5-bromo-2-(prop-1-en-2-yl)pyrimidine | 1314354-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-bromo-2-(prop-1-en-2-yl)pyrimidine
• 英文别名: 5-bromo-2-prop-1-en-2-ylpyrimidine
• CAS: 1314354-16-9
• 化学式: C₇H₇BrN₂
• 分子量: 199.05
• InChiKey: NFYTXBRLWHNGBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(prop-1-en-2-yl)pyrimidine 在 吡啶 、 四氧化锇 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 生成 1-[5-[2-[1,2-dihydroxy-1-methyl-ethyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea
  参考文献：
  名称：

  Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors

  摘要：

  A series of dual-targeting, alcohol-containing benzothiazoles has been identified with superior antibacterial activity and drug-like properties. Early lead benzothiazoles containing carboxylic acid moieties showed efficacy in a well-established in vivo model, but inferior drug-like properties demanded modifications of functionality capable of demonstrating superior efficacy. Eliminating the acid group in favor of hydrophilic alcohol moieties at C(5), as well as incorporating solubilizing groups at the C(7) position of the core ring provided potent, broad-spectrum Gram-positive antibacterial activity, lower protein binding, and markedly improved efficacy in vivo.

  DOI：

  10.1016/j.bmcl.2014.07.037
• 作为产物：
  描述：

  2-(5-bromopyrimidin-2-yl)propan-2-ol 在 氯化亚砜 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 以54%的产率得到5-bromo-2-(prop-1-en-2-yl)pyrimidine
  参考文献：
  名称：

  [EN] INDAZOLONES AS MODULATORS OF TNF SIGNALING
  [FR] INDAZOLONES UTILISÉES EN TANT QUE MODULATEURS DE LA SIGNALISATION DU TNF

  摘要：

  该披露提供了吲唑酮化合物、药用可接受的盐、前药、生物活性代谢物、立体异构体和同分异构体，其中变量在此处定义。该披露的化合物可能对治疗免疫和肿瘤疾病有用。

  公开号：

  WO2016168633A1

文献信息

• [EN] INDAZOLONES AS MODULATORS OF TNF SIGNALING<br/>[FR] INDAZOLONES UTILISÉES EN TANT QUE MODULATEURS DE LA SIGNALISATION DU TNF
  申请人：ABBVIE INC

  公开号：WO2016168633A1

  公开（公告）日：2016-10-20

  The disclosure provides indazolone compounds, pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the disclosure may be useful for treating immunological and oncological conditions.

  该披露提供了吲唑酮化合物、药用可接受的盐、前药、生物活性代谢物、立体异构体和同分异构体，其中变量在此处定义。该披露的化合物可能对治疗免疫和肿瘤疾病有用。
• Indazolones as modulators of tnf signaling
  申请人：AbbVie Inc.

  公开号：US10160748B2

  公开（公告）日：2018-12-25

  The disclosure provides indazolone compounds, pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the disclosure may be useful for treating immunological and oncological conditions.

  本公开提供了吲唑酮化合物、药学上可接受的盐、原药、生物活性代谢物、立体异构体和异构体，其中变量在本文中定义。本公开的化合物可用于治疗免疫学和肿瘤学疾病。
• INDAZOLONES AS MODULATORS OF TNF SIGNALING
  申请人：AbbVie Inc.

  公开号：EP3294726A1

  公开（公告）日：2018-03-21
• Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors
  作者：James T. Palmer、Lorraine C. Axford、Stephanie Barker、James M. Bennett、Michael Blair、Ian Collins、David T. Davies、Leigh Ford、Carlie T. Gannon、Paul Lancett、Alastair Logan、Christopher J. Lunniss、Craig J. Morton、Daniel A. Offermann、Gary R.W. Pitt、B. Narasinga Rao、Amit K. Singh、Tarun Shukla、Anil Srivastava、Neil R. Stokes、Helena B. Thomaides-Brears、Anju Yadav、David J. Haydon

  DOI：10.1016/j.bmcl.2014.07.037

  日期：2014.9

  A series of dual-targeting, alcohol-containing benzothiazoles has been identified with superior antibacterial activity and drug-like properties. Early lead benzothiazoles containing carboxylic acid moieties showed efficacy in a well-established in vivo model, but inferior drug-like properties demanded modifications of functionality capable of demonstrating superior efficacy. Eliminating the acid group in favor of hydrophilic alcohol moieties at C(5), as well as incorporating solubilizing groups at the C(7) position of the core ring provided potent, broad-spectrum Gram-positive antibacterial activity, lower protein binding, and markedly improved efficacy in vivo.