2-Amino-4'-benzyloxypropiophenone hydrochloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Amino-4'-benzyloxypropiophenone hydrochloride
• 英文别名: 2-amino-1-(4-phenylmethoxyphenyl)propan-1-one;hydrochloride
• 化学式: C₁₆H₁₇NO₂*ClH
• 分子量: 291.777
• InChiKey: PERFFJLYQMSLSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-4'-benzyloxypropiophenone hydrochloride 、 环己基异氰酸酯 在 三乙胺 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 以240 mg (55%)的产率得到5-(4'-Benzyloxyphenyl)-1-cyclohexyl-4-methyl-4-imidazolin-2-one
  参考文献：
  名称：

  4-imidazoline derivatives

  摘要：

  4-咪唑啉衍生物的化学式(I)和/或化学式(II)：其中R.sup.1代表C.sub.1 -C.sub.8烷基，C.sub.3 -C.sub.8烯基，C.sub.3 -C.sub.8炔基，C.sub.3 -C.sub.8环烷基，或者可选择地取代的芳基烷基；R.sup.2和R.sup.3独立地代表氢，C.sub.3 -C.sub.20烷基，C.sub.3 -C.sub.20烯基，C.sub.3 -C.sub.20炔基，C.sub.3 -C.sub.20烷氧基，C.sub.3 -C.sub.20烯氧基，C.sub.3 -C.sub.20炔氧基，C.sub.3 -C.sub.8环烷基，C.sub.1 -C.sub.10硫代烷基，或者可选择地取代的芳基烷基或芳基烷氧基；R.sup.4代表C.sub.1 -C.sub.6烷基，C.sub.3 -C.sub.8环烷基，或者可选择地取代的芳基烷基；但要求R.sup.2和R.sup.3不能同时为氢，以及其药学上可接受的盐。还提供了含有该化合物的药物配方。

  公开号：

  US05116858A1
• 作为产物：
  描述：

  4‘-苄氧基苯丙酮 在 盐酸 、 palladium on activated charcoal 、 氢气 、 溴 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 2-Amino-4'-benzyloxypropiophenone hydrochloride
  参考文献：
  名称：

  Toxicity of the amphetamine metabolites 4-hydroxyamphetamine and 4-hydroxynorephedrine in human dopaminergic differentiated SH-SY5Y cells

  摘要：

  Amphetamine (AMPH) is a psychostimulant used worldwide by millions of patients in the clinical treatment of attention deficit hyperactivity disorder, narcolepsy or even obesity, and is also a drug of abuse. 4-Hydroxynorephedrine (4-OHNE) and 4-hydroxyamphetamine (4-OHAMPH) are two major metabolites known to persist in the brain longer than AMPH. The contribution of AMPH metabolites for its neurotoxicity is undetermined.We evaluated the toxicity of AMPH and its metabolites 4-OHNE and 4-OHAMPH, obtained by chemical synthesis, in human dopaminergic differentiated SH-SY5Y neurons. Cells were exposed to AMPH (concentration range 0-5 mM) or 4-OHAMPH or 4-OHNE (concentration range 0-10 mM) for 24 or 48 h, and the viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MIT) and lactate dehydrogenase (LDH) leakage assays.Results showed that for both AMPH and the metabolites a concentration-dependent toxicity was observed. The toxic concentration 50% (TC50) for AMPH and 4-OHNE following 24 h exposure was circa 3.5 mM and 8 mM, respectively. For 4-OHAMPH the TC50 was not reached in the tested concentration range. N-acetyl cysteine, cycloheximide, L-carnitine, and methylphenidate were able to reduce cell death induced by AMPH TC50. Acridine orange/ethidium bromide staining showed evident signs of late apoptotic cells and necrotic cells following 24 h exposure to AMPH 3.50 mM. The 4-OHAMPH metabolite at 8.00 mM originated few late apoptotic cells, whereas 4-OHNE at 8.00 mM resulted in late apoptotic cells and necrotic cells, in a scenario similar to AMPH.In conclusion, the AMPH metabolite 4-OHNE is more toxic than 4-OHAMPH, nonetheless both are less toxic than the parent compound in vitro. The most toxic metabolite 4-OHNE has longer permanence in the brain, rendering likely its contribution for AMPH neurotoxicity. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.toxlet.2017.01.012

