4'-((2-methyl-4-pyridyl)thio)-2-biphenylcarbonitrile | 171879-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-((2-methyl-4-pyridyl)thio)-2-biphenylcarbonitrile
• 英文别名: 2-[4-(2-Methylpyridin-4-yl)sulfanylphenyl]benzonitrile
• CAS: 171879-81-5
• 化学式: C₁₉H₁₄N₂S
• 分子量: 302.4
• InChiKey: CBVMUNIBBVOBPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-((2-methyl-4-pyridyl)thio)-2-biphenylcarbonitrile 在 trimethyltin azide 、 silica gel 作用下， 生成 2-methyl-4-[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]sulfanylpyridine
  参考文献：
  名称：

  4-(Heteroarylthio)-2-biphenylyltetrazoles as Nonpeptide Angiotensin II Antagonists

  摘要：

  A series of 4-(heteroarylthio)-2-biphenylyltetrazoles was prep are d, and the compounds were examined for their ability to displace [H-3]AII from angiotensin II receptors. Analogues that exhibited significant receptor binding affinities at less than 10 mu M were investigated further for potential antagonism of angiotensin II-mediated contraction of rabbit isolated aortic rings. Three 4-(heteroarylthio)-2-biphenylyltetrazole were identified that exhibited sub-micromolar angiotensin II receptor binding affinities. These compounds and two reference agents, saralasin and losartan (DUP-753), exhibited concentration-dependent reversal of angiotensin II contraction in isolated aortic rings parallel to their receptor binding affinities. Molecular modeling studies were conducted to examine the conformational effects of the novel sulfide bridging unit contained in these 4-(heteroarylthio)-2-biphenylyltetrazoles. The biological effects of the sulfide bridge as well as alterations in the heteroaromatic moiety were investigated, and the resulting structure-activity relationships are discussed.

  DOI：

  10.1021/jm00023a006
• 作为产物：
  描述：

  4-溴茴香硫醚 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 硼酸三异丙酯 、 sodium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.92h， 生成 4'-((2-methyl-4-pyridyl)thio)-2-biphenylcarbonitrile
  参考文献：
  名称：

  4-(Heteroarylthio)-2-biphenylyltetrazoles as Nonpeptide Angiotensin II Antagonists

  摘要：

  A series of 4-(heteroarylthio)-2-biphenylyltetrazoles was prep are d, and the compounds were examined for their ability to displace [H-3]AII from angiotensin II receptors. Analogues that exhibited significant receptor binding affinities at less than 10 mu M were investigated further for potential antagonism of angiotensin II-mediated contraction of rabbit isolated aortic rings. Three 4-(heteroarylthio)-2-biphenylyltetrazole were identified that exhibited sub-micromolar angiotensin II receptor binding affinities. These compounds and two reference agents, saralasin and losartan (DUP-753), exhibited concentration-dependent reversal of angiotensin II contraction in isolated aortic rings parallel to their receptor binding affinities. Molecular modeling studies were conducted to examine the conformational effects of the novel sulfide bridging unit contained in these 4-(heteroarylthio)-2-biphenylyltetrazoles. The biological effects of the sulfide bridge as well as alterations in the heteroaromatic moiety were investigated, and the resulting structure-activity relationships are discussed.

  DOI：

  10.1021/jm00023a006

文献信息

• 4-(Heteroarylthio)-2-biphenylyltetrazoles as Nonpeptide Angiotensin II Antagonists
  作者：Mark H. Norman、H. David Smith、C. Webster Andrews、Flora L. M. Tang、Conrad L. Cowan、Robert P. Steffen

  DOI：10.1021/jm00023a006

  日期：1995.11

  A series of 4-(heteroarylthio)-2-biphenylyltetrazoles was prep are d, and the compounds were examined for their ability to displace [H-3]AII from angiotensin II receptors. Analogues that exhibited significant receptor binding affinities at less than 10 mu M were investigated further for potential antagonism of angiotensin II-mediated contraction of rabbit isolated aortic rings. Three 4-(heteroarylthio)-2-biphenylyltetrazole were identified that exhibited sub-micromolar angiotensin II receptor binding affinities. These compounds and two reference agents, saralasin and losartan (DUP-753), exhibited concentration-dependent reversal of angiotensin II contraction in isolated aortic rings parallel to their receptor binding affinities. Molecular modeling studies were conducted to examine the conformational effects of the novel sulfide bridging unit contained in these 4-(heteroarylthio)-2-biphenylyltetrazoles. The biological effects of the sulfide bridge as well as alterations in the heteroaromatic moiety were investigated, and the resulting structure-activity relationships are discussed.