3-(4-bromobenzyl)-3H-pyrimidin-4-one | 1236363-54-4

• 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: 3-(4-bromobenzyl)-3H-pyrimidin-4-one
• 英文别名: 3-[(4-Bromophenyl)methyl]-3,4-dihydropyrimidin-4-one；3-[(4-bromophenyl)methyl]pyrimidin-4-one
• CAS: 1236363-54-4
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: FGUJNLWQTGGBIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzyl)-3H-pyrimidin-4-one 、 C₁₈H₂₆BNO₄S₂ 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 以31%的产率得到3-[4-(6-oxo-6H-pyrimidin-1-yl-methyl)-phenyl]-5-isobutyl-N-tert-butylthiophene-2-sulfonamide
  参考文献：
  名称：

  Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition

  摘要：

  Structural alterations to the benzylic position of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed, with the emphasis to reduce the CYP 450 inhibitory property of the initial structure. The imidazole moiety, responsible for the CYP 450 inhibitory effect in 1, was replaced with various heterocycles. In addition, the modes of attachment of the heterocycles, that is, carbon versus nitrogen attachment, and introduction of carbonyl functionalities to the benzylic position have been evaluated. In all the three series, AT(2) receptor ligands with affinity in the lower nanomolar range were identified. None of the analogues, regardless of the substituents, exhibited any affinity for the AT(1) receptor. Compounds with substantially reduced inhibition of the CYP 450 enzymes were obtained. Among them the compound 60 was found to induce neurite elongation in NG 108-15 cells and served as potent AT(2) selective agonist. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.064
• 作为产物：
  描述：

  4(3H)-嘧啶酮 、 对溴溴苄 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以78%的产率得到3-(4-bromobenzyl)-3H-pyrimidin-4-one
  参考文献：
  名称：

  Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition

  摘要：

  Structural alterations to the benzylic position of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed, with the emphasis to reduce the CYP 450 inhibitory property of the initial structure. The imidazole moiety, responsible for the CYP 450 inhibitory effect in 1, was replaced with various heterocycles. In addition, the modes of attachment of the heterocycles, that is, carbon versus nitrogen attachment, and introduction of carbonyl functionalities to the benzylic position have been evaluated. In all the three series, AT(2) receptor ligands with affinity in the lower nanomolar range were identified. None of the analogues, regardless of the substituents, exhibited any affinity for the AT(1) receptor. Compounds with substantially reduced inhibition of the CYP 450 enzymes were obtained. Among them the compound 60 was found to induce neurite elongation in NG 108-15 cells and served as potent AT(2) selective agonist. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.064

文献信息

• Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition
  作者：A.K. Mahalingam、Yiqian Wan、A.M.S. Murugaiah、Charlotta Wallinder、Xiongyu Wu、Bianca Plouffe、Milad Botros、Fred Nyberg、Anders Hallberg、Nicole Gallo-Payet

  DOI：10.1016/j.bmc.2010.03.064

  日期：2010.6.15

  Structural alterations to the benzylic position of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed, with the emphasis to reduce the CYP 450 inhibitory property of the initial structure. The imidazole moiety, responsible for the CYP 450 inhibitory effect in 1, was replaced with various heterocycles. In addition, the modes of attachment of the heterocycles, that is, carbon versus nitrogen attachment, and introduction of carbonyl functionalities to the benzylic position have been evaluated. In all the three series, AT(2) receptor ligands with affinity in the lower nanomolar range were identified. None of the analogues, regardless of the substituents, exhibited any affinity for the AT(1) receptor. Compounds with substantially reduced inhibition of the CYP 450 enzymes were obtained. Among them the compound 60 was found to induce neurite elongation in NG 108-15 cells and served as potent AT(2) selective agonist. (C) 2010 Elsevier Ltd. All rights reserved.