5-bromo-3,4-dibromo-6-<(3-pyridinylmethyl)amino>-2-methylpyrimidin-4-one | 105805-96-7

• 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-3,4-dibromo-6-<(3-pyridinylmethyl)amino>-2-methylpyrimidin-4-one
• 英文别名: 5-bromo-2-methyl-6-[(3-pyridinylmethyl)amino]-4-pyrimidinol；5-Bromo-2-methyl-6-{[(pyridin-3-yl)methyl]amino}pyrimidin-4(1H)-one；5-bromo-2-methyl-4-(pyridin-3-ylmethylamino)-1H-pyrimidin-6-one
• CAS: 105805-96-7
• 化学式: C₁₁H₁₁BrN₄O
• 分子量: 295.139
• InChiKey: ALVGVSNLGSNJPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-3,4-dibromo-6-<(3-pyridinylmethyl)amino>-2-methylpyrimidin-4-one 、 盐酸 生成 5-bromo-2-methyl-6-(pyridin-3-ylmethylamino)-1H-pyrimidin-4-one;hydrochloride
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯-4-羟基-2-甲基嘧啶 在 溴 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 氯仿 为溶剂， 反应 21.0h， 生成 5-bromo-3,4-dibromo-6-<(3-pyridinylmethyl)amino>-2-methylpyrimidin-4-one
  参考文献：
  名称：

  Chemistry and positive inotropic effect of pelrinone and related derivatives. A novel class of 2-methylpyrimidones as inotropic agents

  摘要：

  A novel series of pyrimidine derivatives was synthesized and evaluated for positive inotropic activity. Inotropic and chronotropic effects were determined in vitro in cat papillary muscle and right atrium, respectively. Selected compounds were then evaluated in vivo in a dog heart failure model. Changes in ventricular dP/dt, heart rate, and blood pressure were monitored. Several of these agents produced relatively minor changes in heart rate. This class of agents demonstrated a varying degree of vasodilator effects concomitant with increases in ventricular contractility. The most potent analogues, 9, 48, and 49, were evaluated orally in conscious dogs with implanted Konisberg pressure transducers, and their effect on left ventricular dP/dt was compared with that of milrinone. Mechanistically, the agents of this novel class appear not to mediate their effect via beta-receptors or inhibition of Na+/K+-ATPase. A major component of their inotropic effect is mediated by the inhibition of cardiac phosphodiesterase (PDE)-Fr. III. This was clearly demonstrated by 9, 48, and 49. Compound 48 was found to be the most potent inhibitor of PDE-Fr. III from among the compounds tested in this assay.

  DOI：

  10.1021/jm00399a023

文献信息

• 5-Substituted-6-aminopyrimidine derivatives, composition and uses
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0210025A2

  公开（公告）日：1987-01-28

  Herein disclosed are aminopyrimidine derivatives having the formula or tautomeric form thereof, wherein R is halogen or lower alkyl containing 1 to 3 carbon atoms; R' is hydrogen, hydroxy, cyclopropyl, pyridinyl, 1-methyl-1H-pyrrol-2-yl, 2-furanyl, phenyl: and n is an integer from 1 to 3, providing that when R' is hydroxy n is 2 or 3, and the pharmaceutically acceptable addition salts thereof. Also disclosed are processes for their preparation and methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for increasIng cardiac contractility in a mammal.

  这里公开了具有式或其同分异构体形式的氨基嘧啶衍生物，其中R是卤素或含有1至3个碳原子的低级烷基；R'是氢、羟基、环丙基、吡啶基、1-甲基-1H-吡咯-2-基、2-呋喃基、苯基；n是1至3的整数，但当R'是羟基时，n是2或3，以及其药学上可接受的加成盐。 还公开了其制备工艺和使用这些衍生物和药物组合物的方法。 这些衍生物可用于增加哺乳动物的心脏收缩力。
• BAGLI, JEHAN;BOGRI, T.;PALAMETA, B.;RAKHIT, S.;PESECKIS, S.;MCQUILLAN, J.+, J. MED. CHEM., 31,(1988) N 4, 814-823
  作者：BAGLI, JEHAN、BOGRI, T.、PALAMETA, B.、RAKHIT, S.、PESECKIS, S.、MCQUILLAN, J.+

  DOI：——

  日期：——
• ——
  作者：BAGLI J. F.、 PESECKIS S. M.

  DOI：——

  日期：——
• US4617393A
  申请人：——

  公开号：US4617393A

  公开（公告）日：1986-10-14
• Chemistry and positive inotropic effect of pelrinone and related derivatives. A novel class of 2-methylpyrimidones as inotropic agents
  作者：Jehan Bagli、T. Bogri、B. Palameta、S. Rakhit、S. Peseckis、J. McQuillan、D. K. H. Lee

  DOI：10.1021/jm00399a023

  日期：1988.4

  A novel series of pyrimidine derivatives was synthesized and evaluated for positive inotropic activity. Inotropic and chronotropic effects were determined in vitro in cat papillary muscle and right atrium, respectively. Selected compounds were then evaluated in vivo in a dog heart failure model. Changes in ventricular dP/dt, heart rate, and blood pressure were monitored. Several of these agents produced relatively minor changes in heart rate. This class of agents demonstrated a varying degree of vasodilator effects concomitant with increases in ventricular contractility. The most potent analogues, 9, 48, and 49, were evaluated orally in conscious dogs with implanted Konisberg pressure transducers, and their effect on left ventricular dP/dt was compared with that of milrinone. Mechanistically, the agents of this novel class appear not to mediate their effect via beta-receptors or inhibition of Na+/K+-ATPase. A major component of their inotropic effect is mediated by the inhibition of cardiac phosphodiesterase (PDE)-Fr. III. This was clearly demonstrated by 9, 48, and 49. Compound 48 was found to be the most potent inhibitor of PDE-Fr. III from among the compounds tested in this assay.