1-(6-bromohexyl)-5-methylindoline-2,3-dione | 1333514-63-8

• 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: 1-(6-bromohexyl)-5-methylindoline-2,3-dione
• 英文别名: 1-(6-Bromohexyl)-5-methyl-1H-indole-2,3-dione；1-(6-bromohexyl)-5-methylindole-2,3-dione
• CAS: 1333514-63-8
• 化学式: C₁₅H₁₈BrNO₂
• 分子量: 324.217
• InChiKey: BELMFEFRTAEVMR-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  451.3±55.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(6-bromohexyl)-5-methylindoline-2,3-dione 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.33h， 生成 3'-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazo-4-yl)-1-(6-(5-fluoro-2,3-dioxoindolin-1-yl)hexyl)-5-methylspiro[indoline-3,2'-thiazolidine]-2,4'-dione
  参考文献：
  名称：

  Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents

  摘要：

  A series of novel spiro[indole-thiazolidine]spiro[indole-pyran] derivatives were synthesized from N-(bromoalkyl)indol-2,3-diones via monospiro-bisindole intermediates; the two indole nuclei being connected via N-(CH2)(n)-N linker. Synthesized compounds were evaluated for their antimicrobial activities in vitro against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Staphylococcus epidermis), four Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, and Klebsiella pneumonia) as well as four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, and Candida albicans) using Cup plate method. Bis spiro-indoles exhibited stronger antibacterial and antifungal efficiency than their corresponding mono spiro-indoles. Compound 10e, the most active derivative was shown to inhibit the growth of all bacterial strains and two fungal strains (A. niger and C. albicans) (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.121
• 作为产物：
  描述：

  1,6-二溴己烷 、 5-甲基靛红 在 sodium hydride 作用下， 生成 1-(6-bromohexyl)-5-methylindoline-2,3-dione
  参考文献：
  名称：

  7-氯喹啉-isatin缀合物：抗疟疾，抗结核和细胞毒性评估

  摘要：

  通过直接亲核取代或Cu（II）Cl介导的曼尼希反应，已经合成了一系列二十个由哌嗪拴系的7-氯喹啉-依斯丁杂种。分别评估了这些新的缀合物对恶性疟原虫和结核分枝杆菌的氯喹耐药菌株的抗疟和抗结核功效，同时针对永久性小鼠胚胎成纤维细胞系3T6细胞系评估了细胞毒性谱。最有效的带IC的试验化合物50 0.22  μ米针对W2株恶性疟原虫和31.62  μ米 针对胚胎成纤维细胞的细胞系（细胞毒性）显示出较高的选择性指数143.73。

  DOI：

  10.1111/cbdd.12273

文献信息

• Eco-friendly polyethylene glycol (PEG-400): a green reaction medium for one-pot, four-component synthesis of novel asymmetrical bis-spirooxindole derivatives at room temperature
  作者：Alireza Hasaninejad、Maryam Beyrati

  DOI：10.1039/c7ra13133j

  日期：——

  PEG-400 has been used as a green and biodegradable polymeric solvent for the one-pot, two-step, multi-component synthesis of novel asymmetrical bis-spirooxindole derivatives by the reaction of N-alkyl isatin, isatin derivatives, alkylmalonates and C–H activated carbonyl compounds in the presence of K2CO3 at room temperature. Using this procedure, all the products were obtained in good to excellent

  PEG-400 已被用作绿色和可生物降解的聚合物溶剂，用于通过N-烷基靛红、靛红衍生物、烷基丙二酸酯和 C-反应一锅、两步、多组分合成新型不对称双螺吲哚衍生物。 H在室温下在 K 2 CO 3存在下活化羰基化合物。使用此程序，所有产品均以良好至优异的收率获得。
• Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies
  作者：Anu Rani、Gurjot Inder Singh、Ramandeep Kaur、Gabriella Palma、Shanen Perumal、Mandeep Kaur、Oluwakemi Ebenezer、Paul Awolade、Parvesh Singh、Vipan Kumar

  DOI：10.1016/j.jorganchem.2019.121072

  日期：2020.2

  with an IC50 value of 14.62 μM against MCF-7 and 79.63 μM against MDA-MB-231 cells, respectively. The observed anti-proliferative activities of active conjugates were further corroborated via docking studies carried out on estrogen receptor subtypes α and β.

  合成了一系列的1 H -1,2,3-三唑连接的二茂铁基-甲氧基-甲基-靛红共轭物，并测定了它们对雌激素反应性和非雌激素反应性细胞系的抗增殖活性。非细胞毒性缀合物7l具有最佳的辛基链间隔基和在isatin的C-5位置的甲基取代基的最佳组合，被证明是很有前途的产品，相对于MCF-7和IC.79 ，IC 50值分别为14.62μM和79.63μM分别针对MDA-MB-231细胞。通过对雌激素受体亚型α和β进行的对接研究进一步证实了所观察到的活性缀合物的抗增殖活性。