ethyl 3-[(1-methyl-1-silacyclopentan-1-yl)methyl]-2-cyanopropionate | 1403674-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-[(1-methyl-1-silacyclopentan-1-yl)methyl]-2-cyanopropionate
• 英文别名: Ethyl 2-cyano-3-(1-methylsilolan-1-yl)propanoate；ethyl 2-cyano-3-(1-methylsilolan-1-yl)propanoate
• CAS: 1403674-21-4
• 化学式: C₁₁H₁₉NO₂Si
• 分子量: 225.363
• InChiKey: PLLLLYARJNQZKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氰乙酸乙酯 、 1-氯甲基-1-甲基-1-硅杂环戊烷 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 38.0h， 以64%的产率得到ethyl 3-[(1-methyl-1-silacyclopentan-1-yl)methyl]-2-cyanopropionate
  参考文献：
  名称：

  SILICON-CONTAINING CARBOXYLIC ACID DERIVATIVE

  摘要：

  由式(I)表示的化合物[R1至R8表示烷基基团、烯基基团等；n表示0或1；R4表示氨基团或—(CX2)m—COOH（m表示0到3，X表示氢原子）；R5表示—(CY2)p—COOR6（p表示0到3，Y表示氢原子，R6表示氢原子或烷基基团）]，或其盐。

  公开号：

  US20140031575A1

文献信息

• SILICON-CONTAINING CARBOXYLIC ACID DERIVATIVE
  申请人：Muratake Hideaki

  公开号：US20140031575A1

  公开（公告）日：2014-01-30

  A compound represented by the formula (I) [R 1 to R 8 represent an alkyl group, an alkenyl group, and the like; n represents 0 or 1; R 4 represents an amino group or —(CX 2 ) m —COOH (m represents 0 to 3, and X represents hydrogen atom); R 5 represents —(CY 2 ) p —COOR 6 (p represents an 0 to 3, Y represents hydrogen atom, and R 6 represents hydrogen atom or an alkyl group)], or a salt thereof.

  由式(I)表示的化合物[R1至R8表示烷基基团、烯基基团等；n表示0或1；R4表示氨基团或—(CX2)m—COOH（m表示0到3，X表示氢原子）；R5表示—(CY2)p—COOR6（p表示0到3，Y表示氢原子，R6表示氢原子或烷基基团）]，或其盐。
• Silicon-Containing GABA Derivatives, Silagaba Compounds, as Orally Effective Agents for Treating Neuropathic Pain without Central-Nervous-System-Related Side Effects
  作者：Hiroshi Fukasawa、Hideaki Muratake、Ai Ito、Hideyuki Suzuki、Yohei Amano、Marina Nagae、Kiyoshi Sugiyama、Koichi Shudo

  DOI：10.1021/cn500053d

  日期：2014.7.16

  Neuropathic pain is a chronic condition resulting from neuronal damage. Pregabalin, the (S)-isomer of 3-isobutyl-gamma-aminobutyric acid (GABA), is widely used to treat neuropathic pain, despite the occurrence of central nervous system (CNS)-related side effects such as dizziness and somnolence. Here we describe the pharmacology of novel GABA derivatives containing silicon-carbon bonds, silagaba compounds. Silagaba131, 132, and 161 showed pregabalin-like analgesic activities in animal models of neuropathic pain, but in contrast to pregabalin they did not impair neuromuscular coordination in rotarod tests. Pharmacokinetic studies showed that brain exposure to silagaba compounds was lower than that to pregabalin. Surprisingly, despite their potent analgesic action in vivo, silagaba compounds showed only weak binding to alpha 2-delta protein. These compounds may be useful to study mechanisms of neuropathic pain. Our results also indicate that silagaba132 and 161 are candidates for orally effective treatment of neuropathic pain without CNS-related side effects.