2-(2-chloro-benzylamino)-ethanol; hydrochloride | 75416-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-chloro-benzylamino)-ethanol; hydrochloride
• 英文别名: 2-(2-Chlor-benzylamino)-aethanol; Hydrochlorid；2-((2-Chlorobenzyl)amino)ethanol hydrochloride；2-[(2-chlorophenyl)methylamino]ethanol;hydrochloride
• CAS: 75416-45-4
• 化学式: C₉H₁₂ClNO*ClH
• 分子量: 222.114
• InChiKey: YMKPACQFPDUVHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-benzylamino)-ethanol; hydrochloride 在 三氯化铝 氯化铵 作用下， 反应 15.0h， 以60%的产率得到8-氯-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  分子内friedel-crafts烷基化。二。有效合成生物活性的1,2,3,4-四氢异喹啉

  摘要：

  提出了一种带有吸电子基团的四氢异喹啉的新合成方法。讨论了反应的范围和机理。这些四氢异喹啉中的许多是PNMT酶的有效抑制剂。

  DOI：

  10.1016/s0040-4039(00)92728-x
• 作为产物：
  描述：

  2-氯苯甲醛 、 C.I.酸性橙108 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 反应 28.5h， 以81%的产率得到2-(2-chloro-benzylamino)-ethanol; hydrochloride
  参考文献：
  名称：

  Synthesis and phospholipidosis effect of a series of cationic amphiphilic compounds: a case study to evaluate in silico and in vitro assays

  摘要：

  In recent years, a large number of in silico and in vitro assays have been developed for safety assessment in early drug discovery. These methods are usually validated using datasets of known drugs with large chemical diversity, while application to homologous series has been rarely explored. Here we report a case study about phospholipidosis (PLD) risk evaluation for a dataset of nine compounds, designed and synthesized to modulate the physico-chemical properties typical of cationic amphiphilic compounds (CADs), representing the main class of PLD inducers. Our aim was to investigate the effect of structure modification on PLD induction according to a number of standard in silico and in vitro methods. As a result, we found that different in silico methods lead to conflicting results when applied to our series of weak PLD inducers, thus the apparently easy-to-use definition of CADs requires special attention. Moreover, when weak inducers are tested in vitro, the revealed PLD effect may vary based on the purity grade of the tested compound and the features of the selected assay. Finally, we have shown that slight modifications on a chemical scaffold can have an impact on the PLD effect. This study also exemplifies that current in silico methods possibly overestimate the PLD induction effect of cationic amphiphilic compounds compared to the in vitro, with the risk of discarding promising compounds based on incorrect safety liabilities.

  DOI：

  10.1007/s00044-017-2093-5

文献信息

• Synthesis and phospholipidosis effect of a series of cationic amphiphilic compounds: a case study to evaluate in silico and in vitro assays
  作者：Susan Lepri、Aurora Valeri、Sandra Buratta、Martina Ceccarelli、Desirée Bartolini、Renzo Ruzziconi、Laura Goracci

  DOI：10.1007/s00044-017-2093-5

  日期：2018.2

  In recent years, a large number of in silico and in vitro assays have been developed for safety assessment in early drug discovery. These methods are usually validated using datasets of known drugs with large chemical diversity, while application to homologous series has been rarely explored. Here we report a case study about phospholipidosis (PLD) risk evaluation for a dataset of nine compounds, designed and synthesized to modulate the physico-chemical properties typical of cationic amphiphilic compounds (CADs), representing the main class of PLD inducers. Our aim was to investigate the effect of structure modification on PLD induction according to a number of standard in silico and in vitro methods. As a result, we found that different in silico methods lead to conflicting results when applied to our series of weak PLD inducers, thus the apparently easy-to-use definition of CADs requires special attention. Moreover, when weak inducers are tested in vitro, the revealed PLD effect may vary based on the purity grade of the tested compound and the features of the selected assay. Finally, we have shown that slight modifications on a chemical scaffold can have an impact on the PLD effect. This study also exemplifies that current in silico methods possibly overestimate the PLD induction effect of cationic amphiphilic compounds compared to the in vitro, with the risk of discarding promising compounds based on incorrect safety liabilities.
• Intramolecular friedel-crafts alkylations. II. An efficient synthesis of biologically active 1,2,3,4-tetrahydroisoquinolines
  作者：W.L. Mendelson、C.B. Spainhour、S.S. Jones、B.L. Lam、K.L. Wert

  DOI：10.1016/s0040-4039(00)92728-x

  日期：——

  A new synthesis of tetrahydroisoquinolines bearing electron withdrawing groups is presented. The scope and mechanism of the reaction are discussed. Many of these tetrahydroisoquinolines are potent inhibitors of the enzyme PNMT.

  提出了一种带有吸电子基团的四氢异喹啉的新合成方法。讨论了反应的范围和机理。这些四氢异喹啉中的许多是PNMT酶的有效抑制剂。