(1S)-1-amino-3-chloro-1-[(4-hydroxyphenyl)methyl]propan-2-one hydrochloride

• 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: (1S)-1-amino-3-chloro-1-[(4-hydroxyphenyl)methyl]propan-2-one hydrochloride
• 英文别名: H-TyrCH2Cl.HCl；(3S)-3-amino-1-chloro-4-(4-hydroxyphenyl)butan-2-one;hydrochloride
• 化学式: C₁₀H₁₂ClNO₂*ClH
• 分子量: 250.125
• InChiKey: LXSOTLKPNXAOOM-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-amino-3-chloro-1-[(4-hydroxyphenyl)methyl]propan-2-one hydrochloride 在 N-甲基吗啉 、 sodium iodide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 40.25h， 生成 (Z)-N-[(2S)-1-(4-hydroxyphenyl)-4-iodo-3-oxobutan-2-yl]octadec-9-enamide
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l
• 作为产物：
  描述：

  Boc-L-酪氨酸 在 盐酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 (1S)-1-amino-3-chloro-1-[(4-hydroxyphenyl)methyl]propan-2-one hydrochloride
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l

文献信息

• Method for preparing specific inhibitors of virus-specified proteases
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04644055A1

  公开（公告）日：1987-02-17

  A general method for preparing specific inhibitors of virus-specified proteases is disclosed. The inhibitors comprise a halomethyl ketone or methyl ketone moiety covalently linked to a peptide sequence of three, four or five amino acids or amino acid residues, which peptide sequence corresponds to an amino acid sequence found adjacent to and upstream of a cleavage site recognized by a virus-specified protease.

  揭示了一种制备病毒特异性蛋白酶特定抑制剂的通用方法。该抑制剂包括卤代甲基酮或甲基酮部分与三、四或五个氨基酸或氨基酸残基的肽序列共价连接，该肽序列与病毒特异性蛋白酶识别的切割位点相邻并上游的氨基酸序列相对应。
• Inhibition of cyclic nucleotide independent protein kinases
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04582821A1

  公开（公告）日：1986-04-15

  Peptide and amino acid halomethyl ketones are employed in processes for inhibiting cyclic nucleotide independent protein kinase activity and tumor cell growth.

  肽和氨基酸卤甲基酮被用于抑制循环核苷酸独立蛋白激酶活性和肿瘤细胞生长的过程中。
• Inhibition of viral protease activity by peptide halomethyl ketones
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04636492A1

  公开（公告）日：1987-01-13

  Selected tripeptide and tetrapeptide halomethyl ketones are employed in processes for treating viral infection in mammals. These compounds inhibit picornavirus protease activity.

  选定的三肽和四肽卤代甲基酮可用于治疗哺乳动物病毒感染的过程中。这些化合物抑制小肠病毒蛋白酶活性。