2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole | 1415702-13-4

• 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: 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
• 英文别名: 1H-Indole, 2-(4,5-dihydro-1H-imidazol-2-yl)-
• CAS: 1415702-13-4
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: RFUSGALWQQKBEW-UHFFFAOYSA-N

物化性质

• 沸点：
  392.7±34.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole 在 碘苯二乙酸 、 sodium hydride 、 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 25.0~110.0 ℃ 、1.72 MPa 条件下， 反应 12.22h， 生成 2-(1H-imidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole
  参考文献：
  名称：

  Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors

  摘要：

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

  DOI：

  10.1021/jm3013097
• 作为产物：
  描述：

  1-(pyrimidin-2-yl)-1H-indole-2-carbonitrile 在 sodium ethanolate 、 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole
  参考文献：
  名称：

  铜催化芳烃C ？H键氰化由C ？惰性乙腈的CN键裂解

  摘要：

  剪切和粘贴！已开发出一种通过CCN裂解的乙腈为腈源的Cu催化的芳族CH氰化反应（参见方案； TMEDA = N，N，N ′，N′-四甲基乙二胺）。该反应在铜中是催化的，发现使用（Me 3 Si）2作为添加剂在促进CCN裂解和提高反应速率方面起着关键作用。

  DOI：

  10.1002/chem.201303637

文献信息

• Hypoglycemic imidazoline compounds
  申请人：——

  公开号：US20040009976A1

  公开（公告）日：2004-01-15

  This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.

  这项发明涉及某些新型咪唑啉化合物及其类似物，它们用于治疗糖尿病、糖尿病并发症、代谢紊乱或相关疾病，其中存在葡萄糖代谢障碍，以及包含它们的药物组合物，以及它们的制备方法。
• Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source
  作者：Muhammad Siddique Ahmad、Kamel Meguellati、Zahid Shafiq

  DOI：10.1055/a-1770-8592

  日期：2022.7

  commercially available aryldiazonium tetrafluoroborate derivatives with 2-(piperidin-1-yl)acetonitrile (an organic cyano reagent) under mild conditions. This process utilizes a Pd/(Me3Si)2 system and is applied to a wide scope of aromatic diazonium substrates to give the corresponding nitrile-containing products in moderate to high yields (59–92%). This methodology is employed for the preparation of etravirine

  本研究描述了在温和条件下用 2-(哌啶-1-基)乙腈（一种有机氰基试剂）对市售芳基重氮四氟硼酸盐衍生物进行一锅催化氰化。该工艺利用 Pd/(Me 3 Si) 2系统，并应用于范围广泛的芳族重氮底物，以中等至高产率 (59-92%) 得到相应的含腈产品。该方法用于制备用于治疗 HIV 的药物依曲韦林，以及转化 1 H-indole-2-carbonitrile 转化为用作 NMDA 受体拮抗剂的化合物，并且对 HIV 突变株具有很高的潜力。为这种 Pd 催化的氰化提出的机制涉及氰化物离子，正如使用试纸所证实的那样。
• 3-Imidazolyl-Indoles for the Treatment of Proliferative Diseases
  申请人：Boettcher Andreas

  公开号：US20100125064A1

  公开（公告）日：2010-05-20

  The invention relates to 3-heterocyclyl indolyl compounds capable of inhibiting the interaction between p53, or variants thereof, and MDM2 and/or MDM4, or variants thereof, respectively, said compounds having the formula I, wherein R 1 , R 2 , R 3 , R 4 , R A , Y and Y are as defined in the specification. Due to their activity, the compounds are useful in the treatment of various disorders and diseases mediated by the activity of MDM2 and/or MDM4, or variants thereof, such as inflammatory or proliferative diseases or in the protection of cells.

  本发明涉及能够抑制p53或其变体与MDM2和/或MDM4或其变体相互作用的3-杂环基吲哚化合物，其中所述化合物具有式I，其中R1、R2、R3、R4、RA、Y和Y的定义见说明书。由于其活性，这些化合物可用于治疗由MDM2和/或MDM4或其变体介导的各种疾病和疾病，例如炎症性或增殖性疾病或细胞保护。
• Synthesis, antimicrobial activity, and molecular docking study of fluorine-substituted indole-based imidazolines
  作者：Humberto L. Mendoza-Figueroa、Maria Trinidad Serrano-Alva、Gerardo Aparicio-Ozores、Gelacio Martínez-Gudiño、Oscar R. Suárez-Castillo、Nadia A. Pérez-Rojas、Martha S. Morales-Ríos

  DOI：10.1007/s00044-018-2177-x

  日期：2018.6

  A series of 2- or 3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole derivatives were synthesized, characterized, and evaluated for their in vitro antibacterial and antifungal activities. Additionally, the synthesized compounds were docked into the II DNA gyrase B active site, and their predicted binding modes were inspected. Inhibitory activity were tested against two species of Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), two species of Gram-positive bacteria (Staphylococcus aureus, Listeria monocytogenes) and two fungi (Candida albicans, Aspergillus niger) using the broth microdilution method. The fluorine-substituted 2-(2-imidazolyl)indole 2b was found to be the most potent antibacterial compound against E. coli and S. aureus strains (MIC value 80 mu g/mL). Compounds showed better activity against Gram-positive bacteria compared to Gram-negative bacteria. The docking results predicted that the imidazoline-indole hybrid moiety bind to the active site protein ATP-binding pocket from E. coli and S. aureus with good interaction energy scores. The significant loss of antibacterial activity for some imidazoline-indole analogs could be attributed to several nonoptimal enzyme interactions, including poor hydrogen bonds provided by Asp73 (E. coli gyrase numbering) or Asp81 (S. aureus gyrase numbering) and an associated water molecule.
• 3-(Imidazol-1-ylalkyl)indoles as selective inhibitors of thromboxane synthetase,pharmaceutical compositions thereof, and methods for preparing them
  申请人：Pfizer Limited

  公开号：EP0003901B1

  公开（公告）日：1981-08-05