3-(acetylamino)indazole | 70997-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 3-(acetylamino)indazole
• 英文别名: 3-acetamidoindazole；N-(1(2)H-indazol-3-yl)-acetamide；3-Acetylaminoindazol；N-(1H-indazol-3-yl)acetamide
• CAS: 70997-35-2
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: VCFLLXDSOODEGV-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C(Solvent: Ethanol ; Ethyl acetate)
• 沸点：
  482.7±18.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(acetylamino)indazole 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 生成 1,N-(2-chloropyrimidin-4-yl)-3-(N-ethyl-N-methylamino)-1H-indazole
  参考文献：
  名称：

  [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE
  [FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR

  摘要：

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。

  公开号：

  WO2017120429A1
• 作为产物：
  描述：

  N-(1-benzoylindazol-3-yl)acetamide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以67%的产率得到3-(acetylamino)indazole
  参考文献：
  名称：

  Korbonits, Dezsoe; Kolonits, Pal, Acta Chimica Hungarica, 1990, vol. 127, # 6, p. 795 - 802

  摘要：

  DOI：

文献信息

• Synthetic Studies toward 3-(Acylamino)-1H-indazoles and Development of a One-Pot, Microwave-Assisted, Oxadiazole Condensation/Boulton-Katritzky Rearrangement
  作者：Gregory Ott、Andrew Anzalone

  DOI：10.1055/s-0031-1289893

  日期：2011.12

  devised that allows access to rearrangement products in good to excellent isolated yields. Furthermore, we have developed a two-component, one-pot sequence using a microwave-assisted oxadiazole condensation/Boulton-Katritzky rearrangement to deliver 3-(acylamino)-1H-indazoles from simple esters and 2-amino-N-hydroxy-benzamidine Boulton-Katritzky rearrangement - indazole - microwave-assisted - oxadiazole

  对3-（2-氨基芳基）-1,2,4-恶二唑的Boulton-Katritzky重排的研究导致确定了控制重排以及选择底物竞争性热重排途径的其他电子因素。为了避免常规热转化序列的局限性，已设计出一种采用微波辐射的改进方案，该方案允许以良好的分离产率良好地获得重排产物。此外，我们已经开发了一种使用微波辅助的恶二唑缩合/ Boulton-Katritzky重排的两组分，一锅法序列，以从简单的酯和2-氨基-N-羟基-生成3-（酰基氨基）-1 H-吲唑。苯甲idine Boulton-Katritzky重排-吲唑-微波辅助-恶二唑缩合-取代基效应
• Aminoindazole derivatives and intermediates, preparation thereof, and pharmaceutical compositions thereof
  申请人：——

  公开号：US20040014802A1

  公开（公告）日：2004-01-22

  The present invention relates to the novel indazole derivatives of general formula (I): 1 in which: R is either O, S or NH; R3 is an alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, aryl, heterocycle, cycloalkyl, alkenyl, etc. radical; these radicals being optionally substituted with one or more substituents; R4, R5, R6 and R7 are chosen, independently of each other, from the following radicals: hydrogen, halogen, CN, NO 2 , NH 2 , OH, COOH, C(O)OR8, —O—C(O)R8, NR8R9, NHC(O)R8, C(O)NR8R9, NHC(S)R8, C(S)NR8R9, SR8, S(O)R8, SO 2 R8, NHSO 2 R8, SO 2 NR8R9, trifluoromethyl, trifluoromethoxy, alkyl, alkoxy, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycle, cycloalkyl, alkenyl, etc.; these radicals being optionally substituted with one or more substituents.

  本发明涉及一般式(I)的新型吲唑衍生物： 1 其中：R为O、S或NH；R3为烷基、芳基、芳基烷基、杂芳基、杂芳基烷基、芳基、杂环、环烷基、烯基等基团；这些基团可以选择性地被一个或多个取代基取代；R4、R5、R6和R7分别选择自以下基团：氢、卤素、CN、NO 2 、NH 2 、OH、COOH、C(O)OR8、—O—C(O)R8、NR8R9、NHC(O)R8、C(O)NR8R9、NHC(S)R8、C(S)NR8R9、SR8、S(O)R8、SO 2 R8、NHSO 2 R8、SO 2 NR8R9、三氟甲基、三氟甲氧基、烷基、烷氧基、芳基、芳基烷基、杂芳基、杂芳基烷基、杂环、环烷基、烯基等；这些基团可以选择性地被一个或多个取代基取代。
• Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them
  申请人：Martina Katia

  公开号：US20060106083A1

  公开（公告）日：2006-05-18

  Compounds which are indazole derivatives and pharmaceutically acceptable salts thereof, together with pharmaceutical compositions comprising them, as well as combinatorial libraries of indazole derivatives, as set forth in the specification, are disclosed; these compounds or compositions may be useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.

  这些是关于吲唑衍生物及其药用盐的化合物，以及包含它们的药物组合物，以及吲唑衍生物的组合化合物库的说明；这些化合物或组合物可能在治疗由改变的蛋白激酶活性引起和/或与之相关的疾病方面有用，如癌症、细胞增殖紊乱、阿尔茨海默病、病毒感染、自身免疫疾病和神经退行性疾病。
• Improved and expanded one-pot, two-component Boulton-Katritzky syntheses of N–N bond containing bicyclic heterocycles
  作者：Kyle W. Knouse、Laura E. Ator、Lauren E. Beausoleil、Zachary J. Hauseman、Rebecca L. Casaubon、Gregory R. Ott

  DOI：10.1016/j.tetlet.2016.11.092

  日期：2017.1

  two-component syntheses of bicyclic heterocycles containing a 3-N-acyl-3-amino-1,2-pyrazole motif from N′-hydroxy-carboxyamidines and acylbenzotriazoles have been developed. Importantly, this sequence obviates the need for hydrazine or N-aminating reagents to synthesize the key nitrogen–nitrogen (N–N) bond of these heterocycles, which is formed via Boulton-Katritzky rearrangement. A diverse array of pharmaceutically

  已经开发了改进的和扩展的由N'-羟基-羧am和酰基苯并三唑组成的包含3- N-酰基-3-氨基-1，2-吡唑基序的双环杂环的一锅两组分合成。重要的是，该序列无需使用肼或N-胺化试剂来合成这些杂环的关键氮-氮（N-N）键，该键是通过Boulton-Katritzky重排形成的。利用这种方法，无需任何特殊设备或条件，即可使用现成的试剂制备各种与药物相关的含N–N杂环。
• [EN] AMINOINDAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] DERIVES D'AMINOINDAZOLE AGISSANT COMME INHIBITEURS DE KINASE, METHODE D'OBTENTION ET COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2003097610A1

  公开（公告）日：2003-11-27

  Compounds which are indazole derivatives and pharmaceutically acceptable salts thereof together with pharmaceutical compositions comprising them, as well as combinatorial libraries of indazole derivatives, as set forth in the specification, are disclosed; these compounds or compositions may be useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.

  本发明公开了吲唑衍生物化合物及其药学上可接受的盐，以及包括它们的制药组合物，以及吲唑衍生物的组合化学库，这些化合物或组合物可能有用于治疗由于和/或与蛋白激酶活性改变相关的疾病，如癌症，细胞增殖性疾病，阿尔茨海默病，病毒感染，自身免疫疾病和神经退行性疾病。