6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid | 1290056-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid
• 英文别名: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthoic acid；6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-napthoic acid；6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid
• CAS: 1290056-68-6
• 化学式: C₁₇H₁₉BO₄
• 分子量: 298.146
• InChiKey: PVUWMHABPMJUDP-UHFFFAOYSA-N

物化性质

• 沸点：
  481.8±18.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.25h， 生成 6-(3-amino-1H-indazol-4-yl)-N-(5-methylisoxazol-3-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
• 作为产物：
  描述：

  6-羟基-1-萘甲酸 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 氯化亚砜 、 lithium hydroxide monohydrate 、 水 、 potassium acetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-1-carboxylic acid
  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

• COFERONS AND METHODS OF MAKING AND USING THEM
  申请人：Barany Francis

  公开号：US20120295874A1

  公开（公告）日：2012-11-22

  The present invention is directed to a monomer useful in preparing therapeutic compounds. The monomer includes one or more pharmacophores which potentially binds to a target molecule with a dissociation constant of less than 300 μM and a linker element connected to the pharmacophore. The linker element has a molecular weight less than 500 daltons, is connected, directly or indirectly through a connector, to the pharmacophore.

  本发明涉及一种用于制备治疗性化合物的单体。该单体包括一个或多个可与目标分子结合的药效团，其解离常数小于300微摩尔，以及与药效团连接的连接元素。所述连接元素的分子量小于500道尔顿，通过直接连接或通过连接器间接与药效团相连。
• [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。
• NAPHTHYLAMIDE COMPOUND, PREPARATION METHOD AND USE THEREOF
  申请人：Shanghai Institute Of Materia Medica Chinese Academy of Sciences

  公开号：EP3112351B1

  公开（公告）日：2022-03-30