文献信息

• 4-Imidazoline derivatives and their use in preparing pharmaceutical compositions
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0396973A1

  公开（公告）日：1990-11-14

  4-lmidazoline derivatives represented by the formula (I) and/or formula (II): wherein R1 represents C1-C8 alkyl, C3-C8 alkenyl, C3-Cs alkynyl, C3-C8 cycloalkyl, or optionally substituted aralkyl; R2 and R3 independently represent hydrogen, C3-C20 alkyl, C3-C20 alkenyl, C3-C20 alkynyl, C3-C20 alkoxy, C3-C20 alkenyloxy, C3-C20 alkynyloxy, C3-CS cycloalkyl, C1-C10 alkylthio, or optionally substituted aralkyl or aralkyloxy; R4 represents C1-C6 alkyl, C3-C8 cycloalkyl, or optionally substituted aralkyl; provided that R2 and R3 cannot be hydrogen at the same time, and pharmaceutically acceptable salts thereof. A pharmaceutical formulation containing the compound is also provided.

  由式 (I) 和/或式 (II) 代表的 4-咪唑啉衍生物： 其中 R1 代表 C1-C8 烷基、C3-C8 烯基、C3-Cs 炔基、C3-C8 环烷基或任选取代的芳烷基；R2 和 R3 独立地代表氢、C3-C20 烷基、C3-C20 烯基、C3-C20 炔基、C3-C20 烷氧基、C3-C20 烯氧基、C3-C20 炔氧基、C3-CS 环烷基、C1-C10 硫代烷基或任选取代的芳烷基或芳烷氧基； R4 代表 C1-C6 烷基、C3-C8 环烷基或任选取代的芳烷基；但 R2 和 R3 不能同时为氢，以及其药学上可接受的盐。 还提供了含有该化合物的药物制剂。
• 5-Aryl-imidazolin-2-ones as a scaffold for potent antioxidant and memory-improving activity
  作者：Kazutoshi Watanabe、Yasuhiro Morinaka、Yoshio Hayashi、Masaki Shinoda、Hiroyoshi Nishi、Nobuko Fukushima、Toshiaki Watanabe、Akira Ishibashi、Satoshi Yuki、Masahiko Tanaka

  DOI：10.1016/j.bmcl.2007.12.064

  日期：2008.2

  A series of 5-phenyl-substituted-N-alkyl-imidazolin-2-ones with potent radical-scavenging activity and lipid peroxidation inhibitory activity was synthesized. Many of the compounds showed memory-improving effect in animal models independent of the inhibitory activity on lipid peroxidation. (c) 2008 Elsevier Ltd. All rights reserved.
• US5116858A
  申请人：——

  公开号：US5116858A

  公开（公告）日：1992-05-26
• 4-imidazoline derivatives
  申请人：Mitsubishi Kasei Corporation

  公开号：US05116858A1

  公开（公告）日：1992-05-26

  4-Imidazoline derivatives represented by the formula (I) and/or formula (II): ##STR1## wherein R.sup.1 represents C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, or optionally substituted aralkyl; R.sup.2 and R.sup.3 independently represent hydrogen, C.sub.3 -C.sub.20 alkyl, C.sub.3 -C.sub.20 alkenyl, C.sub.3 -C.sub.20 alkynyl, C.sub.3 -C.sub.20 alkoxy, C.sub.3 -C.sub.20 alkenyloxy, C.sub.3 -C.sub.20 alkynyloxy, C.sub.3 -C.sub.8 cyloalkyl, C.sub.1 -C.sub.10 alkylthio, or optionally substituted aralkyl or aralkyloxy; R.sup.4 represents C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or optionally substituted aralkyl; provided that R.sup.2 and R.sup.3 cannot be hydrogen at the same time, and pharmaceutically acceptable salts thereof. A pharmaceutical formulation containing the compound is also provided.

