methyl 5-(2-bromoacetyl)-2-ethoxybenzoate | 76310-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-(2-bromoacetyl)-2-ethoxybenzoate
• CAS: 76310-73-1
• 化学式: C₁₂H₁₃BrO₄
• 分子量: 301.137
• InChiKey: GWINPALDLMMDOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-bromoacetyl)-2-ethoxybenzoate 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 5-(2-(4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)acetyl)-2-(ethoxy)benzoic acid
  参考文献：
  名称：

  取代的苯甲酰胍衍生物作为强Na + / H +交换抑制剂的合成和生物活性

  摘要：

  设计并合成了一系列新的取代的苯甲酰基胍衍生物，以评估其对NHE1的抑制活性。发现其中大多数以浓度依赖的方式抑制NHE1介导的血小板肿胀，并且有8种化合物显示出比Cariporide更有效的NHE1抑制活性。化合物6F与IC 50 1.08×10的值-10莫尔-1，为39倍以上的铅化合物的CPU-X-050420更有效的体外试验。

  DOI：

  10.1002/cjoc.201180470
• 作为产物：
  描述：

  5-乙酰水杨酸甲酯 在 溴 、 potassium carbonate 、 potassium iodide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 methyl 5-(2-bromoacetyl)-2-ethoxybenzoate
  参考文献：
  名称：

  取代的苯甲酰胍衍生物作为强Na + / H +交换抑制剂的合成和生物活性

  摘要：

  设计并合成了一系列新的取代的苯甲酰基胍衍生物，以评估其对NHE1的抑制活性。发现其中大多数以浓度依赖的方式抑制NHE1介导的血小板肿胀，并且有8种化合物显示出比Cariporide更有效的NHE1抑制活性。化合物6F与IC 50 1.08×10的值-10莫尔-1，为39倍以上的铅化合物的CPU-X-050420更有效的体外试验。

  DOI：

  10.1002/cjoc.201180470

文献信息

• 2-Hydroxy-5-(1-hydroxy-2-piperazinylethyl)-benzoic acid derivatives
  申请人：Richardson-Merrell Inc.

  公开号：US04255575A1

  公开（公告）日：1981-03-10

  Derivatives of 2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoic acid are prepared which are useful for their blocking action on .alpha. and .beta.-adrenergic receptors. In addition, these compounds are useful as spasmolytic and antihypertensive agents.

  制备了2-羟基-5-(1-羟基-2-哌嗪基乙基)苯甲酸的衍生物，这些衍生物对α和β肾上腺素受体的阻滞作用很有用。此外，这些化合物还可用作解痉和降压药物。
• Salicylamide derivatives related to medroxalol with .alpha.- and .beta.-adrenergic antagonist and antihypertensive activity
  作者：J. Martin Grisar、George P. Claxton、Thomas M. Bare、Richard C. Dage、Hsien C. Cheng、James K. Woodward

  DOI：10.1021/jm00135a017

  日期：1981.3

  Analogues of medroxalol (1) were prepared in which the carboxamide function, the phenolic hydroxy group, and the aralkylamine side chain were modified. N-alkyl-substituted amide analogues of 1 showed diminishing beta-blocking activity with increasing steric bulk of the alkyl group. This allowed the conclusion that deactivation of the phenolic hydroxy group of 1 by the carbonyl group of the amide function is responsible for the beta-adrenergic antagonistic properties of 1. This conclusion was strengthened by the finding that the phenolic O-methyl analogue 5-[2-[[3-(1,3-benzodioxol-5-yl)-1-methylpropyl]amino]-1hydroxyethyl]-2-methoxybenzamide (13) was found to have enhanced beta-adrenergic blocking activity. The finding that 13 also had decreased alpha-blocking activity compared to 1 indicated that the phenolic hydroxy group of 1 enhances alpha-adrenergic antagonism. The finding that 1 and 13 showed such a large difference in relative alpha- to beta-blocking potency while exhibiting approximately equal antihypertensive activity in spontaneously hypertensive rats was surprising. In indicated that pharmacologic properties other than alpha- and beta-adrenergic blockade may contribute to the antihypertensive activity of medroxalol. One of the analogues in which the aralkylamine side chain of 1 was replaced by a fragment of a known alpha-adrenergic receptor blocker, 2-hydroxy-5-[1-hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]benzamide (22), showed an interesting pharmacologic profile of potential therapeutic usefulness.
• US4255575A
  申请人：——

  公开号：US4255575A

  公开（公告）日：1981-03-10
• Synthesis and Bioactivity of Substituted Benzoylguanidine Derivatives as Potent Na+/H+ Exchanger Inhibitors
  作者：Ning Jin、Yun Yang、Wenting Xu、Xiaozhi Yang、Guoqing Gong、Yungen Xu

  DOI：10.1002/cjoc.201180470

  日期：2012.2

  A novel series of substituted benzoylguanidine derivatives were designed and synthesized in order to evaluate their NHE1 inhibitory activity. Most of them were found to inhibit NHE1‐mediated platelet swelling in a concentration‐dependent manner, and eight compounds showed more potent NHE1 inhibitory activity than Cariporide. Compound 6f with an IC50 value of 1.08×10−10 mol·L−1, was 39 times more potent

  设计并合成了一系列新的取代的苯甲酰基胍衍生物，以评估其对NHE1的抑制活性。发现其中大多数以浓度依赖的方式抑制NHE1介导的血小板肿胀，并且有8种化合物显示出比Cariporide更有效的NHE1抑制活性。化合物6F与IC 50 1.08×10的值-10莫尔-1，为39倍以上的铅化合物的CPU-X-050420更有效的体外试验。