2-(benzyloxy)-6-bromoquinoline | 300811-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(benzyloxy)-6-bromoquinoline
• 英文别名: 6-Bromo-2-phenylmethoxyquinoline；6-bromo-2-phenylmethoxyquinoline
• CAS: 300811-62-5
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: MFAWGDJUSWPYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-6-bromoquinoline 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Chiral Discrimination in Hydrogen-Bonded [7]Helicenes

  摘要：

  [GRAPHICS]A series of racemic [7]helicenes have been prepared and characterized both in solution and in the solid state. Despite the helicenes having the ability to self-assemble in a variety of stereochemical and topological relationships, they formed only enantiomerically pure dimers held together by two pairs of cooperative hydrogen bonds. The self-assembly process was enantiospecific in solution and diastereoselective in the crystal.

  DOI：

  10.1021/ol006366y
• 作为产物：
  描述：

  6-溴喹啉-2-酮 、 溴甲苯 在 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-(benzyloxy)-6-bromoquinoline
  参考文献：
  名称：

  Development of potent and selective Plasmodium falciparum calcium-dependent protein kinase 4 (PfCDPK4) inhibitors that block the transmission of malaria to mosquitoes

  摘要：

  Malaria remains a major health concern for a large percentage of the world's population. While great strides have been made in reducing mortality due to malaria, new strategies and therapies are still needed. Therapies that are capable of blocking the transmission of Plasmodium parasites are particularly attractive, but only primaquine accomplishes this, and toxicity issues hamper its widespread use. In this study, we describe a series of pyrazolopyrimidine- and imidazopyrazine-based compounds that are potent inhibitors of PfCDPK4, which is a calcium-activated Plasmodium protein lcinase that is essential for exflagellation of male gametocytes. Thus, PfCDPK4 is essential for the sexual development of Plasmodium parasites and their ability to infect mosquitoes. We demonstrate that two structural features in the ATPbinding site of PfCDPK4 can be exploited in order to obtain potent and selective inhibitors of this enzyme. Furthermore, we demonstrate that pyrazolopyrimidine-based inhibitors that are potent inhibitors of the in vitro activity of PfCDPK4 are also able to block Plasmodium falciparum exflagellation with no observable toxicity to human cells. This medicinal chemistry effort serves as a valuable starting point in the development of safe, transmission-blocking agents for the control of malaria. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.048

文献信息

• INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：INFINITY PHARMACEUTICALS, INC.

  公开号：US20150368278A1

  公开（公告）日：2015-12-24

  The present invention provides compounds, and pharmaceutically acceptable compositions thereof, encompassed by any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof. The present invention also provides methods for treating an FAAH mediated disease, disorder or condition by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof. Additionally, the present invention provides methods for inhibiting FAAH by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof.

  本发明提供了由任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物及其药学上可接受的组合物所包含的范围，或其亚属所包含的范围。本发明还提供了通过向需要的患者投与任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物或其组合物的治疗有效量来治疗FAAH介导的疾病、紊乱或症状的方法。此外，本发明提供了通过向需要的患者投与任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物或其组合物的治疗有效量来抑制FAAH的方法。
• Pd-Catalyzed Chemoselective O-Benzylation of Ambident 2-Quinolinone Nucleophiles
  作者：Melissa Cadena、Roberto Silva Villatoro、Jyoti Shah Gupta、Cody Phillips、Jonathan B. Allen、Hadi D. Arman、Daniel J. Wherritt、Nicholas A. Clanton、Alexander L. Ruchelman、Eric M. Simmons、Albert J. DelMonte、John R. Coombs、Doug E. Frantz

  DOI：10.1021/acscatal.2c02783

  日期：2022.8.19
• Development of potent and selective Plasmodium falciparum calcium-dependent protein kinase 4 (PfCDPK4) inhibitors that block the transmission of malaria to mosquitoes
  作者：Rama Subba Rao Vidadala、Kayode K. Ojo、Steven M. Johnson、Zhongsheng Zhang、Stephen E. Leonard、Arinjay Mitra、Ryan Choi、Molly C. Reid、Katelyn R. Keyloun、Anna M.W. Fox、Mark Kennedy、Tiffany Silver-Brace、Jen C.C. Hume、Stefan Kappe、Christophe L.M.J. Verlinde、Erkang Fan、Ethan A. Merritt、Wesley C. Van Voorhis、Dustin J. Maly

  DOI：10.1016/j.ejmech.2013.12.048

  日期：2014.3

  Malaria remains a major health concern for a large percentage of the world's population. While great strides have been made in reducing mortality due to malaria, new strategies and therapies are still needed. Therapies that are capable of blocking the transmission of Plasmodium parasites are particularly attractive, but only primaquine accomplishes this, and toxicity issues hamper its widespread use. In this study, we describe a series of pyrazolopyrimidine- and imidazopyrazine-based compounds that are potent inhibitors of PfCDPK4, which is a calcium-activated Plasmodium protein lcinase that is essential for exflagellation of male gametocytes. Thus, PfCDPK4 is essential for the sexual development of Plasmodium parasites and their ability to infect mosquitoes. We demonstrate that two structural features in the ATPbinding site of PfCDPK4 can be exploited in order to obtain potent and selective inhibitors of this enzyme. Furthermore, we demonstrate that pyrazolopyrimidine-based inhibitors that are potent inhibitors of the in vitro activity of PfCDPK4 are also able to block Plasmodium falciparum exflagellation with no observable toxicity to human cells. This medicinal chemistry effort serves as a valuable starting point in the development of safe, transmission-blocking agents for the control of malaria. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Chiral Discrimination in Hydrogen-Bonded [7]Helicenes
  作者：Elisa Murguly、Robert McDonald、Neil R. Branda

  DOI：10.1021/ol006366y

  日期：2000.10.1

  [GRAPHICS]A series of racemic [7]helicenes have been prepared and characterized both in solution and in the solid state. Despite the helicenes having the ability to self-assemble in a variety of stereochemical and topological relationships, they formed only enantiomerically pure dimers held together by two pairs of cooperative hydrogen bonds. The self-assembly process was enantiospecific in solution and diastereoselective in the crystal.