N¹-(4-methoxyphenyl)ethane-1,2-diamine hydrochloride | 143745-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N¹-(4-methoxyphenyl)ethane-1,2-diamine hydrochloride
• 英文别名: N1-(4-methoxyphenyl)ethane-1,2-diamine hydrochloride；N'-(4-methoxyphenyl)ethane-1,2-diamine;hydrochloride
• CAS: 143745-54-4
• 化学式: C₉H₁₄N₂O*ClH
• 分子量: 202.684
• InChiKey: QSCNYWPYBBJPHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 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：
  47.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-(4-methoxyphenyl)ethane-1,2-diamine hydrochloride 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (S)-2-amino-N-(2-((4-methoxyphenyl)amino)ethyl)-4-methylpentanamide
  参考文献：
  名称：

  Arylaminoethyl amides as inhibitors of the cysteine protease cathepsin K—investigating P1′ substituents

  摘要：

  Modeling, synthesis and in vitro activities of a series of arylaminoethyl amide based inhibitors of the cysteine protease cathepsin K are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00344-5
• 作为产物：
  描述：

  tert-butyl (2-((4-methoxyphenyl)amino)ethyl)carbamate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以77%的产率得到N¹-(4-methoxyphenyl)ethane-1,2-diamine hydrochloride
  参考文献：
  名称：

  Discovery and Development of First-in-Class ACKR3/CXCR7 Superagonists for Platelet Degranulation Modulation

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c01198

文献信息

• Arylaminoethyl Amides as Novel Non-Covalent Cathepsin K Inhibitors
  作者：Eva Altmann、Johanne Renaud、Jonathan Green、David Farley、Brian Cutting、Wolfgang Jahnke

  DOI：10.1021/jm010801s

  日期：2002.6.1

  A series of N-alpha-benzyloxycarbonyl- and N-alpha-acyl-L-leucine(2-phenylaminoethyl)amide derivatives were prepared and evaluated for their inhibitory activity against rabbit and human cysteine proteases cathepsins K, L, and S. These data indicate that N-alpha-acyl-alpha-amino acid-(arylaminoethyl)amides represent a new class of selective non-covalent inhibitors of cathepsin K. Compounds 4b, 4e, and 4g exhibit high potency toward rabbit and human cathepsin K (IC50 < 0.006 muM) and are characterized by an excellent selectivity profile vs human cathepsins L and S.
• Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1<i>H</i>-Imidazoles
  作者：Thomas Wiglenda、Ronald Gust

  DOI：10.1021/jm061106t

  日期：2007.4.1

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.