3-(benzyloxy)-5-bromo-2-chloropyrazine | 1410164-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzyloxy)-5-bromo-2-chloropyrazine
• 英文别名: 3-(Benzyloxy)-5-bromo-2-chloropyrazine；5-bromo-2-chloro-3-phenylmethoxypyrazine
• CAS: 1410164-69-0
• 化学式: C₁₁H₈BrClN₂O
• 分子量: 299.554
• InChiKey: KOIZNXMVTYAMMV-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±37.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-5-bromo-2-chloropyrazine 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 16.33h， 生成 3-(benzyloxy)-2-(thiophen-3-yl)-5-(4-methoxyphenyl)pyrazine
  参考文献：
  名称：

  Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

  摘要：

  Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.039
• 作为产物：
  描述：

  2-氨基-3-苄氧基-5-溴吡嗪 在 copper(l) chloride 、 copper dichloride 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以41%的产率得到3-(benzyloxy)-5-bromo-2-chloropyrazine
  参考文献：
  名称：

  [EN] SHP2 INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE SHP2 ET LEURS UTILISATIONS

  摘要：

  公开了作为蛋白酪氨酸磷酸酶SHP2抑制剂的化合物1的化合物。还公开了包括化合物1的药物组合物、这些化合物的合成方法、使用这些化合物或含有这些化合物的组合物进行治疗与SHP2异常活性相关的疾病，如癌症的方法。

  公开号：

  WO2021061515A1

文献信息

• [EN] INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS<br/>[FR] COMPOSÉS INDOLIQUES UTILES EN TANT QUE MODULATEURS DU RÉCEPTEUR DES ANDROGÈNES
  申请人：NIDO BIOSCIENCES INC

  公开号：WO2022020342A1

  公开（公告）日：2022-01-27

  Provided herein are compounds of formula (V) that bind to BF3 of an androgen receptor (AR), which can modulate the AR for the treatment of Kennedy's disease.

  本文提供了一种公式（V）的化合物，它们与雄激素受体（AR）的BF3结合，可以调节AR以治疗肯尼迪病。
• [EN] SHP2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE SHP2 ET LEURS UTILISATIONS
  申请人：SYNBLIA THERAPEUTICS INC

  公开号：WO2021061515A1

  公开（公告）日：2021-04-01

  Compounds of Formula 1 as inhibitors of protein tyrosine phosphatase SHP2 are disclosed. The pharmaceutical compositions comprising compounds of Formula 1, methods of synthesis of these compounds, methods of treatment for diseases associated with the aberrant activity of SHP2 such as cancer using these compounds or compositions containing these compounds are also disclosed.

  公开了作为蛋白酪氨酸磷酸酶SHP2抑制剂的化合物1的化合物。还公开了包括化合物1的药物组合物、这些化合物的合成方法、使用这些化合物或含有这些化合物的组合物进行治疗与SHP2异常活性相关的疾病，如癌症的方法。
• SHP2 inhibitors and uses thereof
  申请人：SYNBLia Therapeutics, Inc.

  公开号：US10561655B2

  公开（公告）日：2020-02-18

  Compounds of Formula 1 as inhibitors of protein tyrosine phosphatase SHP2 are disclosed. The pharmaceutical compositions comprising compounds of Formula 1, methods of synthesis of these compounds, methods of treatment for diseases associated with the aberrant activity of SHP2 such as cancer using these compounds or compositions containing these compounds are also disclosed.

  本发明公开了作为蛋白酪氨酸磷酸酶 SHP2 抑制剂的式 1 化合物。还公开了包含式 1 化合物的药物组合物、合成这些化合物的方法、使用这些化合物或含有这些化合物的组合物治疗与 SHP2 活性异常有关的疾病（如癌症）的方法。
• SHP2 INHIBITORS AND USES THEREOF
  申请人：Synblia Therapeutics, Inc.

  公开号：EP3768664A1

  公开（公告）日：2021-01-27
• Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases
  作者：John J. Caldwell、Nicolas Veillard、Ian Collins

  DOI：10.1016/j.tet.2012.09.039

  日期：2012.11

  Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library. (c) 2012 Elsevier Ltd. All rights reserved.