2-(2,3-difluorophenyl)-1H-imidazole | 1268385-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,3-difluorophenyl)-1H-imidazole
• CAS: 1268385-42-7
• 化学式: C₉H₆F₂N₂
• mdl: MFCD08668730
• 分子量: 180.157
• InChiKey: LTJCSZRCZISYNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,3-difluorophenyl)-1H-imidazole 在 Pt(5%)Bi(5%)/C 、 氢溴酸 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 反应 15.17h， 生成 methyl {3-[4-cyclopropyl-2-(trifluoromethyl)phenyl]-5-isoxazolyl}[2-(2,3-difluorophenyl)-5H-imidazo[4,5-d]pyridazin-5-yl]acetate
  参考文献：
  名称：

  Synthesis of HCV Replicase Inhibitors: Base-Catalyzed Synthesis of Protected α-Hydrazino Esters and Selective Aerobic Oxidation with Catalytic Pt/Bi/C for Synthesis of Imidazole-4,5-dicarbaldehyde

  摘要：

  A robust convergent synthesis of the prodrugs of HCV replicase inhibitors 1-5 is described. The central 5H-imidazo[4,S-d]pyridazine core was formed from acid-catalyzed cyclocondensation of an imidazole-4,5-dicarbaldehyde (20) and a alpha-hydrazino ester, generated in situ from the bis-BOC-protected precursors 25 and 33. The acidic conditions not only released the otherwise unstable alpha-hydrazino esters but also were the key to avoid facile decarboxylation to the parent drugs from the carboxylic ester prodrugs 1-5. The bis-BOC alpha-hydrazino esters 25 and 33 were prepared by addition of ester enolates (from 23 and 32) to di-tert-butyl azodicarboxylate via catalysis with mild inorganic bases, such as Li2CO3. A selective aerobic oxidation with catalytic 5% Pt-Bi/C in aqueous KOH was developed to provide the dicarbaldehyde 20 from the diol 27.

  DOI：

  10.1021/jo4014595
• 作为产物：
  描述：

  草酸醛 、 2,3-二氟苯甲醛 在 ammonium acetate 作用下， 以 水 、 异丙醇 为溶剂， 以87%的产率得到2-(2,3-difluorophenyl)-1H-imidazole
  参考文献：
  名称：

  Imidazopyridazine Compounds for Treating Viral Infections

  摘要：

  揭示了化合物和Formula (I)的组成，其药用可接受的盐和溶剂，以及它们的制备和用于治疗至少部分由黄病毒科病毒介导的病毒感染的用途。

  公开号：

  US20110052534A1

文献信息

• [EN] 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE COMPOUNDS FOR THE TREATMENT OF TUBERCULOSIS<br/>[FR] COMPOSES 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2005042542A1

  公开（公告）日：2005-05-12

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1)in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and -(CH2)nR2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30)and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下一般式表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物：(1)在上述式(1)中，R1代表氢原子或C1-C6烷基，n代表0至6的整数，R1和-(CH2)nR2可以与下面的式(30)一起形成一个螺环，与相邻的碳原子一起（在下面的式中，RRR代表可能在哌啶环上具有取代基的哌啶基），(30)和R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似物。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型耐酸细菌具有出色的杀菌作用。
• Imidazo[4,5-d]Pyridazine Compounds For Treating Viral Infections
  申请人：Leivers Martin

  公开号：US20110053892A1

  公开（公告）日：2011-03-03

  Disclosed are compounds and compositions of Formula (I), pharmaceutically acceptable salts and solvates thereof, and their preparation and uses for treating viral infections mediated at least in part by a virus in the Flaviviridae family of viruses:

  本发明涉及公式(I)的化合物和组合物，其药学上可接受的盐和溶剂化物，以及它们的制备和用于治疗由Flaviviridae病毒家族中的病毒至少部分介导的病毒感染的用途：
• INHIBITORS OF POLO-LIKE KINASE
  申请人：Galemmo Robert A.

  公开号：US20110207716A1

  公开（公告）日：2011-08-25

  The present invention provides compounds having a structure according to Formula (I): or a salt or solvate thereof, wherein ring A, E 1 , E 2 , R 1 , R 2 , R 3 and R 4 are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.

  本发明提供了具有以下结构的化合物（I）的盐或溶剂，其中环A、E1、E2、R1、R2、R3和R4在此定义。本发明还提供了包括本发明化合物的制药组合物以及使用本发明化合物和组合物的方法，例如在治疗和预防各种疾病，如帕金森病方面的应用。
• Inhibitors of Polo-Like Kinase
  申请人：Galemmo, JR. Robert A.

  公开号：US20120115848A1

  公开（公告）日：2012-05-10

  The present invention provides compounds having a structure according to Formula (I): or a salt or solvate thereof, wherein ring A, U 1 , U 2 , U 3 , R 2 , R 3 and R 4 are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.

  本发明提供具有以下结构的化合物（I）或其盐或溶剂化物，其中环A、U1、U2、U3、R2、R3和R4如本文所定义。该发明还提供包括该发明化合物的制药组合物以及制备和使用该发明化合物和组合物的方法，例如用于治疗和预防各种疾病，如帕金森病。
• EP1534074A4
  申请人：——

  公开号：EP1534074A4

  公开（公告）日：2008-01-09