N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthamide | 1571111-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthamide
• 英文别名: 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid cyclopropylamide；N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthalenecarboxamide；N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxamide
• CAS: 1571111-80-2
• 化学式: C₂₀H₂₄BNO₃
• 分子量: 337.226
• InChiKey: AWXIIMWTYLGGOE-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  553.1±23.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基-4-碘-吲唑 、 N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthamide 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 2.0h， 以68%的产率得到6-(3-amino-1H-indazol-4-yl)-N-cyclopropyl-1-naphthamide
  参考文献：
  名称：

  Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors

  摘要：

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.

  DOI：

  10.1021/ml5000417
• 作为产物：
  描述：

  6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.25h， 生成 N-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthamide
  参考文献：
  名称：

  Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors

  摘要：

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.

  DOI：

  10.1021/ml5000417

文献信息

• [EN] 6-AMINO-7-BICYCLO-7-DEAZA-PURINE DERIVATIVES AS PROTEIN KINASE INHIBITORS<br/>[FR] DÉRIVÉS 6-AMINO -7-BICYCLO -7-DÉAZAPURINE UTILES EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2016075224A1

  公开（公告）日：2016-05-19

  The present invention relates to 6-amino-7-bicyclo-7-deaza-purine derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity, in particular RET family kinases. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing pharmaceutical compositions containing these compounds.

  本发明涉及6-氨基-7-双环-7-去氮嘌呤衍生物，其调节蛋白激酶的活性，因此在治疗由失调的蛋白激酶活性引起的疾病，特别是RET家族激酶方面具有用途。本发明还提供了制备这些化合物的方法，包含这些化合物的药物组合物，以及利用含有这些化合物的药物组合物治疗疾病的方法。