4-[(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide | 809275-28-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 4-[(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide
• 英文别名: 4-[(1R,5S)-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide；4-[(8-Azabicyclo[3.2.1]octan-3-ylidene)(bromo)methyl]-N-ethylbenzamide；4-[8-azabicyclo[3.2.1]octan-3-ylidene(bromo)methyl]-N-ethylbenzamide
• CAS: 809275-28-3；823816-32-6；823816-34-8
• 化学式: C₁₇H₂₁BrN₂O
• 分子量: 349.271
• InChiKey: AQQWNXBIUMNGDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide 在 四(三苯基膦)钯 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.27h， 生成 4-[[4-(Ethylcarbamoyl)phenyl]-[8-(furan-3-ylmethyl)-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]benzamide
  参考文献：
  名称：

  Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists

  摘要：

  Two parallel synthetic methods were developed to explore the structure-activity relationships (SAR) of a series of potent opioid agonists. This series of tropanylidene benzamides proved extremely tolerant of structural variation while maintaining excellent opioid activity. Evaluation of several representative compounds from this series in the mouse hot plate test revealed potent antinociceptive effects upon oral administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.004
• 作为产物：
  描述：

  3-[bromo-(4-ethylcarbamoyl-phenyl)-methylene]-(1R,5S)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester 在 TMSI 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 4-[(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide
  参考文献：
  名称：

  3-(diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives

  摘要：

  这项发明涉及3-(二芳基亚甲基)-8-氮杂双环[3.2.1]辛烷衍生物，可用作δ-阿片受体或μ-阿片受体调节剂。根据它们的激动剂或拮抗剂作用，这些化合物可用作镇痛剂、免疫抑制剂、抗炎药、用于治疗神经和精神疾病的药物、药物和酒精滥用的药物、治疗胃炎和腹泻的药物、心血管药物以及用于治疗呼吸系统疾病的药物。

  公开号：

  US20050004163A1

文献信息

• Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists
  作者：Steven J. Coats、Mark J. Schulz、John R. Carson、Ellen E. Codd、Dennis J. Hlasta、Philip M. Pitis、Dennis J. Stone、Sui-Po Zhang、Ray W. Colburn、Scott L. Dax

  DOI：10.1016/j.bmcl.2004.09.004

  日期：2004.11

  Two parallel synthetic methods were developed to explore the structure-activity relationships (SAR) of a series of potent opioid agonists. This series of tropanylidene benzamides proved extremely tolerant of structural variation while maintaining excellent opioid activity. Evaluation of several representative compounds from this series in the mouse hot plate test revealed potent antinociceptive effects upon oral administration. (C) 2004 Elsevier Ltd. All rights reserved.
• 3-(diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives
  申请人：Coats J. Steven

  公开号：US20050004163A1

  公开（公告）日：2005-01-06

  This invention is directed to 3-(diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives useful as δ-opioid or μ-opioid receptor modulators. Depending on their agonist or antagonist effect, the compounds are useful analgesics, immunosuppressants, antiinflammatory agents, agents for the treatment of neurological and psychiatric conditions, medicaments for drug and alcohol abuse, agents for treating gastritis and diarrhea, cardiovascular agents and agents for the treatment of respiratory diseases.

  这项发明涉及3-(二芳基亚甲基)-8-氮杂双环[3.2.1]辛烷衍生物，可用作δ-阿片受体或μ-阿片受体调节剂。根据它们的激动剂或拮抗剂作用，这些化合物可用作镇痛剂、免疫抑制剂、抗炎药、用于治疗神经和精神疾病的药物、药物和酒精滥用的药物、治疗胃炎和腹泻的药物、心血管药物以及用于治疗呼吸系统疾病的药物。