(R)-7-chloro-2-(phthalimidomethyl)-1,4-benzodioxane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (R)-7-chloro-2-(phthalimidomethyl)-1,4-benzodioxane
• 英文别名: 2-[[(3R)-6-chloro-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]isoindole-1,3-dione
• 化学式: C₁₇H₁₂ClNO₄
• 分子量: 329.74
• InChiKey: PBRQGGFLYFWNMK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯邻苯二酚 、 (S)-(+)-对甲苯磺酸缩水甘油酯 、 potassium phtalimide 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 (R)-7-chloro-2-(phthalimidomethyl)-1,4-benzodioxane 、
  参考文献：
  名称：

  Novel, Broad-Spectrum Anticonvulsants Containing a Sulfamide Group: Pharmacological Properties of (S)-N-[(6-Chloro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]sulfamide (JNJ-26489112)

  摘要：

  Broad-spectrum anticonvulsants are of considerable interest as antiepileptic drugs, especially because of their potential for treating refractory patients. Such "neurostabilizers" have also been used to treat other neurological disorders, including migraine, bipolar disorder, and neuropathic pain. We synthesized a series of sulfamide derivatives (4-9, 10a-i, 11a, 11b, 12) and evaluated their anticonvulsant activity. Thus, we identified promising sulfamide 4 (JNJ-26489112) and explored its pharmacological properties. Compound 4 exhibited excellent anticonvulsant activity in rodents against audiogenic, electrically induced, and chemically induced seizures. Mechanistically, 4 inhibited voltage-gated Na+ channels and N-type Ca2+ channels and was effective as a K+ channel opener. The anticonvulsant profile of 4 suggests that it may be useful for treating multiple forms of epilepsy (generalized tonic-clonic, complex partial, absence seizures), including refractory (or pharmacoresistant) epilepsy, at dose levels that confer a good safety margin. On the basis of its pharmacology and other favorable characteristics, 4 was advanced into human clinical studies.

  DOI：

  10.1021/jm400894u

文献信息

• 1-Amido-3-(2-hydroxyphenoxy)-2-propanol derivatives and a process for preparing 2-amidomethyl-1,4-benzodioxane derivatives
  申请人：Miki Yasushi

  公开号：US20060019993A1

  公开（公告）日：2006-01-26

  An 1-amido-3-(2-hydroxyphenoxy)-2-propanol derivative represented by the following formula (1), wherein cycle A may have further 1 to 4 substituents, and said substituent means a substituent selected from the group consisting of saturated or unsaturated C1-4 alkyl group, aralkyl group in which alkyl moiety has 1 to 4 carbon atoms, aryl group, halogen atom, halogenated C1-4 alkyl group, C2-5 alkanoyl group, mono or dialkylcarbamoyl group in which alkyl moiety has 1 to 4 carbon atoms, cyano group and nitro group, and the substituents at positions 3 and 6, or at positions 4 and 5 on the cycle A are different each other. Other ring may be fused at positions 3 and 4, or at positions 5 and 6 on the cycle A to form a condensed polycyclic hydrocarbon with the cycle A. R 1 is alkanoyl group or aroyl group, and R 2 is hydrogen atom, alkanoyl group or aroyl group, or R 1 and R 2 may be combined together with the N atom to form a cyclic imido group, which is useful as an intermediate of medicines, etc.

  由以下公式（1）表示的1-酰胺-3-(2-羟基苯氧基)-2-丙醇衍生物，其中环A可能有进一步的1到4个取代基，所述取代基是从饱和或不饱和的C1-4烷基，含有1到4个碳原子的芳基烷基，芳基，卤素原子，卤代C1-4烷基，C2-5烷酰基，单或二烷基氨基基，其中烷基部分含有1到4个碳原子，氰基和硝基中选择的取代基，并且在环A上的位置3和6，或在位置4和5上的取代基彼此不同。其他环可能在环A上的位置3和4，或在位置5和6上与环A融合，形成与环A的紧缩多环碳氢化合物。R1是烷酰基或芳酰基，R2是氢原子，烷酰基或芳酰基，或R1和R2可以与N原子结合在一起形成环亚胺基团，可用作药物等的中间体。
• 1-amido-3-(2-hydroxyphenoxy)-2-propanol derivatives and a process for preparing 2-amidomethyl-1, 4-benzodioxane derivatives
  申请人：DAISO CO., LTD.

  公开号：EP1619183B1

  公开（公告）日：2008-10-01
• US7368608B2
  申请人：——

  公开号：US7368608B2

  公开（公告）日：2008-05-06