5-bromo-N3-(2-methoxybenzyl)-pyrazine-2,3-diamine | 639450-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-N3-(2-methoxybenzyl)-pyrazine-2,3-diamine
• 英文别名: 5-bromo-3-N-[(2-methoxyphenyl)methyl]pyrazine-2,3-diamine
• CAS: 639450-08-1
• 化学式: C₁₂H₁₃BrN₄O
• 分子量: 309.165
• InChiKey: UOKFWTUBIWJOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-bromo-N3-(2-methoxybenzyl)-pyrazine-2,3-diamine 在 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 6-(4-hydroxyphenyl)-1-(2-methoxybenzyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one
  参考文献：
  名称：

  Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors

  摘要：

  We report here the discovery of a novel series of selective mTOR kinase inhibitors. A series of imidazo[ 4,5-b]pyrazin-2-ones, represented by screening hit 1, was developed into lead compounds with excellent mTOR potency and exquisite kinase selectivity. Potent compounds from this series show >1000-fold selectivity over the related PI3K alpha lipid kinase. Further, compounds such as 2 achieve mTOR pathway inhibition, blocking both mTORC1 and mTORC2 signaling, in PC3 cancer cells as measured by inhibition of pS6 and pAkt (S473). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.035
• 作为产物：
  描述：

  邻甲氧基苄胺 、 2-氨基-3,5-二溴吡嗪 反应 20.0h， 生成 5-bromo-N3-(2-methoxybenzyl)-pyrazine-2,3-diamine
  参考文献：
  名称：

  Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors

  摘要：

  We report here the discovery of a novel series of selective mTOR kinase inhibitors. A series of imidazo[ 4,5-b]pyrazin-2-ones, represented by screening hit 1, was developed into lead compounds with excellent mTOR potency and exquisite kinase selectivity. Potent compounds from this series show >1000-fold selectivity over the related PI3K alpha lipid kinase. Further, compounds such as 2 achieve mTOR pathway inhibition, blocking both mTORC1 and mTORC2 signaling, in PC3 cancer cells as measured by inhibition of pS6 and pAkt (S473). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.035

文献信息

• Certain amino-substituted monocycles as kinase modulators
  申请人：——

  公开号：US20040053927A1

  公开（公告）日：2004-03-18

  A composition comprises a compound of Formula 1: 1 a pharmaceutically acceptable salt, hydrate, solvate, crystal form, diastereomer, prodrug, or mixture thereof, wherein W is a nitrogen-substituted 5- or 6-membered monocyclic ring. The compounds are of utility as modulators of kinase activity.

  该组合物包括公式1的化合物：1a，其为药学上可接受的盐、水合物、溶剂物、晶体形式、对映体、前药或其混合物，其中W为氮取代的5-或6-成员的单环环。该化合物具有调节激酶活性的功效。
• [EN] CERTAIN AMINO-SUBSTITUTED MONOCYCLES AS KINASE MODULATORS<br/>[FR] UTILISATION DE CERTAINS MONOCYCLES A SUBSTITUTION AMINO EN TANT QUE MODULATEURS DE L'ACTIVITE DES KINASES
  申请人：CELLULAR GENOMICS INC

  公开号：WO2004000318A3

  公开（公告）日：2004-04-08
• US7015227B2
  申请人：——

  公开号：US7015227B2

  公开（公告）日：2006-03-21