1-benzyl-3-ethyl-1H-benzo[d]imidazol-2(3H)-one | 27509-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-benzyl-3-ethyl-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1-Benzoyl-3-ethyl-2-benzimidazolinon；1-benzyl-3-ethyl-1,3-dihydro-benzoimidazol-2-one；1-benzyl-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one；1-Benzyl-3-ethylbenzimidazol-2-one
• CAS: 27509-20-2
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: SFGGSFKSBNZWNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-benzyl-1H-benzo[d]imidazole 、 碘乙烷 在 咪唑 、 copper(l) iodide 、 二叔丁基过氧化物 、 三甲基乙酸 作用下， 以 正己烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以81%的产率得到1-benzyl-3-ethyl-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 7,9-Dialkylpurin-8-one Analogues: Broad Substrate Scope

  摘要：

  The one-pot and direct synthesis of 7,9-dialkylpurin-8-one analogues with broad substrate scope has been developed. This copper-catalyzed C-H oxidation reaction could avoid multistep synthesis of quaternary ammonium salts and expand the scope of halogenated alkanes. Moreover, benzimidazole derivatives are also applicable in the catalytic system.

  DOI：

  10.1021/jo402248d

文献信息

• Nociceptin analogs
  申请人：——

  公开号：US20030069249A1

  公开（公告）日：2003-04-10

  A compound of the formula (I), (II), (III) or (IV) 1 wherein Z, A, B, C, R, R 1 , R 2 , Q, and n are as described herein.

  一种化合物的公式(I)、(II)、(III)或(IV)，其中Z、A、B、C、R、R1、R2、Q和n的描述如下。
• 1-(4-AMINO-CYCLOHEXYL)-1,3-DIHYDRO-2H-BENZIMIDAZOLE-2-ONE DERIVATIVES AND RELATED COMPOUNDS AS NOCICEPTIN ANALOGS AND ORL1 LIGANDS FOR THE TREATMENT OF PAIN
  申请人：EURO-CELTIQUE S.A.

  公开号：EP1598339A1

  公开（公告）日：2005-11-23

  It is an object of certain embodiments of the present invention to provide compounds useful as analgesics, anti-anflammatories, diuretics, anesthetics and neuroprotective agents, anti-hypertensives, anti-anxioltics; agents for appetite control; hearing regulators; anti-tussives, anti-asthmatics, modulators of locomotor activity, modulators of learning and memory, regulators of neurotransmitter and hormone release, kidney function modulators, anti-depressants, agents to treat memory loss due to Alzheimer's disease or other dementias, anti-epileptics, anti-convulsants, agents to treat withdrawal from alcohol and drugs of addiction, agents to control water balance, agents to control sodium excretion and agents to control arterial blood pressure disorders and methods for administering said compounds. The compounds of the present invention are useful for modulating a pharmacodynamic response from one or more opioid receptors (ORL-1, µ, δ and κ) centrally and/or peripherally. The response can be attributed to the compound stimulating (agonist) or inhibiting (antagonist) the one or more receptors. Certain compounds can stimulate one receptor (e.g., a µ agonist) and inhibit a different receptor (e.g., an ORL-1 antagonist). The present invention in certain embodiments comprises compounds having the general formula (III): wherein D is a 5-8 membered cycloalkyl, 5-8 membered heterocyclic or a 6 membered aromatic or heteroaromatic group; the other substituents are defined in the claims.

  本发明某些实施方案的目的是提供可用作镇痛剂、抗炎剂、利尿剂、麻醉剂和神经保护剂、抗高血压剂、抗焦虑剂、食欲控制剂、听力调节剂的化合物；抗哮喘药、运动活动调节剂、学习和记忆调节剂、神经递质和激素释放调节剂、肾功能调节剂、抗抑郁药、治疗阿尔茨海默病或其他痴呆症引起的记忆力减退的药物、抗癫痫药、抗惊厥药、治疗戒酒和戒毒的药物、控制水平衡的药物、控制钠排泄的药物和控制动脉血压紊乱的药物以及施用上述化合物的方法。 本发明的化合物可用于调节一种或多种阿片受体（ORL-1、μ、δ 和 κ）在中枢和/或外周的药效学反应。这种反应可归因于化合物刺激（激动剂）或抑制（拮抗剂）一种或多种受体。某些化合物可以刺激一种受体（如 µ 激动剂），抑制另一种受体（如 ORL-1 拮抗剂）。 本发明在某些实施方案中包括具有通式(III)的化合物： 其中 D 是 5-8 个成员的环烷基、5-8 个成员的杂环基或 6 个成员的芳香族或杂芳香族基团； 其他取代基在权利要求中定义。
• 1-(4-piperidinyl)-1,3-dihydro-2h-benzoxazole-2-one derivatives and related compounds as nociceptin analogs and opioid receptor like receptor (ORL1) ligands for the treatment of pain
  申请人：EURO-CELTIQUE S.A.

  公开号：EP1918279A2

  公开（公告）日：2008-05-07

  A compound of formula (II), wherein Z,A,B,R,R1,R2,Q and n are described herein. It is an object of certain embodiments of the present invention to provide new compounds which exhibit affinity for the ORL1 receptor and one or more of the μ,δ or κ receptors for treating a patient suffering from chronic or acute pain.

  式 (II) 的化合物、 其中 Z、A、B、R、R1、R2、Q 和 n 如本文所述。 本发明某些实施方案的目的是提供对 ORL1 受体和一种或多种 μ、δ 或 κ 受体具有亲和力的新化合物，用于治疗慢性或急性疼痛患者。
• 1-(4-piperidinyl)-1,3-dihydro-2H-benzoxazole-2-one derivatives and related compounds as nociceptin analogs and ORL1 ligands for the treatment of pain
  申请人：EURO-CELTIQUE S.A.

  公开号：EP1930322A1

  公开（公告）日：2008-06-11

  It is an object of certain embodiments of the present invention to provide compounds useful as analgesics, anti-inflammatories, diuretics, anesthetics and neuroprotective agents, anti-hypertensives, anti-anxioltics, agents for appetite control; hearing regulators; anti-tussives; anti-asthmatics; modulators of locomotor activity, modulators of learning and memory, regulators of neurotransmitter and hormone release, kidney function modulators, antidepressants, agents to treat memory loss due to Alzheimer's disease, or other dementias, anti-epileptics, anti-convulsants, agents to treat withdrawal from alcohol and drugs of addiction, agents to control water balance, agents to control sodium excretion and agents to control arterial blood pressure disorders and methods for administering said compounds. The compounds of the present invention are useful for modulating a pharmacodynamic response from one or more opioid receptors (ORL-1, µ, δ and κ) centrally and/or peripherally. The response can be attributed to the compound stimulating (agonist) or inhibiting (antagonist) the one or more receptors. Certain compounds can stimulate one receptor (e.g., a µ agonist) and inhibit a different receptor (e.g., an ORL-1 antagonist). Other objects and advantages of the present invention will become apparent from the following detailed description thereof. The present invention in certain embodiments comprises compounds having the general formula (I): wherein D is a 5-8 membered cycloalkyl, 5-8 membered heterocyclic or a 6 membered aromatic or heteroaromatic group; the other substituents are defined in the claims.

  本发明某些实施方案的目的是提供可用作镇痛剂、抗炎剂、利尿剂、麻醉剂和神经保护剂、抗高血压剂、抗焦虑剂、食欲控制剂、听力调节剂、抗哮喘剂、运动活性调节剂、学习和记忆调节剂、神经递质和激素释放调节剂、肾功能调节剂、抗抑郁剂、治疗因记忆丧失而引起的记忆丧失的药物的化合物；运动活动调节剂、学习和记忆调节剂、神经递质和激素释放调节剂、肾功能调节剂、抗抑郁剂、治疗阿尔茨海默氏症或其他痴呆症引起的记忆力减退的药物、抗癫痫药、抗惊厥药、治疗戒酒和戒毒的药物、控制水平衡的药物、控制钠排泄的药物和控制动脉血压紊乱的药物以及给药上述化合物的方法。 本发明的化合物可用于调节一种或多种阿片受体（ORL-1、μ、δ 和 κ）在中枢和/或外周的药效学反应。这种反应可归因于化合物刺激（激动剂）或抑制（拮抗剂）一种或多种受体。某些化合物可以刺激一种受体（如μ激动剂），抑制另一种受体（如ORL-1拮抗剂）。 本发明的其它目的和优点将从下面的详细描述中显而易见。本发明在某些实施方案中包括具有通式(I)的化合物： 其中 D 是 5-8 个成员的环烷基、5-8 个成员的杂环基或 6 个成员的芳香族或杂芳香族基团； 其他取代基在权利要求中定义。
• 1-Piperidine-2-cyanoimino-1,3-dihydro-2H-benzimidazole derivatives as nociceptin analogs with ORL1 modulating activity for the treatment of pain
  申请人：EURO-CELTIQUE S.A.

  公开号：EP2050450A1

  公开（公告）日：2009-04-22

  Compounds of formula (IV) as ORL1 modulators for the treatment of pain.

  作为治疗疼痛的 ORL1 调节剂的式 (IV) 化合物。