2-[4-(2-氨基乙基)-苯氧基]-N,N-二乙基乙酰胺 | 133025-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-(2-氨基乙基)-苯氧基]-N,N-二乙基乙酰胺
• 英文名称: N,N-diethyl-2-(4-(2-aminoethyl)phenoxy)acetamide
• 英文别名: 2-[4-(2-Amino-ethyl)-phenoxy]-N,N-diethyl-acetamide；2-[4-(2-aminoethyl)phenoxy]-N,N-diethylacetamide
• CAS: 133025-92-0
• 化学式: C₁₄H₂₂N₂O₂
• mdl: MFCD04114529
• 分子量: 250.341
• InChiKey: RULDHHMNJXAYGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(2-氨基乙基)-苯氧基]-N,N-二乙基乙酰胺 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以66%的产率得到N,N-diethyl-2-(4-(2-aminoethyl)phenoxy)ethylamine
  参考文献：
  名称：

  Structure−Activity Relationship of N-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists

  摘要：

  A novel series of N-(phenylalkyl)cinnamides related to N-(4-phenylbutyl)-3,4-dihydroxy-beta-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N-(phenylalkyl)cinnamides are selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and >1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. Potency at alpha(1) adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1A/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.

  DOI：

  10.1021/jm990199u
• 作为产物：
  描述：

  N,N-diethyl-2-(4-(2-N-benzyloxycarbamyllethyl)phenoxy)acetamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以93%的产率得到2-[4-(2-氨基乙基)-苯氧基]-N,N-二乙基乙酰胺
  参考文献：
  名称：

  Structure−Activity Relationship of N-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists

  摘要：

  A novel series of N-(phenylalkyl)cinnamides related to N-(4-phenylbutyl)-3,4-dihydroxy-beta-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N-(phenylalkyl)cinnamides are selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and >1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. Potency at alpha(1) adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1A/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.

  DOI：

  10.1021/jm990199u

文献信息

• 2-Hydroxy-3-thienyloxypropylamino derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0386920A2

  公开（公告）日：1990-09-12

  2-Hydroxy-3-thienyloxypropylamino compounds are described as useful in the treatment of obesity and related conditions. Processes for their preparation are described, as are novel intermediates and pharmaceutical compositions containing them.

  2-Hydroxy-3-thienyloxypropylamino compounds is described as useful in the treatment of obesity and related conditions.介绍了其制备工艺，以及含有这些化合物的新型中间体和药物组合物。
• Structure−Activity Relationship of <i>N</i>-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists
  作者：Amir P. Tamiz、Sui Xiong Cai、Zhang-Lin Zhou、Po-Wai Yuen、Robert M. