5-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indole-2,3-dione | 903200-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indole-2,3-dione
• 英文别名: 5-chloro-1-[2-(morpholin-4-yl)ethyl]-1H-indole-2,3-dione；5-chloro-1-(2-morpholin-4-ylethyl)indole-2,3-dione
• CAS: 903200-53-3
• 化学式: C₁₄H₁₅ClN₂O₃
• 分子量: 294.738
• InChiKey: KZGMYZWNEHEETJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indole-2,3-dione 、 1-萘胺 以 乙醇 为溶剂， 反应 4.0h， 以68%的产率得到5-chloro-3-(naphthalen-1-ylimino)-1-(2-morpholin-4-yl-ethyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Analogs of Indole-Based Cannabimimetic Agents

  摘要：

  Aminoalkylindoles (AAIs), although structurally dissimilar from the classical cannabinoids, are known to be capable of binding to cannabinoid receptors and of evoking cannabinomimetic responses. With the aim of investigating the structure–activity relationships (SAR) for the binding of non‐classical agonists to CB1 and CB2 cannabinoid receptors, we designed and synthesized a series of indole derivatives. The compounds were tested for their analgesic action by formalin test and compared to WIN 55212‐2, an AAI acting to the cannabinoid receptors. In receptor binding assay, compound 5 showed affinity for the CB1 receptor comparable to WIN 55212‐2.

  DOI：

  10.1111/j.1747-0285.2009.00910.x
• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 、 5-氯靛红 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 5-chloro-1-(2-morpholin-4-yl-ethyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  新型吗啉化靛红-喹啉杂化物作为有效抗乳腺癌药物的设计、合成和生物学评价

  摘要：

  考虑到对有效和更安全的抗乳腺癌药物的新兴需求以及靛红、喹诺酮和吗啉衍生物的药理特性，设计、合成和评估了新型肼连接的吗啉化靛红-喹啉杂化物作为抗乳腺癌药物抗癌剂。合成的杂合化合物针对两种乳腺癌细胞系（MCF-7 和 MDA-MB-231）进行了初步筛选。几乎所有合成物都显示出对激素阳性 MCF-7 细胞的有效抑制潜力，而对激素阴性 MDA-MB-231 细胞无活性。有效化合物针对 L929（非癌性皮肤成纤维细胞）细胞系进行了进一步评估，发现其对 MCF-7 细胞的选择性高于 L929 细胞。细胞周期分析证实最有效的化合物AS-4(MCF-7: GI 50 = 4.36 µM) 在 G 2 /M 阶段 导致有丝分裂停滞。由于对雌激素受体α (ERα) 依赖性 MCF-7 细胞具有更高的选择性，AS-4与 ERα 的各种结合相互作用也得到简化，表明AS-4具有完全阻断 ERα 的能力。总体而言，

  DOI：

  10.1002/ardp.202100368

文献信息

• Synthesis and Pharmacological Evaluation of Analogs of Indole-Based Cannabimimetic Agents
  作者：Orazio Mazzoni、Maria V. Diurno、Antonio M. di Bosco、Ettore Novellino、Paolo Grieco、Giovanni Esposito、Alessia Bertamino、Antonio Calignano、Roberto Russo

  DOI：10.1111/j.1747-0285.2009.00910.x

  日期：2010.1

  Aminoalkylindoles (AAIs), although structurally dissimilar from the classical cannabinoids, are known to be capable of binding to cannabinoid receptors and of evoking cannabinomimetic responses. With the aim of investigating the structure–activity relationships (SAR) for the binding of non‐classical agonists to CB1 and CB2 cannabinoid receptors, we designed and synthesized a series of indole derivatives. The compounds were tested for their analgesic action by formalin test and compared to WIN 55212‐2, an AAI acting to the cannabinoid receptors. In receptor binding assay, compound 5 showed affinity for the CB1 receptor comparable to WIN 55212‐2.
• Design, synthesis, and biological evaluation of novel morpholinated isatin–quinoline hybrids as potent anti‐breast cancer agents
  作者：Atamjit Singh、Harneetpal Kaur、Saroj Arora、Preet Mohinder Singh Bedi

  DOI：10.1002/ardp.202100368

  日期：2022.2

  the emerging need for potent and safer anti-breast cancer agents as well as the pharmacological attributes of isatin, quinolone, and morpholine derivatives, novel hydrazine-linked morpholinated isatin–quinoline hybrids were designed, synthesized, and evaluated as anti-breast cancer agents. The synthesized hybrid compounds were preliminarily screened against two breast cancer cell lines (MCF-7 and MDA-MB-231)

  考虑到对有效和更安全的抗乳腺癌药物的新兴需求以及靛红、喹诺酮和吗啉衍生物的药理特性，设计、合成和评估了新型肼连接的吗啉化靛红-喹啉杂化物作为抗乳腺癌药物抗癌剂。合成的杂合化合物针对两种乳腺癌细胞系（MCF-7 和 MDA-MB-231）进行了初步筛选。几乎所有合成物都显示出对激素阳性 MCF-7 细胞的有效抑制潜力，而对激素阴性 MDA-MB-231 细胞无活性。有效化合物针对 L929（非癌性皮肤成纤维细胞）细胞系进行了进一步评估，发现其对 MCF-7 细胞的选择性高于 L929 细胞。细胞周期分析证实最有效的化合物AS-4(MCF-7: GI 50 = 4.36 µM) 在 G 2 /M 阶段 导致有丝分裂停滞。由于对雌激素受体α (ERα) 依赖性 MCF-7 细胞具有更高的选择性，AS-4与 ERα 的各种结合相互作用也得到简化，表明AS-4具有完全阻断 ERα 的能力。总体而言，