4-(3-methoxybenzyloxy)-3-chlorobenzenamine | 937595-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-methoxybenzyloxy)-3-chlorobenzenamine
• 英文别名: 3-chloro-4-((3-methoxybenzyl)oxy)aniline；3-Chloro-4-[(3-methoxyphenyl)methoxy]aniline
• CAS: 937595-99-8
• 化学式: C₁₄H₁₄ClNO₂
• mdl: MFCD08699383
• 分子量: 263.724
• InChiKey: ZVSAHHDOHQWVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-methoxybenzyloxy)-3-chlorobenzenamine 、 4-((4-(4-chloroquinazolin-6-yl)phenyl)sulfonyl)morpholine hydrochloride 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以43.1%的产率得到N-[3-chloro-4-[(3-methoxyphenyl)methoxy]phenyl]-6-(4-morpholin-4-ylsulfonylphenyl)quinazolin-4-amine;hydrochloride
  参考文献：
  名称：

  Kinase Scaffold Repurposing for Neglected Disease Drug Discovery: Discovery of an Efficacious, Lapatanib-Derived Lead Compound for Trypanosomiasis

  摘要：

  Human African trypanosomiasis (HAT) is a neglected tropical disease caused by the protozoan parasite Trypanosoma brucei. Because drugs in use against HAT are toxic and require intravenous dosing, new drugs are needed. Initiating lead discovery campaigns by using chemical scaffolds from drugs approved for other indications can speed up drug discovery for neglected diseases. We demonstrated recently that the 4-anilinoquinazolines lapatinib (GW572016, 1) and canertinib (CI-1033) kill T. brucei with low micromolar EC50 values. We now report promising activity of analogues of 1, which provided an excellent starting point for optimization of the chemotype. Our compound optimization that has led to synthesis of several potent 4-anilinoquinazolines, including NEU617, 23a, a highly potent, orally bioavailable inhibitor of trypanosome replication. At the cellular level, 23a blocks duplication of the kinetoplast and arrests cytokinesis, making it a new chemical tool for studying regulation of the trypanosome cell cycle.

  DOI：

  10.1021/jm400349k
• 作为产物：
  描述：

  2-氯-4-硝基苯酚 在 potassium carbonate 、 氯化铵 、 锌 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 4-(3-methoxybenzyloxy)-3-chlorobenzenamine
  参考文献：
  名称：

  Kinase Scaffold Repurposing for Neglected Disease Drug Discovery: Discovery of an Efficacious, Lapatanib-Derived Lead Compound for Trypanosomiasis

  摘要：

  Human African trypanosomiasis (HAT) is a neglected tropical disease caused by the protozoan parasite Trypanosoma brucei. Because drugs in use against HAT are toxic and require intravenous dosing, new drugs are needed. Initiating lead discovery campaigns by using chemical scaffolds from drugs approved for other indications can speed up drug discovery for neglected diseases. We demonstrated recently that the 4-anilinoquinazolines lapatinib (GW572016, 1) and canertinib (CI-1033) kill T. brucei with low micromolar EC50 values. We now report promising activity of analogues of 1, which provided an excellent starting point for optimization of the chemotype. Our compound optimization that has led to synthesis of several potent 4-anilinoquinazolines, including NEU617, 23a, a highly potent, orally bioavailable inhibitor of trypanosome replication. At the cellular level, 23a blocks duplication of the kinetoplast and arrests cytokinesis, making it a new chemical tool for studying regulation of the trypanosome cell cycle.

  DOI：

  10.1021/jm400349k

文献信息

• PROTOZOAN PARASITE GROWTH INHIBITORS
  申请人：Northeastern University

  公开号：US20150259331A1

  公开（公告）日：2015-09-17

  Compounds and methods for inhibiting growth of a protozoan parasite. Methods of treating a protozoan parasite infection in a subject by administering a therapeutically effective amount of a compound as disclosed herein. The compounds and methods can be used to inhibit growth of protozoan parasites such as Trypanosoma brucei, Trypanosoma cruzi, Leishmania spp., and Plasmodium spp.

  用于抑制原生动物寄生虫生长的化合物和方法。通过向主体施用如本文所述的治疗有效量的化合物来治疗原生动物寄生虫感染的方法。这些化合物和方法可用于抑制如非洲锥虫、克鲁兹锥虫、利什曼原虫属和疟原虫属等原生动物寄生虫的生长。
• CYANOQUINOLINE DERIVATIVES
  申请人：Zhang Hesheng

  公开号：US20130225579A1

  公开（公告）日：2013-08-29

  Disclosed is a compound of formula I, a stereoisomer thereof, a cis-trans-isomer thereof, a tautomer thereof, or a mixture thereof, or a pharmaceutically acceptable salt thereof, a solvate thereof or a prodrug thereof, wherein R 1 , R 2 , R 3 and R 4 are each as defined in the present application.

  公开了一种公式I的化合物，其立体异构体，其顺反异构体，其互变异构体，或它们的混合物，或其药物可接受的盐，其溶剂化物或其前药，其中R1，R2，R3和R4各自如在本申请中定义。
• Cyanoquinoline derivatives
  申请人：Tianjin Hemay Oncoloy Pharmaceutical Co., Ltd.

  公开号：US10246443B2

  公开（公告）日：2019-04-02

  Disclosed is a compound of formula I, a stereoisomer thereof, a cis-trans-isomer thereof, a tautomer thereof, or a mixture thereof, or a pharmaceutically acceptable salt thereof, a solvate thereof or a prodrug thereof, wherein R1, R2, R3 and R4 are each as defined in the present application.

  公开了一种式 I 的化合物、其立体异构体、顺反异构体、同系物或其混合物，或其药学上可接受的盐、溶液或原药、 其中 R1、R2、R3 和 R4 各如本申请中所定义。
• PHTHALANILATE COMPOUNDS AND METHODS OF USE
  申请人：Mobashery Shahriar

  公开号：US20120232150A1

  公开（公告）日：2012-09-13

  The invention provides antimicrobial compounds and compositions, and methods of using them. The compounds and compositions include, for example, a compound of any one of Formulas I-X. The invention further provides methods of preparing the compounds, and useful intermediates for their preparation. The compounds can possess highly specific and selective activity, such as antibacterial activity and/or enzymatic inhibitory activity. Accordingly, the compounds and compositions can be used to treat bacterial infections, or to inhibit or kill bacteria, either in vitro or in vivo.
• US8859620B2
  申请人：——

  公开号：US8859620B2

  公开（公告）日：2014-10-14