methyl 3-(1H-indol-1-yl)propanoate | 76916-49-9

• 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: methyl 3-(1H-indol-1-yl)propanoate
• 英文别名: methyl 3-(1-indolyl)propionate；methyl 3-indol-1-ylpropanoate
• CAS: 76916-49-9
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD00087206
• 分子量: 203.241
• InChiKey: ILAGLZFPDDPGEI-UHFFFAOYSA-N

物化性质

• 沸点：
  341.6±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(1H-indol-1-yl)propanoate 在 ammonium acetate 、 肼 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 1-[2-(5,6-Dimethyl-1,2,4-triazin-3-yl)ethyl]indole
  参考文献：
  名称：

  Indole as a dienophile in inverse electron demand Diels-Alder reactions. 3. Intramolecular reactions with 1,2,4-triazines to access the canthine skeleton

  摘要：

  The intramolecular inverse electron demand cycloaddition of indole with 1,2,4-triazines connected by a tri- or tetramethylene tether linking the indole N-1 position with the triazinyl 3-position successfully produces the canthine skeleton and the homologous system with a seven-membered D-ring.

  DOI：

  10.1021/jo00046a005
• 作为产物：
  描述：

  3-phenylthioindole 在 苄基三甲基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 methyl 3-(1H-indol-1-yl)propanoate
  参考文献：
  名称：

  2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

  摘要：

  The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.

  DOI：

  10.1007/s10593-010-0504-3

文献信息

• [EN] INDOLYL-PIPERIDINYL BENZYLAMINES AS BETA-TRYPTASE INHIBITORS<br/>[FR] INDOLYL-PIPÉRIDINYL BENZYLAMINES INHIBITRICES DE LA BÊTA-TRYPTASE
  申请人：SANOFI SA

  公开号：WO2011079102A1

  公开（公告）日：2011-06-30

  The present invention discloses and claims a series of substituted indolyl-piperidinyl benzylamines of formula (I), wherein R1, R2 and R3 are as described herein. More specifically, the compounds of this invention are inhibitors of β-tryptase and are, therefore, useful as pharmaceutical agents. Additionally, this invention also discloses methods of preparation of substituted indolyl-piperidinyl benzylamines. In one of the embodiments, there is provided the compounds of formula (I) wherein R3 is (II).

  本发明公开并要求一系列取代的吲哚基-哌啶基苄胺化合物，其公式为（I），其中R1、R2和R3如本文所述。更具体地说，本发明的化合物是β-tryptase的抑制剂，因此可用作药物制剂。此外，本发明还公开了取代的吲哚基-哌啶基苄胺的制备方法。在其中一个实施例中，提供了公式（I）的化合物，其中R3是（II）。
• [EN] INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF<br/>[FR] DÉRIVÉS D'INDOLINE, COMPOSITIONS LES CONTENANT ET LEURS UTILISATIONS
  申请人：YISSUM RES DEV CO

  公开号：WO2017125932A1

  公开（公告）日：2017-07-27

  The present invention is directed to indoline derivatives and salts thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders associated with at least one of oxidative stress, an immune response, release of NO and release of pro-inflammatory cytokine.

  本发明涉及吲哚啉衍生物及其盐，包含它们的组合物以及它们用于治疗与氧化应激、免疫反应、NO释放和促炎细胞因子释放至少一种相关疾病和紊乱的用途。
• Synthesis and Biological Evaluation of Derivatives of Indoline as Highly Potent Antioxidant and Anti-inflammatory Agents
  作者：Shani Zeeli、Tehilla Weill、Efrat Finkin-Groner、Corina Bejar、Michal Melamed、Svetlana Furman、Michael Zhenin、Abraham Nudelman、Marta Weinstock

  DOI：10.1021/acs.jmedchem.8b00001

  日期：2018.5.10

  protected RAW264.7 macrophages against H2O2 induced cytotoxicity and LPS induced elevation of NO, TNF-α, and IL-6. Several derivatives had anti-inflammatory activity at 1/100th of the concentration of unsubstituted indoline. Four compounds with ester, amine, amide, or alcohol side chains injected subcutaneously in mice at a dose of 1 μmol/kg or less, like dexamethasone (5.6 μmol/kg) prevented LPS-induced

  我们描述了具有有效抗氧化剂和抗炎活性的新型吲哚啉衍生物的制备和评价，用于治疗与慢性炎症相关的病理状况。所述二氢吲哚在位置1被带有氨基，酯，酰胺或醇基的链取代，并且一些在苯并环上具有另外的取代基Cl，MeO，Me，F，HO或BnO。浓度为1 pM到1 nM的几种化合物可保护RAW264.7巨噬细胞免受H 2 O 2污染诱导的细胞毒性和LPS诱导的NO，TNF-α和IL-6升高。几种衍生物在未取代的吲哚啉浓度的1/100处具有抗炎活性。皮下注射剂量为1μmol/ kg或更低的四种带有酯，胺，酰胺或醇侧链的化合物，例如地塞米松（5.6μmol/ kg），可防止LPS诱导的脑和周围组织细胞因子升高。在观察的3天中，皮下注射100μmol/ kg的这些化合物不会对小鼠造成明显的不良影响。
• Olefin-Oriented Selective Synthesis of Linear and Branched N-Alkylated Heterocycles by Hydroamination
  作者：Sushmita、Trapti Aggarwal、Kapil Mohan Saini、Akhilesh K. Verma

  DOI：10.1002/ejoc.202000373

  日期：2020.6.16

  Selective base‐Mediated hydroamination of N‐heterocycles with olefins for the construction of Linear and branched N‐alkylated heterocycles is described. This protocol provided the synthesis of exclusive N‐alkylated product instead of the C‐3 Michael addition product.

  描述了N-杂环与烯烃的选择性碱介导加氢胺化反应，用于构建直链和支链N-烷基化杂环。该协议提供了专有的N-烷基化产物而不是C-3 Michael加成产物的合成。
• Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
  作者：Anguo Ying、Ming Zheng、Haidan Xu、Fangli Qiu、Changhua Ge

  DOI：10.1007/s11164-011-0296-9

  日期：2011.10

  An efficient and facile protocol for aza-Michael addition of aliphatic and aromatic amines to electron-deficit alkenes using [TMG][Lac] as catalyst under solvent-free conditions was established.

  建立了在无溶剂条件下使用[TMG] [Lac]作为催化剂，将脂肪族和芳香族胺类氮杂-迈克尔加成至缺电子烯烃的有效而简便的方法。