R-2, and R-5 of the phenyl ring, and made a variety of N-aryl-N'-pyrazinylurea Chk1 inhibitors. Enzymatic activity less than 20 nM was observed in 15 of 41 compounds. Compound 8i provided the best overall results in the cellular assays as it abrogated doxorubicin-induced cell cycle arrest (IC50=1.7 mu M) and enhanced doxorubicin cytotoxicity (IC50=0.44 mu M) while displaying no single agent activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.028
• 作为产物：
  描述：

  四氢吡咯 、 2,4,5-三氯硝基苯 以 乙腈 为溶剂， 反应 3.0h， 生成 1-(4,5-二氯-2-硝基苯基)吡咯烷
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(2,4,5-trisubstituted phenyl)-3-(5-cyanopyrazin-2-yl)ureas as potent Chk1 kinase inhibitors

  摘要：

  Based on the X-ray crystallography of our lead compound 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-cyanopyrazin-2-yl) Urea ill the checkpoint kinase 1 (Chk1) enzyme, we modified R-4, and to a lesser extent, R-2, and R-5 of the phenyl ring, and made a variety of N-aryl-N'-pyrazinylurea Chk1 inhibitors. Enzymatic activity less than 20 nM was observed in 15 of 41 compounds. Compound 8i provided the best overall results in the cellular assays as it abrogated doxorubicin-induced cell cycle arrest (IC50=1.7 mu M) and enhanced doxorubicin cytotoxicity (IC50=0.44 mu M) while displaying no single agent activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.028

文献信息

• Reaction of Mono-, Di-, and Trichloronitrobenzenes with<i>N</i>-Methyl Substituted Cyclic Tertiary Amines under High Pressure
  作者：Toshikazu Ibata、Muhong Shang、Tetsuo Demura

  DOI：10.1246/bcsj.68.2717

  日期：1995.9

  The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylpyrrolidine under high pressure gave products of demethylation and ring-opening through a quaternary pyrrolidinium chloride intermediate formed by the SNAr reaction. On the other hand, the reactions with 1-methylpiperidine and 4-methylmorpholine gave only demethylation products. The selectivities of the reactions of 1-methylpyrrolidine

  单-、二-和三氯硝基苯与 1-甲基吡咯烷在高压下反应，通过 SNAr 反应形成的季吡咯烷氯化物中间体产生去甲基化和开环产物。另一方面，与 1-甲基哌啶和 4-甲基吗啉的反应仅产生去甲基化产物。发现 1-甲基吡咯烷与这些氯硝基苯反应的选择性受吡咯烷鎓基团的相邻取代基的影响。
• Synthesis and biological evaluation of 1-(2,4,5-trisubstituted phenyl)-3-(5-cyanopyrazin-2-yl)ureas as potent Chk1 kinase inhibitors
  作者：Gaoquan Li、Lisa A. Hasvold、Zhi-Fu Tao、Gary T. Wang、Stephen L. Gwaltney、Jyoti Patel、Peter Kovar、Robert B. Credo、Zehan Chen、Haiying Zhang、Chang Park、Hing L. Sham、Thomas Sowin、Saul H. Rosenberg、Nan-Horng Lin

  DOI：10.1016/j.bmcl.2006.01.028

  日期：2006.4

  Based on the X-ray crystallography of our lead compound 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-cyanopyrazin-2-yl) Urea ill the checkpoint kinase 1 (Chk1) enzyme, we modified R-4, and to a lesser extent, R-2, and R-5 of the phenyl ring, and made a variety of N-aryl-N'-pyrazinylurea Chk1 inhibitors. Enzymatic activity less than 20 nM was observed in 15 of 41 compounds. Compound 8i provided the best overall results in the cellular assays as it abrogated doxorubicin-induced cell cycle arrest (IC50=1.7 mu M) and enhanced doxorubicin cytotoxicity (IC50=0.44 mu M) while displaying no single agent activity. (C) 2006 Elsevier Ltd. All rights reserved.