(RS)-2-[2-(3-acetyl-4-chloro-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione | 1356452-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-2-[2-(3-acetyl-4-chloro-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: Acetyl-4-chloro-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione；2-[1-(3-acetyl-4-chloro-2,6-dimethylphenoxy)propan-2-yl]isoindole-1,3-dione
• CAS: 1356452-01-1
• 化学式: C₂₁H₂₀ClNO₄
• 分子量: 385.847
• InChiKey: CKXDDMDNMIGHOK-UHFFFAOYSA-N

物化性质

• 沸点：
  515.8±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-2-[2-(3-acetyl-4-chloro-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 在 sodium formate 、 palladium diacetate 、 间氯过氧苯甲酸 、 2-(二叔丁基膦)联苯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (RS)-3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]-2,4-dimethylphenyl acetate
  参考文献：
  名称：

  Synthesis and Toxicopharmacological Evaluation ofm-Hydroxymexiletine, the First Metabolite of Mexiletine More Potent Than the Parent Compound on Voltage-Gated Sodium Channels

  摘要：

  The first synthesis of m-hydroxymexiletine (MHM) has been accomplished. MHM displayed hNav1.5 sodium channel blocking activity, and tests indicate it to be similar to 2-fold more potent than the parent mexiletine and to have more favorable toxicological properties than mexiletine. Thus, MHM and possible related prodrugs might be studied as agents for the treatment of arrhythmias, neuropathic pain, and myotonias in substitution of mexiletine (metabolite switch), which has turned out to be tainted with common toxicity.

  DOI：

  10.1021/jm201197z
• 作为产物：
  描述：

  2-(2-羟基-1-甲基乙基)-1H-异吲哚-1,3(2H-)-二酮 在 aluminum (III) chloride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (RS)-2-[2-(3-acetyl-4-chloro-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and Toxicopharmacological Evaluation ofm-Hydroxymexiletine, the First Metabolite of Mexiletine More Potent Than the Parent Compound on Voltage-Gated Sodium Channels

  摘要：

  The first synthesis of m-hydroxymexiletine (MHM) has been accomplished. MHM displayed hNav1.5 sodium channel blocking activity, and tests indicate it to be similar to 2-fold more potent than the parent mexiletine and to have more favorable toxicological properties than mexiletine. Thus, MHM and possible related prodrugs might be studied as agents for the treatment of arrhythmias, neuropathic pain, and myotonias in substitution of mexiletine (metabolite switch), which has turned out to be tainted with common toxicity.

  DOI：

  10.1021/jm201197z

文献信息

• Synthesis and Toxicopharmacological Evaluation of<i>m</i>-Hydroxymexiletine, the First Metabolite of Mexiletine More Potent Than the Parent Compound on Voltage-Gated Sodium Channels
  作者：Alessia Catalano、Jean-François Desaphy、Giovanni Lentini、Alessia Carocci、Antonia Di Mola、Claudio Bruno、Roberta Carbonara、Annalisa De Palma、Roberta Budriesi、Carla Ghelardini、Maria Grazia Perrone、Nicola Antonio Colabufo、Diana Conte Camerino、Carlo Franchini

  DOI：10.1021/jm201197z

  日期：2012.2.9

  The first synthesis of m-hydroxymexiletine (MHM) has been accomplished. MHM displayed hNav1.5 sodium channel blocking activity, and tests indicate it to be similar to 2-fold more potent than the parent mexiletine and to have more favorable toxicological properties than mexiletine. Thus, MHM and possible related prodrugs might be studied as agents for the treatment of arrhythmias, neuropathic pain, and myotonias in substitution of mexiletine (metabolite switch), which has turned out to be tainted with common toxicity.