6-(4-methoxyphenyl)-N-phenylquinazolin-4-amine | 1445580-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-(4-methoxyphenyl)-N-phenylquinazolin-4-amine
• CAS: 1445580-87-9
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: GFJRSXXZMZUHTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-iodo-N-phenyl-4-quinazolin-amine 、 4-甲氧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以16%的产率得到6-(4-methoxyphenyl)-N-phenylquinazolin-4-amine
  参考文献：
  名称：

  Emission Tuning of Fluorescent Kinase Inhibitors: Conjugation Length and Substituent Effects

  摘要：

  Fluorescent N-phenyl-4-aminoquinazoline probes targeting the ATP-binding pocket of the ERBB family of receptor tyrosine kinases are reported. Extension of the aromatic quinazoline core with fluorophore "arms" through substitution at the 6- position of the quinazoline core with phenyl, styryl, and phenylbutadienyl moieties was predicted by means of TD-DFT calculations to produce probes with tunable photoexcitation energies and excited states possessing charge-transfer character. Optical spectroscopy identified several synthesized probes that are nonemissive in aqueous solutions and exhibit emission enhancements in solvents of low polarity, suggesting good performance as turn-on fluorophores. Ligand-induced ERBB2 phosphorylation assays demonstrate that despite chemical modification to the quinazoline core these probes still function as ERBB2 inhibitors in MCF7 cells. Two probes were found to exhibit ERBB2-induced fluorescence, demonstrating the utility of these probes as turn-on, fluoroescent kinase inhibitors.

  DOI：

  10.1021/jo500520x

文献信息

• QUINAZOLINE COMPOUNDS AS KINASE INHIBITORS
  申请人：Huang Jiann-Jyh

  公开号：US20130165458A1

  公开（公告）日：2013-06-27

  A compound for treating protein kinase-related disease or disorder having a structure of formula (A): wherein X is N or CH; Y is NH, O, or CH 2 ; Z is an aryl or a heteroaryl; and R 1 , R 2 , R 3 , and R 4 are independently H, halo, nitro, cyano, aryl, heteroaryl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, —OR a , —C(O)R a , —C(O)NR a R b , —NR a C(O)R b , —NR a R b , —S(O) 2 R a , —S(O) 2 NR a R b , —NR a S(O) 2 R b , —N═CR a R b , or —NR a C(O)NHR b , wherein each of R a and R b , independently, is H, alkyl, alkenyl, alkynyl, aryl, aryloxy, alkoxy, hydroxy, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, or heterocycloalkenyl, or R a and R b , together with the nitrogen atom to which they are bonded, form heteroaryl, heterocycloalkyl, or heterocycloalkenyl; or R 3 and R 4 are as defined above, and R 1 and R 2 together with the carbons, to which they are attached, form a heterocycloalkenyl or heteroaryl.

  一种用于治疗蛋白激酶相关疾病或紊乱的化合物，其结构具有如下式（A）：其中X为N或CH；Y为NH、O或CH2；Z为芳基或杂环芳基；R1、R2、R3和R4独立地为H、卤素、硝基、氰基、芳基、杂环芳基、烷基、烯基、炔基、环烷基、杂环环烷基、环烯基、杂环环烯基、—ORa、—C（O）Ra、—C（O）NRaRb、—NRaC（O）Rb、—NRaRb、—S（O）2Ra、—S（O）2NRaRb、—NRaS（O）2Rb、—N═CRaRb或—NRaC（O）NHRb，其中Ra和Rb各自独立地为H、烷基、烯基、炔基、芳基、芳氧基、烷氧基、羟基、杂环芳基、环烷基、杂环环烷基、环烯基或杂环环烯基，或者Ra和Rb与它们结合的氮原子一起形成杂环芳基、杂环环烷基或杂环环烯基；或者R3和R4如上所定义，R1和R2与它们连接的碳一起形成杂环环烯基或杂环芳基。
• US8785459B2
  申请人：——

  公开号：US8785459B2

  公开（公告）日：2014-07-22