  4-咪唑啉衍生物的化学式(I)和/或化学式(II)：其中R.sup.1代表C.sub.1 -C.sub.8烷基，C.sub.3 -C.sub.8烯基，C.sub.3 -C.sub.8炔基，C.sub.3 -C.sub.8环烷基，或者可选择地取代的芳基烷基；R.sup.2和R.sup.3独立地代表氢，C.sub.3 -C.sub.20烷基，C.sub.3 -C.sub.20烯基，C.sub.3 -C.sub.20炔基，C.sub.3 -C.sub.20烷氧基，C.sub.3 -C.sub.20烯氧基，C.sub.3 -C.sub.20炔氧基，C.sub.3 -C.sub.8环烷基，C.sub.1 -C.sub.10硫代烷基，或者可选择地取代的芳基烷基或芳基烷氧基；R.sup.4代表C.sub.1 -C.sub.6烷基，C.sub.3 -C.sub.8环烷基，或者可选择地取代的芳基烷基；但要求R.sup.2和R.sup.3不能同时为氢，以及其药学上可接受的盐。还提供了含有该化合物的药物配方。
• Toxicity of the amphetamine metabolites 4-hydroxyamphetamine and 4-hydroxynorephedrine in human dopaminergic differentiated SH-SY5Y cells
  作者：R. Feio-Azevedo、V.M. Costa、L.M. Ferreira、P.S. Branco、F.C. Pereira、M.L. Bastos、F. Carvalho、J.P. Capela

  DOI：10.1016/j.toxlet.2017.01.012

  日期：2017.3

  Amphetamine (AMPH) is a psychostimulant used worldwide by millions of patients in the clinical treatment of attention deficit hyperactivity disorder, narcolepsy or even obesity, and is also a drug of abuse. 4-Hydroxynorephedrine (4-OHNE) and 4-hydroxyamphetamine (4-OHAMPH) are two major metabolites known to persist in the brain longer than AMPH. The contribution of AMPH metabolites for its neurotoxicity is undetermined.We evaluated the toxicity of AMPH and its metabolites 4-OHNE and 4-OHAMPH, obtained by chemical synthesis, in human dopaminergic differentiated SH-SY5Y neurons. Cells were exposed to AMPH (concentration range 0-5 mM) or 4-OHAMPH or 4-OHNE (concentration range 0-10 mM) for 24 or 48 h, and the viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MIT) and lactate dehydrogenase (LDH) leakage assays.Results showed that for both AMPH and the metabolites a concentration-dependent toxicity was observed. The toxic concentration 50% (TC50) for AMPH and 4-OHNE following 24 h exposure was circa 3.5 mM and 8 mM, respectively. For 4-OHAMPH the TC50 was not reached in the tested concentration range. N-acetyl cysteine, cycloheximide, L-carnitine, and methylphenidate were able to reduce cell death induced by AMPH TC50. Acridine orange/ethidium bromide staining showed evident signs of late apoptotic cells and necrotic cells following 24 h exposure to AMPH 3.50 mM. The 4-OHAMPH metabolite at 8.00 mM originated few late apoptotic cells, whereas 4-OHNE at 8.00 mM resulted in late apoptotic cells and necrotic cells, in a scenario similar to AMPH.In conclusion, the AMPH metabolite 4-OHNE is more toxic than 4-OHAMPH, nonetheless both are less toxic than the parent compound in vitro. The most toxic metabolite 4-OHNE has longer permanence in the brain, rendering likely its contribution for AMPH neurotoxicity. (C) 2017 Elsevier B.V. All rights reserved.