3-(hydroxymethyl)-1-oxo-1-hydroxyphospholane | 1255533-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 3-(hydroxymethyl)-1-oxo-1-hydroxyphospholane
• 英文别名: (1-Hydroxy-1-oxo-1lambda5-phospholan-3-yl)methanol；(1-hydroxy-1-oxo-1λ5-phospholan-3-yl)methanol
• CAS: 1255533-76-6
• 化学式: C₅H₁₁O₃P
• 分子量: 150.114
• InChiKey: FQNIIZHISNZLER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  isopropoxy-1-oxophosphorinan-4-one 在 盐酸 、 thallium(III) nitrate trihydrate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 3-(hydroxymethyl)-1-oxo-1-hydroxyphospholane
  参考文献：
  名称：

  Novel Cyclic Phosphinic Acids as GABA_C ρ Receptor Antagonists: Design, Synthesis, and Pharmacology

  摘要：

  Understanding the role of GABA(C) receptors in the central nervous system is limited due to a lack of specific ligands. Novel gamma-aminobutyric acid (GABA) analogues based on 3-(aminomethyl)-1-oxo-1-hydroxy-phospholane 17 and 3-(guanido)-1-oxo-1-hydroxy-phospholane 19 were investigated to obtain selective GABA(C) receptor antagonists. A compound of high potency (19, K-B = 10 mu M) and selectivity (greater than 100 times at rho(1) GABA(C) receptors as compared to alpha(1)beta(2)gamma(2L) GABA(A) and GABA(B(1b,2)) receptors) was obtained. The cyclic phosphinic acids (17 and 19) are novel lead agents for developing into more potent and selective GABA(C) receptor antagonists with increased lipophilicity for future in vivo studies.

  DOI：

  10.1021/ml1001344

文献信息

• Novel Cyclic Phosphinic Acids as GABA_C ρ Receptor Antagonists: Design, Synthesis, and Pharmacology
  作者：Navnath Gavande、Izumi Yamamoto、Noeris K. Salam、Tu-Hoa Ai、Peter M. Burden、Graham A. R. Johnston、Jane R. Hanrahan、Mary Chebib

  DOI：10.1021/ml1001344

  日期：2011.1.13

  Understanding the role of GABA(C) receptors in the central nervous system is limited due to a lack of specific ligands. Novel gamma-aminobutyric acid (GABA) analogues based on 3-(aminomethyl)-1-oxo-1-hydroxy-phospholane 17 and 3-(guanido)-1-oxo-1-hydroxy-phospholane 19 were investigated to obtain selective GABA(C) receptor antagonists. A compound of high potency (19, K-B = 10 mu M) and selectivity (greater than 100 times at rho(1) GABA(C) receptors as compared to alpha(1)beta(2)gamma(2L) GABA(A) and GABA(B(1b,2)) receptors) was obtained. The cyclic phosphinic acids (17 and 19) are novel lead agents for developing into more potent and selective GABA(C) receptor antagonists with increased lipophilicity for future in vivo studies.