1-(cyclooctylmethyl)-4-[3-(ethoxycarbonylmethyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester | 873567-77-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(cyclooctylmethyl)-4-[3-(ethoxycarbonylmethyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
• CAS: 873567-77-2
• 化学式: C₂₇H₃₇N₃O₅
• 分子量: 483.608
• InChiKey: JDUNTHLDWLCNLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82.77
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(cyclooctylmethyl)-4-[3-(ethoxycarbonylmethyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到1-(1-Cyclooctylmethyl-5-hydroxymethyl-1,2,3,6-tetrahydro-pyridin-4-yl)-3-(2-hydroxy-ethyl)-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  Identification of an achiral analogue of J-113397 as potent nociceptin/orphanin FQ receptor antagonist

  摘要：

  To date, J-113397 represents the most potent and selective non peptide NOP receptor antagonist widely used in pharmacological studies. However, the synthesis, purification, and enantiomer separation of this molecule, which contains two chiral centers, is rather difficult and low-yielding. Here, we synthesized and tested a series of simplified J-113397 analogues to investigate the importance of the stereochemistry and the influence of the substituents at position 3 of the piperidine nucleus and on the nitrogen atom of the benzimidazolidinone nucleus. The compound coded as Trap-101, an achiral analogue of J-113397, combines a pharmacological profile similar to that of the parent compound with a practical, high-yielding preparation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.049
• 作为产物：
  描述：

  4-[(2-aminophenyl)amino]-1-(cyclooctylmethyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(cyclooctylmethyl)-4-[3-(ethoxycarbonylmethyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Identification of an achiral analogue of J-113397 as potent nociceptin/orphanin FQ receptor antagonist

  摘要：

  To date, J-113397 represents the most potent and selective non peptide NOP receptor antagonist widely used in pharmacological studies. However, the synthesis, purification, and enantiomer separation of this molecule, which contains two chiral centers, is rather difficult and low-yielding. Here, we synthesized and tested a series of simplified J-113397 analogues to investigate the importance of the stereochemistry and the influence of the substituents at position 3 of the piperidine nucleus and on the nitrogen atom of the benzimidazolidinone nucleus. The compound coded as Trap-101, an achiral analogue of J-113397, combines a pharmacological profile similar to that of the parent compound with a practical, high-yielding preparation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.049