(S)-1-chloro-3-(naphthalen-2-ylamino)propan-2-ol | 1303526-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-chloro-3-(naphthalen-2-ylamino)propan-2-ol
• CAS: 1303526-29-5
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: BBOKVLOSJUQSSC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-萘胺 、 环氧氯丙烷 在 磷脂酶B 作用下， 以 异丙醚 为溶剂， 反应 8.0h， 生成 (S)-1-chloro-3-(naphthalen-2-ylamino)propan-2-ol 、
  参考文献：
  名称：

  Selective biocatalytic aminolysis of (±)-epichlorohydrin: Synthesis and ICAM-1 inhibitory activity of (S)-(+)-3-arylamino-1-chloropropan-2-ols

  摘要：

  Regio-and enantioselective synthesis of (S)-(+)-3-arylamino-1-chloropropan-2-ols has been achieved by the epoxide ring opening of (+/-)-epichlorohydrin with different aromatic amines in the presence of Candida rugosa lipase. Activities of seven model (S)-(+)-3-arylamino-1-chloropropan-2-ols, out of 10 compounds synthesized, have been evaluated for the inhibition of tumor necrosis factor-alpha TNF-alpha) induced expression of intercellular adhesion molecule-1 (ICAM-1), which is one of the factors responsible for the modulation of inflammation in biological systems; (S)-(+)-1-chloro-3-(2'-chlorophenylamino)-propan-2-ol has been found to exhibit highest activity, that is, 86% inhibition of TNF-alpha induced expression of ICAM-1 at a concentration of 40 mu g/ml. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.029