5-氟-1-甲基-1H-吲哚-2-羧酸 | 167631-50-7

• 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: 5-氟-1-甲基-1H-吲哚-2-羧酸
• 英文名称: 5-fluoro-1-methyl-1H-indole-2-carboxylic acid
• 英文别名: 5-Fluoro-1-methylindole-2-carboxylic acid
• CAS: 167631-50-7
• 化学式: C₁₀H₈FNO₂
• mdl: MFCD03848204
• 分子量: 193.177
• InChiKey: ZOPXUHDPGGHISS-UHFFFAOYSA-N

物化性质

• 沸点：
  392.0±22.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-氟-1-甲基-1H-吲哚-2-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl 3-(5-fluoro-1-methyl-1H-indol-2-yl)-3-oxopropanoate
  参考文献：
  名称：

  Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex

  摘要：

  A Ni(NTf2)(2) and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.

  DOI：

  10.1021/acs.orglett.5b02497
• 作为产物：
  描述：

  5-氟-1-甲基-1H-吲哚-2-羧酸乙酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以90%的产率得到5-氟-1-甲基-1H-吲哚-2-羧酸
  参考文献：
  名称：

  New indole–isoxazolone derivatives: Synthesis, characterisation and in vitro SIRT1 inhibition studies

  摘要：

  A new series of indole-isoxazolone hybrids bearing substituted amide, substituted [(1,2,3-triazol-4-yl) methoxy]methyl group or substituted benzylic ether at position-2 of the indole nucleus was synthesised using a facile synthetic route and the molecules were characterised using spectroscopic techniques. The molecules were screened against three human cancer cell lines to evaluate their in vitro cytotoxic property. Most of the trifluoromethyl substituted derivatives exhibited better growth inhibition activity than their methyl substituted analogues. The SIRT1 inhibition activity of two potent molecules (I17 and I18) was investigated and the SIRT1 IC50 values are 35.25 and 37.36 mu M, respectively for I17 and I18. The molecular docking studies with SIRT1 enzyme revealed favourable interactions of the molecule I17 with the amino acids constituting the receptor enzyme. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.015

文献信息

• C-terminal modified (N-substituted)-2-indolyl dipeptides as inhibitors
  申请人：——

  公开号：US05877197A1

  公开（公告）日：1999-03-02

  This invention is directed to novel (N-substituted)indole ICE/ced-3-inhibitor compounds. The invention is also directed to pharmaceutical compositions of such indole compounds, plus the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, and for the treatment of ischemic injury.

  这项发明涉及新型的（N-取代）吲哚ICE/ced-3抑制剂化合物。该发明还涉及这些吲哚化合物的药物组合物，以及将这些组合物用于治疗患有炎症、自身免疫和神经退行性疾病的病人，以及用于治疗缺血性损伤。
• PHARMACEUTICAL COMPOSITION AND THE USE THEREOF, AND APPLICATION REGIME OF SAID PHARMACEUTICAL COMPOSITION FOR ON-DEMAND CONTRACEPTION
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160089364A1

  公开（公告）日：2016-03-31

  The invention relates to a pharmaceutical composition for non-hormonal, on-demand contraception and to processes for preparing this pharmaceutical composition. The latter comprises 2H-indazole as novel EP2 receptor antagonists in combination with COX inhibitors. The invention furthermore provides a method for non-hormonal female-controlled on-demand contraception where a pharmaceutical composition comprising EP2 receptor antagonists in combination with COX inhibitors is taken on demand prior to expected sexual intercourse.

  这项发明涉及一种用于非激素、按需避孕的药物组合物，以及制备该药物组合物的方法。后者包括2H-吲哚唑作为新型EP2受体拮抗剂，与COX抑制剂结合使用。该发明还提供了一种非激素女性控制的按需避孕方法，其中在预期性交前按需服用含有EP2受体拮抗剂与COX抑制剂的药物组合物。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR TREATMENT OF HEPATITIS C<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2014205592A1

  公开（公告）日：2014-12-31

  Compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system are disclosed.

  具有式（I）的化合物可用作乙型肝炎病毒（HCV）NS5B聚合酶抑制剂，公开了这类化合物的合成以及将这类化合物用于抑制HCV NS5B聚合酶活性、治疗或预防HCV感染以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生的用途。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF HEPATITIS C<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS MÉTHODES D'UTILISATION POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2014209729A1

  公开（公告）日：2014-12-31

  The present invention relates to compounds of formula I that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.(I)

  本发明涉及一种公式I的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5B聚合酶抑制剂，以及该化合物的合成，以及利用该化合物抑制HCV NS5B聚合酶活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• Inhibition of inflammation using interleukin-1beta-converting enzyme (ICE)/CED-3 family inhibitors
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US20020123522A1

  公开（公告）日：2002-09-05

  The present invention provides methods for expanding and increasing survival of hematopoietic cell populations, for prolonging viability of an organ for transplantation, and enhancing bioproduction, using interleukin-1&bgr;-converting enzyme (ICE)/CED-3 family inhibitors. Exemplary compounds useful in the methods of the invention are provided herein.

  本发明提供了一种使用白细胞介素-1β转化酶（ICE）/CED-3家族抑制剂来扩展和增加造血细胞群体的存活、延长移植器官的存活能力和增强生物生产的方法。本发明中提供了可用于该方法中的典型化合物。