tert-butyl (3-iodo-1H-indazol-5-yl)carbamate | 1338795-64-4

• 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: tert-butyl (3-iodo-1H-indazol-5-yl)carbamate
• 英文别名: tert-butyl 3-iodo-1H-indazol-5-ylcarbamate；tert-butyl N-(3-iodo-2H-indazol-5-yl)carbamate
• CAS: 1338795-64-4
• 化学式: C₁₂H₁₄IN₃O₂
• 分子量: 359.167
• InChiKey: KBCSQTARTCMKGN-UHFFFAOYSA-N

物化性质

• 沸点：
  425.6±25.0 °C(Predicted)
• 密度：
  1.741±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-iodo-1H-indazol-5-yl)carbamate 在 potassium fluoride 、 四(三苯基膦)钯 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 tert-butyl 4-phenyl-4-(3-(3-sulfamoylphenyl)-1H-indazol-5-ylcarbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

  摘要：

  TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50=3.6nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.

  DOI：

  10.1016/j.bmc.2014.06.027
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碘 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 tert-butyl (3-iodo-1H-indazol-5-yl)carbamate
  参考文献：
  名称：

  [EN] KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME
  [FR] INHIBITEURS DE KINASES ET PROCÉDÉ DE TRAITEMENT DU CANCER UTILISANT CEUX-CI

  摘要：

  本教学提供了一种由结构式(I)表示的化合物，或其药用可接受的盐。还描述了一种药物组合物及其使用方法。

  公开号：

  WO2011123937A1

文献信息

• [EN] INDAZOLE COMPOUNDS AS KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME<br/>[FR] COMPOSÉS INDAZOLE UTILISÉS COMME INHIBITEURS DE KINASE ET MÉTHODE DE TRAITEMENT DU CANCER AVEC LESDITS COMPOSÉS
  申请人：UNIV HEALTH NETWORK

  公开号：WO2013053051A1

  公开（公告）日：2013-04-18

  The present teaching provide indazole compounds represented by Structural Formulae (I) or (I') or a pharmaceutically acceptable salt thereof. Also described are pharmaceutical compositions and methods of use thereof as protein kinase inhibitors, such as TTK protein kinase, polo-like kinase 4 (PLK4) and Aurora kinases having anticancer activity against breast cancer cells, colon cancer cells, and ovarian cancer cells.

  本教学提供了由结构式（I）或（I'）表示的吲唑化合物或其药用可接受的盐。还描述了这些药物组合物及其用作蛋白激酶抑制剂的方法，如对乳腺癌细胞、结肠癌细胞和卵巢癌细胞具有抗癌活性的TTK蛋白激酶、极化样激酶4（PLK4）和极化激酶。
• Suzuki-Type Cross-Coupling Reaction of Unprotected 3-Iodoindazoles with Pinacol Vinyl Boronate: An Expeditive C-3 Vinylation of Indazoles under Microwave Irradiation
  作者：Gonzalo Vera、Benjamín Diethelm、Claudio Terraza、Gonzalo Recabarren-Gajardo

  DOI：10.3390/molecules23082051

  日期：——

  C-5 substituted 3-iodoindazole derivatives. In all cases, the C-3 vinylated derivative was the only isolated product. This methodology allows access to 3-vinylated indazoles selectively and directly without the need of N-protection. 3-Vinylindazoles could be interesting synthetic intermediates allowing access to biologically active molecules.

  本文中，我们报告了微波辐射下未保护的3-碘吲唑的便捷C-3乙烯基化。通过这种方法合成了十种C-5取代的3-乙烯基吲唑衍生物，其中九种是新颖的，从C-5取代的3-碘吲唑衍生物开始，以中等至优异的产率进行。在所有情况下，C-3乙烯基化衍生物都是唯一的分离产物。这种方法可以选择性地和直接地获得3-乙烯基化的吲唑，而无需N-保护。3-乙烯基吲唑可能是有趣的合成中间体，可以接触生物活性分子。
• INDAZOLE COMPOUNDS AS KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME
  申请人：University Health Network

  公开号：US20140371202A1

  公开（公告）日：2014-12-18

  The present teaching provide indazole compounds represented by Structural Formulae (I) or (I′) or a pharmaceutically acceptable salt thereof. Also described are pharmaceutical compositions and methods of use thereof as protein kinase inhibitors, such as TTK protein kinase, polo-like kinase 4 (PLK4) and Aurora kinases having anticancer activity against breast cancer cells, colon cancer cells, and ovarian cancer cells.

  本教学提供由结构式（I）或（I'）所代表的吲唑化合物或其药学上可接受的盐。还描述了制备药物组合物和使用方法，作为蛋白激酶抑制剂，例如TTK蛋白激酶，极化样激酶4（PLK4）和极化激酶，对乳腺癌细胞，结肠癌细胞和卵巢癌细胞具有抗癌活性。
• KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME
  申请人：UNIVERISTY HEALTH NETWORKS

  公开号：US20140051679A1

  公开（公告）日：2014-02-20

  The present teachings provide a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are pharmaceutical compositions and methods of use thereof.

  本文提供了一种由结构式（I）表示的化合物，或其药学上可接受的盐。还描述了这些药物组合物的制备方法和使用方法。
• LRRK2 억제 활성을 갖는 인다졸 화합물
  申请人：주식회사 스탠다임

  公开号：KR20230118694A

  公开（公告）日：2023-08-11

  본 발명은 화학식 1의 신규한 류신-풍부 반복 키나제 2(leucine-rich repeat kinase 2: LRRK2) 억제제, 이를 포함하는 LRRK2에 의해 매개되거나 이와 관련된 질병 또는 질환의 예방 또는 치료용 약학적 조성물, 및 이를 이용한 질병의 치료 및 예방 방법에 관한 것이다. 본 발명에 따른 화합물은 LRRK2 저해 활성이 우수하여 LRRK2에 의해 매개되거나 이와 관련된 질병 또는 질환(예컨대, 파킨슨병)의 예방 또는 치료에 효과적으로 사용될 수 있다.

  本发明涉及化学式1所示的一种新型富含亮氨酸的重复蛋白 kinase 2 (LRRK2)抑制剂，该抑制剂可用于制备预防或治疗由LRRK2介导或与其相关的疾病或病症(例如帕金森病)的药物组合物，以及利用该抑制剂进行疾病治疗和预防的方法。 根据本发明的化合物具有优异的 LRRK2 抑制活性，因此可有效地用于预防或治疗由 LRRK2 介导或与其相关的疾病或病症(例如帕金森病)。