(1S,2R,3R)-3-aminocyclohexane-1,2-diol hydrochloride | 1414856-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R)-3-aminocyclohexane-1,2-diol hydrochloride
• 英文别名: (1S,2R,3R)-3-aminocyclohexane-1,2-diol;hydrochloride
• CAS: 1414856-66-8
• 化学式: C₆H₁₃NO₂*ClH
• 分子量: 167.636
• InChiKey: MIDIYKXNTKNGBP-KJESCUSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴环己烯 在 盐酸 、 甲基磺酰胺 、 AD-mix β 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 126.0h， 生成 (1S,2R,3R)-3-aminocyclohexane-1,2-diol hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of selective and potent cyclin-dependent kinase inhibitors

  摘要：

  A new series of 2,6,9-trisubstituted purines, structurally related to the cyclin-dependent kinase (CDK) inhibitor Roscovitine, has been synthesized. These compounds mainly differ by the substituent on the C-2 position which encompasses a diol group. These compounds were screened for kinase inhibitory activities and antiproliferative effects. They were shown to be potent inhibitors of cyclin-dependent kinases but also, for some of them of casein kinase 1 (CK1) and dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A). The inhibition of kinases was accompanied by an antiproliferative effect against several tumor cell-lines. The most potent derivatives inhibited SH-SY5Y (neuroblastoma) tumor cell line with an IC50 < 0.5 mu M which means approximately a 30 fold increase compared to Roscovitine. A valine ester was also prepared from the most potent inhibitor to serve as a prodrug. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.033