(2-nitro-pyridin-3-yl)-(2-pyrrolidin-1-yl-ethyl)-amine | 55304-96-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2-nitro-pyridin-3-yl)-(2-pyrrolidin-1-yl-ethyl)-amine
• 英文别名: 2-nitro-N-(2-pyrrolidin-1-ylethyl)pyridin-3-amine
• CAS: 55304-96-6
• 化学式: C₁₁H₁₆N₄O₂
• mdl: MFCD26971499
• 分子量: 236.274
• InChiKey: ICTPDFMBWUIJCW-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-nitro-pyridin-3-yl)-(2-pyrrolidin-1-yl-ethyl)-amine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3-[2-(pyrrolidin-1-yl)ethyl]-3H-imidazo[4,5-b]pyridin-2-amine
  参考文献：
  名称：

  Optimisation of in silico derived 2-aminobenzimidazole hits as unprecedented selective kappa opioid receptor agonists

  摘要：

  Kappa opioid receptor (KOR) is an important mediator of pain signaling and it is targeted for the treatment of various pains. Pharmacophore based mining of databases led to the identification of 2-aminobenzimidazole derivative as KOR agonists with selectivity over the other opioid receptors DOR and MOR. A short SAR exploration with the objective of identifying more polar and hence less brain penetrant agonists is described herewith. Modeling studies of the recently published structures of KOR, DOR and MOR are used to explain the receptor selectivity. The synthesis, biological evaluation and SAR of novel benzimidazole derivatives as KOR agonists are described. The in vivo proof of principle for anti-nociceptive effect with a lead compound from this series is exemplified. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.064
• 作为产物：
  描述：

  1-(2-氨乙基)吡咯烷 、 2-氯-3-硝基吡啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (2-nitro-pyridin-3-yl)-(2-pyrrolidin-1-yl-ethyl)-amine
  参考文献：
  名称：

  Optimisation of in silico derived 2-aminobenzimidazole hits as unprecedented selective kappa opioid receptor agonists

  摘要：

  Kappa opioid receptor (KOR) is an important mediator of pain signaling and it is targeted for the treatment of various pains. Pharmacophore based mining of databases led to the identification of 2-aminobenzimidazole derivative as KOR agonists with selectivity over the other opioid receptors DOR and MOR. A short SAR exploration with the objective of identifying more polar and hence less brain penetrant agonists is described herewith. Modeling studies of the recently published structures of KOR, DOR and MOR are used to explain the receptor selectivity. The synthesis, biological evaluation and SAR of novel benzimidazole derivatives as KOR agonists are described. The in vivo proof of principle for anti-nociceptive effect with a lead compound from this series is exemplified. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.064

文献信息

• Optimisation of in silico derived 2-aminobenzimidazole hits as unprecedented selective kappa opioid receptor agonists
  作者：Pradip K. Sasmal、C. Vamsee Krishna、S. Sudheerkumar Adabala、M. Roshaiah、Khaji Abdul Rawoof、Emima Thadi、K. Pavan Sukumar、Srisailam Cheera、Chandrasekhar Abbineni、K.V.L. Narasimha Rao、A. Prasanthi、Kamal Nijhawan、Mahaboobi Jaleel、Lakshmi Ramachandran Iyer、T. Krishna Chaitanya、Nirbhay Kumar Tiwari、N. Lavanya Krishna、Vijay Potluri、Ish Khanna、Thomas M. Frimurer、Michael Lückmann、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2014.12.064

  日期：2015.2

  Kappa opioid receptor (KOR) is an important mediator of pain signaling and it is targeted for the treatment of various pains. Pharmacophore based mining of databases led to the identification of 2-aminobenzimidazole derivative as KOR agonists with selectivity over the other opioid receptors DOR and MOR. A short SAR exploration with the objective of identifying more polar and hence less brain penetrant agonists is described herewith. Modeling studies of the recently published structures of KOR, DOR and MOR are used to explain the receptor selectivity. The synthesis, biological evaluation and SAR of novel benzimidazole derivatives as KOR agonists are described. The in vivo proof of principle for anti-nociceptive effect with a lead compound from this series is exemplified. (C) 2014 Elsevier Ltd. All rights reserved.