1-(4-fluorophenyl)-6,7-dihydro-5H-indazol-4-one | 37901-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-fluorophenyl)-6,7-dihydro-5H-indazol-4-one
• 英文别名: 1-(4-fluorophenyl)-1,5,6,7-tetrahydroindazol-4-one
• CAS: 37901-73-8
• 化学式: C₁₃H₁₁FN₂O
• mdl: MFCD07469797
• 分子量: 230.242
• InChiKey: UDCUZAJVQJQLLW-UHFFFAOYSA-N

物化性质

• 沸点：
  372.5±30.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-6,7-dihydro-5H-indazol-4-one 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-1H-indazol-4-amine
  参考文献：
  名称：

  Identification, Synthesis, and Pharmacological Evaluation of Tetrahydroindazole Based Ligands as Novel Antituberculosis Agents

  摘要：

  The resurgence Of tuberculosis (TB), the incidence of drug-resistant strains of Mycobacterium tuberculosis (MTB), and the coinfection between TB and HIV have led to serious infections, high mortality, and it global health threat, resulting in the urgent search for new classes of antimycobacterial agents. Herein, we report the identification of a novel class of tetrahydroindazole based compounds as potent and unique inhibitors of MTB. Compounds 6a, 6m, and 6q exhibited activity in the low micromolar range against replicating Mycobacterium tuberculosis (R-TB) phenotype, with minimum inhibitory concentrations (MICs) of 1.7, 1.9, and 1.9 mu M, respectively, while showing no toxicity to Vero Ccells, Moreover, studies aimed to assess the in vitro metabolic stability of 6a and 6m in mouse liver microsomes and in vivo pharmacokinetic profiles in plasma levels gave satisfactory results. This research suggests that tetrahydroindazole based anti-TB compounds can serve its a promising lead scaffold in developing new drugs to combat tuberculosis infections.

  DOI：

  10.1021/jm901235p
• 作为产物：
  描述：

  1,3-环己二酮 在 盐酸 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(4-fluorophenyl)-6,7-dihydro-5H-indazol-4-one
  参考文献：
  名称：

  A novel synthetic approach to 4-acetamido-1-arylindazoles via Semmler–Wolff rearrangement of 1-aryl-6,7-dihydro-5H-indazol-4-one oxime

  摘要：

  A simple and efficient procedure for the syntheses of 4-acetamido-1-arylindazoles from corresponding 1-aryl-6,7-dihydro-5H-indazol-4-one oximes by Semmler-Wolff aromatization using acetic anhydride and sodium iodide is reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.058

文献信息

• [EN] NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES<br/>[FR] NOUVEAUX CATALYSEURS AU RUTHÉNIUM ET LEUR UTILISATION POUR LA RÉDUCTION ASYMÉTRIQUE DE CÉTONES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015002769A1

  公开（公告）日：2015-01-08

  Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R1 and the moiety L ∩ L are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.

  揭示了一种新型钌化合物的结构式(Ia)和(Ib)：其中R1和基团L ∩ L在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行不对称加氢和酮的转移加氢的方法，具有高反应性和优异选择性。
• [EN] PYRAZOLOPIPERIDINE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS DE PYRAZOLOPIPÉRIDINE EN TANT QU'ANTAGONISTES DE RÉCEPTEUR CCR1
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012087782A1

  公开（公告）日：2012-06-28

  Disclosed are compounds of the formula (I), useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of CCR1 including autoimmune diseases, such as rheumatoid arthritis and multiple sclerosis. Also disclosed are methods of making and methods of using same.

  揭示了一种公式（I）的化合物，可用于治疗多种通过CCR1活性介导或维持的疾病和紊乱，包括自身免疫性疾病，如类风湿性关节炎和多发性硬化症。还公开了制备方法和使用方法。
• NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES
  申请人：HADDAD Nizar

  公开号：US20150005500A1

  公开（公告）日：2015-01-01

  Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R 1 and the moiety are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.

  本发明揭示了一种新型钌化合物的化学式(Ia)和(Ib)：其中R1和该基团在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行酮类的不对称氢化和转移氢化的方法，具有高反应性和优异选择性。
• Amine-Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones
  作者：Sonia Rodríguez、Bo Qu、Keith R. Fandrick、Frederic Buono、Nizar Haddad、Yibo Xu、Melissa A. Herbage、Xingzhong Zeng、Shengli Ma、Nelu Grinberg、Heewon Lee、Zhengxu S. Han、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1002/adsc.201300727

  日期：2014.2.10

  AbstractA series of efficient ruthenium catalysts has been developed for the asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and selectivities. The new chiral bisdihydrobenzooxaphosphole (BIBOP)/diamine‐ruthenium complexes catalyzed the enantioselective hydrogenation of substrates such as aryl and heteroaryl cyclic and alkyl ketones with substrate/catalyst (S/C) ratios of up to 100,000. The opposite sense of enantioselectivity can be obtained by proper selection of a diamine with a given chirality of the phosphine. The usefulness of the new system has been demonstrated in the asymmetric hydrogenation of a complex synthetic intermediate towards cholesteryl ester transfer protein (CETP) inhibitors at S/C 20,000 on large‐scale operation.magnified image
• PYRAZOLOPIPERIDINE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2655371B1

  公开（公告）日：2015-02-25