1-benzyl-5-fluoro-1H-indole

• 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-benzyl-5-fluoro-1H-indole
• 英文别名: 1-benzyl-5-fluoroindole
• 化学式: C₁₅H₁₂FN
• 分子量: 225.265
• InChiKey: QZIAUKPDFYALKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-fluoro-1H-indole 在 N-碘代丁二酰亚胺 、 zinc trifluoromethanesulfonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  原位形成的 ICN 直接 C-H 氰化：Nannozinone B

  摘要：

  描述了一种使用 TMSCN、NIS 和 Zn(OTf) 2作为催化剂对不同吡喃、吡咯、吲哚和无环亲核双键进行 C-H 氰化的新方法。转化是在温和的条件下进行的，可以接受各种官能团。Zn(OTf) 2可能作为 TMSCN 和原位生成的碘化氰的活化剂发挥双重催化作用。报告了优化、底物范围和机械观察结果。此外，该方法应用于天然产物nannozinone B的首次全合成。

  DOI：

  10.1021/acs.orglett.3c00176
• 作为产物：
  描述：

  2-bromo-5-fluorophenylacetaldehyde 在 copper(l) iodide 、 K₃PO₄ 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 1-benzyl-5-fluoro-1H-indole
  参考文献：
  名称：

  Indoles Synthesized from Amines via Copper Catalysis

  摘要：

  N-Substituted indoles are synthesized from primary amines through a tandem reaction sequence. Initial condensation of the amine with an alpha-(o-haloaryl)ketone or aldehyde is followed by intramolecular aryl amination catalyzed by CuI. A variety of anilines and alkyl amines, including those with significant steric demands, are converted to indoles in high yields and with varying indole substitution.

  DOI：

  10.1021/ol400444g

文献信息

• Highly N²-Selective Coupling of 1,2,3-Triazoles with Indole and Pyrrole
  作者：Jian Wen、Li-Li Zhu、Qing-Wei Bi、Zhu-Qing Shen、Xiao-Xiao Li、Xin Li、Zhen Wang、Zili Chen

  DOI：10.1002/chem.201302761

  日期：2014.1.20

  Hydrogen‐bond mediated coupling of 1,2,3‐triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un‐, mono‐ and disubstituted triazoles and was applied to synthesize tryptophan derived fluorescent amino acids.

  氢键介导的1,2,3-三唑与吲哚和吡咯的偶合导致三唑部分的N2选择性官能化，产率中等至优异。该反应可耐受未取代，单取代和双取代的三唑，可用于合成色氨酸衍生的荧光氨基酸。
• Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation
  作者：Jannik C. Borghs、Viktoriia Zubar、Luis Miguel Azofra、Jan Sklyaruk、Magnus Rueping

  DOI：10.1021/acs.orglett.0c01270

  日期：2020.6.5

  base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisture-stable manganese catalyst provides access to either C3- or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen

  报道了使用容易获得的醇作为烷基化试剂的二氢吲哚的第一种贱金属催化的区域选择性脱氢烷基化。单一的空气和水分稳定的锰催化剂取决于所使用的溶剂，可提供C 3-或N-烷基化的吲哚的途径。机理研究表明，该反应通过无受体脱氢和氢自动转移策略的结合而发生。
• The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source
  作者：Bifu Liu、Min Liu、Qiang Li、Yuanhua Li、Kejun Feng、Yongbo Zhou

  DOI：10.1039/d0ob00485e

  日期：——

  The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C–H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C–CN bond cleavage.

  通过直接C-H官能化实现了无配体钯催化的吲哚C3-氰化。该协议利用 CH 3 CN 作为一种绿色且易于获得的氰化物源，通过过渡金属催化的 C-CN 键裂解以中等至良好的产率生产所需的产品。
• Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
  作者：Vladimir Iashin、Dénes Berta、Konstantin Chernichenko、Martin Nieger、Karina Moslova、Imre Pápai、Timo Repo

  DOI：10.1002/chem.202001436

  日期：2020.11.2

  Organoboron compounds are essential reagents in modern C−C coupling reactions. Their synthesis via catalytic C−H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal‐free synthesis of aryldifluoroboranes from BF3 and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic

  有机硼化合物是现代 C−C 偶联反应中必不可少的试剂。它们通过主族元素催化 C−H 硼基化的合成正在成为替代过渡金属催化的有力工具。在此，报道了从 BF 3和杂芳烃直接无金属合成芳基二氟硼烷。该反应由位阻胺和催化量的硫脲辅助。根据计算研究，该反应通过受挫路易斯对（FLP）机制进行。通过将获得的芳基二氟硼烷转化为相应的空气稳定的有机三氟硼酸四甲基铵，进一步稳定其免受破坏性的原脱硼化。
• Indole and 2,4-Thiazolidinedione conjugates as potential anticancer modulators
  作者：Domenica M. Corigliano、Riyaz Syed、Sebastiano Messineo、Antonio Lupia、Rahul Patel、Chittireddy Venkata Ramana Reddy、Pramod K. Dubey、Carmela Colica、Rosario Amato、Giovambattista De Sarro、Stefano Alcaro、Adisherla Indrasena、Antonio Brunetti

  DOI：10.7717/peerj.5386

  日期：——

  Thiazolidinediones (TZDs), also called glitazones, are five-membered carbon ring molecules commonly used for the management of insulin resistance and type 2 diabetes. Recently, many prospective studies have also documented the impact of these compounds as anti-proliferative agents, though several negative side effects such as hepatotoxicity, water retention and cardiac issues have been reported. In this work, we synthesized twenty-six new TZD analogues where the thiazolidinone moiety is directly connected to an N-heterocyclic ring in order to lower their toxic effects.

  By adopting a widely applicable synthetic method, twenty-six TZD derivatives were synthesized and tested for their antiproliferative activity in MTT and Wound healing assays with PC3 (prostate cancer) and MCF-7 (breast cancer) cells.

  Three compounds, out of twenty-six, significantly decreased cellular viability and migration, and these effects were even more pronounced when compared with rosiglitazone, a well-known member of the TZD class of antidiabetic agents. As revealed by Western blot analysis, part of this antiproliferative effect was supported by apoptosis studies evaluating BCL-xL and C-PARP protein expression.

  Our data highlight the promising potential of these TZD derivatives as anti-proliferative agents for the treatment of prostate and breast cancer.

  吡唑二酮类药物（TZDs），也称为格列酮，是常用于管理胰岛素抵抗和2型糖尿病的五元碳环分子。最近，许多前瞻性研究还记录了这些化合物作为抗增殖剂的影响，尽管已报告了一些负面副作用，如肝毒性、水潴留和心脏问题。在这项工作中，我们合成了二十六种新的TZD类似物，其中噻唑烷酮基团直接连接到N-杂环环，以降低其毒性作用。 通过采用一种广泛适用的合成方法，合成了二十六种TZD衍生物，并在MTT和伤口愈合实验中测试它们对PC3（前列腺癌）和MCF-7（乳腺癌）细胞的抗增殖活性。 在二十六种化合物中，有三种显著降低了细胞的存活率和迁移率，与罗格列酮（TZD类抗糖尿病药物的知名成员）相比，这些效应甚至更加显著。根据Western blot分析，部分这种抗增殖效应得到了通过评估BCL-xL和C-PARP蛋白表达的凋亡研究的支持。 我们的数据突显了这些TZD衍生物作为治疗前列腺癌和乳腺癌的抗增殖剂的潜在前景。