5-(Bromoethynyl)-4-iodo-6-methoxypyrimidine | 86854-60-6

• 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-(Bromoethynyl)-4-iodo-6-methoxypyrimidine
• 英文别名: 5-(2-bromoethynyl)-4-iodo-6-methoxypyrimidine
• CAS: 86854-60-6
• 化学式: C₇H₄BrIN₂O
• 分子量: 338.93
• InChiKey: OYKAQEHFYUSMPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(Bromoethynyl)-4-iodo-6-methoxypyrimidine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 4,5-二乙炔基-6-甲氧基嘧啶
  参考文献：
  名称：

  Synthesis and chemistry of 1,3-diazabiphenylenes

  摘要：

  DOI：

  10.1021/jo00176a014
• 作为产物：
  描述：

  4,6-二氯-5-嘧啶甲醛 在 氢碘酸 、 三苯基膦 、 锌 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成 5-(Bromoethynyl)-4-iodo-6-methoxypyrimidine
  参考文献：
  名称：

  Synthesis and chemistry of 1,3-diazabiphenylenes

  摘要：

  DOI：

  10.1021/jo00176a014

文献信息

• 4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors
  作者：Mark A. Matulenko、Ernest S. Paight、Robin R. Frey、Arthur Gomtsyan、Stanley DiDomenico、Meiqun Jiang、Chih-Hung Lee、Andrew O. Stewart、Haixia Yu、Kathy L. Kohlhaas、Karen M. Alexander、Steve McGaraughty、Joseph Mikusa、Kennan C. Marsh、Steven W. Muchmore、Clarissa L. Jakob、Elizabeth A. Kowaluk、Michael F. Jarvis、Shripad S. Bhagwat

  DOI：10.1016/j.bmc.2006.12.029

  日期：2007.2

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and transilience of a 1,3-diazabiphenylene
  作者：Marc d'Alarcao、Nelson J. Leonard

  DOI：10.1021/ja00356a063

  日期：1983.9
• DALARCAO, M.;LEONARD, N. J., J. AMER. CHEM. SOC., 1983, 105, N 18, 5958-5960
  作者：DALARCAO, M.、LEONARD, N. J.

  DOI：——

  日期：——
• BAKTHAVACHALAM, VENKATESALU;DALARCAO, M.;LEONARD, N. J., J. ORG. CHEM., 1984, 49, N 2, 289-295
  作者：BAKTHAVACHALAM, VENKATESALU、DALARCAO, M.、LEONARD, N. J.

  DOI：——

  日期：——
• Synthesis and chemistry of 1,3-diazabiphenylenes
  作者：Venkatesalu Bakthavachalam、Marc D'Alarcao、Nelson J. Leonard

  DOI：10.1021/jo00176a014

  日期：1984.1