N-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide | 1010120-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: N-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
• CAS: 1010120-53-2
• 化学式: C₈H₇BrN₄O
• 分子量: 255.074
• InChiKey: FOLUAZVPAYIBKB-UHFFFAOYSA-N

物化性质

• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 potassium acetate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以100%的产率得到N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
  参考文献：
  名称：

  [EN] AMINO TRIAZOLES AS PI3K INHIBITORS
  [FR] AMINOTRIAZOLES COMME INHIBITEURS DE P13K

  摘要：

  公开号：

  WO2009068482A8
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 盐酸羟胺 、 氨 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 N-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
  参考文献：
  名称：

  SAR studies around a series of triazolopyridines as potent and selective PI3Kγ inhibitors

  摘要：

  Herein we describe the SAR of a novel series of 6-aryl-2-amino-triazolopyridines as potent and selective PI3K gamma inhibitors. The 6-aryl-triazolopyridine core was identified by chemoproteomic screening of a kinase focused library. Rapid chemical expansion around a bi-functional core identified the key features required for PI3K gamma activity and selectivity. The series was optimized to afford 43 (CZC19945), a potent PI3K gamma inhibitor with high oral bioavailability and selectivity over PI3K alpha and PI3K delta. Modification to the core afforded 53 (CZC24832) which showed increased selectivity over the entire kinome in particular over PI3K beta. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.049

文献信息

• Combination of 2-methoxy-3-phenylsulfonylaminobenzamide and 2-aminobenzothiazole to discover novel anticancer agents
  作者：Huan Li、Xiao-Meng Wang、Juan Wang、Teng Shao、Yi-Ping Li、Qi-Bing Mei、She-Min Lu、San-Qi Zhang

  DOI：10.1016/j.bmc.2014.04.064

  日期：2014.7

  antiproliferative activity was examined for its effect on the AKT and p-AKT473. The anticancer effect of 1g was evaluated in established nude mice HCT-116 xenograft model. The results suggested that compound 1g can block PI3K/AKT/mTOR pathway and significantly inhibit tumor growth. These findings strongly support our assumption that the fragment of benzamide can replace the pyridine ring in some PI3K and mTOR dual

  已经提出了2-取代的-3-磺酰基氨基苯甲酰胺的片段来代替PI3K和mTOR双重抑制剂中的2-取代的-3-磺酰基氨基吡啶的片段，以设计基于生物等排体的新型抗癌剂。2-取代的3-磺酰基氨基苯甲酰胺的片段与2-氨基苯并噻唑或2-氨基噻唑并[5,4- b ]吡啶或2-氨基[1,2,4]三唑并[1,5-]的片段的组合一个]吡啶制备抗癌剂的新颖结构。结果，合成并表征了十九种目标化合物。通过MTT测定法评估了它们在体外对四种人类癌细胞系的体外抗增殖活性，所述细胞系包括HCT-116，A549，MCF-7和U-87 MG。初步讨论了目标化合物的SAR。化合物1g研究了具有强抗增殖活性的化合物对AKT和p-AKT 473的作用。在已建立的裸鼠HCT-116异种移植模型中评估了1g的抗癌作用。结果表明，化合物1g可以阻断PI3K / AKT / mTOR通路，并显着抑制肿瘤的生长。这些发现强烈支持我们的假设，
• TRIAZOLE DERIVATIVES AS KINASE INHIBITORS
  申请人：Wilson Francis

  公开号：US20100227800A1

  公开（公告）日：2010-09-09

  The invention relates to compounds of formula (I); wherein X and R 1 to R 5 have the meaning as cited in the description and the claims. Said compounds are useful as protein kinase inhibitors, especially inhibitors of Itk or PI3K, for the treatment or prophylaxis of immunological, inflammatory or allergic disorders. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the production of and use as medicaments.

  本发明涉及式(I)的化合物；其中X和R1至R5的含义如所述及权利要求中所述。所述化合物可用作蛋白激酶抑制剂，特别是Itk或PI3K的抑制剂，用于治疗或预防免疫、炎症或过敏性疾病。本发明还涉及包括所述化合物的制药组合物，以及制备这些化合物的方法以及作为药物的生产和使用。
• Amino triazoles as PI3K inhibitors
  申请人：Ramsden Nigel

  公开号：US08865699B2

  公开（公告）日：2014-10-21

  The invention relates to compounds of formula (I) wherein X, T1 and R1 to R3 have the meaning as cited in the description and the claims. Said compounds are useful as protein kinase inhibitors, especially inhibitors of PI3K, for the treatment or prophylaxis of immunological, inflammatory, autoimmune, or allergic disorders. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the production of and use as medicaments.

  该发明涉及公式（I）的化合物，其中X、T1和R1至R3的含义如说明书和权利要求书所述。所述化合物可用作蛋白激酶抑制剂，特别是PI3K的抑制剂，用于治疗或预防免疫、炎症、自身免疫或过敏性疾病。该发明还涉及包括所述化合物的制药组合物，以及制备此类化合物的方法以及作为药物的生产和使用。
• Triazole derivatives as kinase inhibitors
  申请人：Wilson Francis

  公开号：US08883820B2

  公开（公告）日：2014-11-11

  The invention relates to compounds of formula (I); wherein X and R1 to R5 have the meaning as cited in the description and the claims. Said compounds are useful as protein kinase inhibitors, especially inhibitors of Itk or PI3K, for the treatment or prophylaxis of immunological, inflammatory or allergic disorders. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the production of and use as medicaments.

  本发明涉及公式(I)的化合物；其中X和R1到R5的含义如说明书和权利要求所述。所述化合物可用作蛋白激酶抑制剂，特别是Itk或PI3K的抑制剂，用于治疗或预防免疫、炎症或过敏性疾病。本发明还涉及包括所述化合物的制药组合物，以及制备此类化合物的方法以及其作为药物的生产和使用。
• AMINO TRIAZOLES AS PI3K INHIBITORS
  申请人：Ramsden Nigel

  公开号：US20110021497A1

  公开（公告）日：2011-01-27

  The invention relates to compounds of formula (I) wherein X, T 1 and R 1 to R 3 have the meaning as cited in the description and the claims. Said compounds are useful as protein kinase inhibitors, especially inhibitors of PI3K, for the treatment or prophylaxis of immunological, inflammatory, autoimmune, or allergic disorders. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the production of and use as medicaments.

  本发明涉及式(I)的化合物，其中X、T1和R1至R3具有所述说明书和权利要求中所述的含义。所述化合物可用作蛋白激酶抑制剂，特别是PI3K的抑制剂，用于治疗或预防免疫、炎症、自身免疫或过敏性疾病。本发明还涉及包括所述化合物的制药组合物，以及制备此类化合物以及作为药物的生产和使用。