1-(5-氟-1H-吲哚-3-基)乙酮 | 99532-53-3

• 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
• 中文名称: 1-(5-氟-1H-吲哚-3-基)乙酮
• 英文名称: 5-fluoro-3-acetylindole
• 英文别名: 3-acetyl-5-fluoroindole；1-(5-fluoro-1H-indol-3-yl)ethanone；3-acetyl-5-fluoro-1H-indole；1-(5-fluoro-1H-indol-3-yl)ethan-1-one
• CAS: 99532-53-3
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: FYSYTQMPBWFSBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-氟-1H-吲哚-3-基)乙酮 在 盐酸 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  COMBINATION OF IAP INHIBITOR AND IMMUNE CHECKPOINT INHIBITOR

  摘要：

  本发明涉及一种由式(I)所表示的化合物、其异构体或其药学上可接受的盐的组合物，其用作IAP抑制剂，以及免疫检查点抑制剂的组合物；以及该组合物在制备癌症治疗药物中的应用。

  公开号：

  US20220175917A1
• 作为产物：
  描述：

  5-氟吲哚-2-甲酸 在 喹啉 、 铜 、 溶剂黄146 作用下， 反应 23.0h， 生成 1-(5-氟-1H-吲哚-3-基)乙酮
  参考文献：
  名称：

  Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives in vitro

  摘要：

  A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 x 10(3)- and 2.0 x 10(3)- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 mu M), respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.055

文献信息

• Towards the syntheses of<i>N</i>-H and<i>N</i>-alkylated derivatives of meridianins
  作者：Bernard Corbel、FrançOis Michaud、Laurent Meijer、Gaëlle Simon、Hélène Couthon-Gourves、Jean-Pierre Haelters、Nelly Kervarec

  DOI：10.1002/jhet.5570440407

  日期：2007.7

  Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved

  通过使用DMF-DMA将N-甲苯磺酰基-3-乙酰基吲哚或N-烷基-3-乙酰基吲哚经两步转化为相应的烯胺酮，合成了经络胺的新型N- H和N-烷基化衍生物作为潜在的抗肿瘤药。或不添加吡咯烷。用胍进一步环化得到相应的2-氨基嘧啶。由此获得的化合物的结构通过1 H和13 C NMR光谱，NOE实验和X射线分析证明。
• Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions
  作者：Saurabh Maity、Ujjwal Karmakar、Rajarshi Samanta

  DOI：10.1039/c7cc07086a

  日期：——

  Rh(III)catalyzed general strategy was developed for the site selective remote C4 (sp2) and C2 (sp3)-methyl thiolation of indole core keeping the oxime directing group at the C3 position. The transformation was accomplished under mild conditions with wide scope and functional group tolerance. The directing group can easily be removed after operation. Methyl substitution at the C2 position of indole core

  一种直接的Rh（III）催化的一般策略是针对吲哚核的位点选择性远程C4（sp 2）和C2（sp 3）-甲基硫醇化而开发的，将肟导向基团保持在C3位置。该转化是在温和条件下完成的，具有宽范围和官能团耐受性。引导组可以在操作后轻松移除。吲哚核的C2位置处的甲基取代导致C2（sp 3）-甲基硫醇化。
• Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone
  作者：Aniruddha Biswas、Rajarshi Samanta

  DOI：10.1002/ejoc.201701755

  日期：2018.3.29

  C4‐alkylation and C2‐annulation of indole derivative has been developed by using variable diazo esters. Fine tuning of the reactivity of diazo esters leads to control in regioselectivity with wide scope and functional‐group tolerance. A straightforward approach has been established to furnish an indolopyridone scaffold.

  通过使用可变的重氮酯开发了Rh III催化的吲哚衍生物的位点C4烷基化和C2环化。对重氮酯反应性的微调可以控制区域选择性，具有宽范围和官能团耐受性。已经建立了一种简单的方法来提供吲哚并吡啶酮支架。
• [EN] MALIC ENZYME INHIBITORS<br/>[FR] INHIBITEURS D'ENZYME MALIQUE
  申请人：SUN PHARMA ADVANCED RES CO LTD

  公开号：WO2021074898A1

  公开（公告）日：2021-04-22

  The present invention relates to novel compounds useful as malic enzyme (ME) inhibitors, processes for their preparation and use of these compounds for the therapeutic treatment of disorders mediated by ME such as cancers (e.g. pancreatic ductal adenocarcinoma (PDAC)) in humans.

  本发明涉及一种新型化合物，可用作苹果酸酶（ME）抑制剂，以及用于制备这些化合物的方法和利用这些化合物治疗由ME介导的疾病，如人类的癌症（例如胰腺导管腺癌（PDAC））。
• Brønsted acidic ionic liquid-promoted direct C3-acylation of <i>N</i>-unsubstituted indoles with acid anhydrides under microwave irradiation
  作者：Phuong Hoang Tran、Anh-Thanh Duy Nguyen、Hai Truong Nguyen、Thach Ngoc Le

  DOI：10.1039/c7ra11362e

  日期：——

  A green and efficient method for the synthesis of 3-acylindoles using a Brønsted acidic ionic liquid under microwave irradiation has been developed.

  使用布朗斯特酸性离子液体在微波辐射下合成3-酰基吲哚的一种绿色高效方法已经开发出来。