3-(2-苯基-1H-吲哚-3-基)丙酸 | 62663-27-8

• 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
• 中文名称: 3-(2-苯基-1H-吲哚-3-基)丙酸
• 英文名称: 3-(2-phenyl-1H-indol-3-yl)-propionic acid
• 英文别名: 3-(2-phenyl-1H-indol-3-yl)propanoic acid；3-(2-phenyl-indol-3-yl)-propionic acid；Phenylindolyl-3-propionsaeure
• CAS: 62663-27-8
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: HLMMIHTXAONNJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-苯基-1H-吲哚-3-基)丙酸 在 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium tert-butylate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 45.15h， 生成 3-[3-(3-tert-butoxycarbonylamino-propyl)-2-phenyl-indol-1-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Combinatorial synthesis of substituted 3-(2-indolyl)piperidines and 2-phenyl indoles as inhibitors of ZipA–FtsZ interaction

  摘要：

  The ZipA-FtsZ protein-protein interaction is a potential target for antibacterial therapy. The design and parallel synthesis of a combinatorial library of small molecules, which target the FtsZ binding area on ZipA are described. Compounds were demonstrated to bind to the FtsZ binding domain of ZipA by HSQC NMR and to inhibit cell division in a cell elongation assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.031
• 作为产物：
  描述：

  苯乙酮 在 乙酸酐 、 溶剂黄146 作用下， 反应 24.42h， 生成 3-(2-苯基-1H-吲哚-3-基)丙酸
  参考文献：
  名称：

  Purohit, Shriram S.; Kamlesh, Ghori; Kumar, Devendra, Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 177 - 182

  摘要：

  DOI：

文献信息

• Synthesis of C-2 Arylated Tryptophan Amino Acids and Related Compounds through Palladium-Catalyzed C–H Activation
  作者：Sara Preciado、Lorena Mendive-Tapia、Fernando Albericio、Rodolfo Lavilla

  DOI：10.1021/jo400961x

  日期：2013.8.16

  Tryptophan (Trp) and tryptophan derivatives are C2-arylated. A C–H activation process allows the preparation of both protected and unprotected arylated-Trp amino acids, directly from the amino acid precursor and aryl iodides. The obtained compounds are suitable for standard solid-phase peptide synthesis.

  色氨酸（Trp）和色氨酸衍生物经过C2芳基化。AC–H活化过程可直接从氨基酸前体和芳基碘化物制备受保护和不受保护的芳基化Trp氨基酸。所获得的化合物适用于标准固相肽合成。
• Iodine(III)-Mediated C–C Bond Coupling to Construct Spirocyclic Indolenines of Various Ring Sizes
  作者：Yanren Zhu、Shaoxiong Yang、Enfan Pu、Li Li、Silei Ye、Longsheng Wei、Guolan Ma、Yushun Zhang、Hongbin Zhang、Jingbo Chen

  DOI：10.1021/acs.orglett.3c01106

  日期：2023.5.19

  iodine(III)-mediated intramolecular dearomative spirocyclization of indole derivatives to generate highly strained spirocyclobutyl, spirocyclopentyl, and spirocyclohexyl indolenines in moderate to good yields. A set of structurally novel, densely functionalized spiroindolenines with broad functional group compatibility was efficiently constructed in this way under mild reaction conditions. Moreover

  在此，我们报告了一种新型的碘 (III) 介导的吲哚衍生物的分子内脱芳环化螺环化，以中等至良好的收率生成高度应变的螺环丁基、螺环戊基和螺环己基吲哚啉。在温和的反应条件下，以这种方式有效地构建了一组具有广泛官能团相容性的结构新颖、密集官能化的螺吲哚。此外，β-烯胺酯作为产品中的多功能官能团，为生物活性化合物及相关天然产物的合成提供了极大的便利。
• NBS-induced intramolecular annulation reactions for the divergent synthesis of fused- and spirocyclic indolines
  作者：Xian Luo、Meng-Meng Xu、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1039/d3cc01920a

  日期：——

  have a great influence upon the reaction. By using C2-methyl- and C2-phenyl-3-(1H-indol-3-yl)-N-alkoxypropanamide as templates, practical protocols for the divergent synthesis of fused- and spirocyclic indoline compounds were studied and established.

  描述了NBS 诱导的 3-(1 H -indol-3-yl) -N -alkoxypropanamide 的分子内环化。在碱的帮助下，反应在温和的条件下进行得很好而且很快。发现3-(1H - indol-3-yl)-N - alkoxypropanamide中吲哚环上的C2-取代基对反应有很大的影响。以 C2-methyl- 和 C2-phenyl-3-(1 H -indol-3-yl) -N -alkoxypropanamide 为模板，研究并建立了稠环和螺环二氢吲哚化合物的发散合成实用方案。
• NERVE CELL PROTECTIVE AGENTS
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0858996A1

  公开（公告）日：1998-08-19

  The invention provides novel benzindole derivatives, processes for producing them, as well as a neuroprotective agent, an agent to prevent or treat diseases involving the degeneration, retraction or death of neurons, and an analgesic, each containing the benzindole derivatives as an active ingredient.

  本发明提供了新型苯并吲哚衍生物、生产工艺以及神经保护剂、预防或治疗涉及神经元变性、回缩或死亡的疾病的药物和镇痛剂，每种药物都含有苯并吲哚衍生物作为活性成分。
• INHIBITORS OF APOL1 AND METHODS OF USING SAME
  申请人：Vertex Pharmacéuticals Incorporated

  公开号：US20200377479A1

  公开（公告）日：2020-12-03

  The disclosure provides at least one entity chosen from compounds of formula (I), solid state forms of the same, compositions comprising the same, and methods of using the same, including use in treating focal segmental glomeulosclerosis (FSGS) and/or non-diabetic kidney disease (NDKD).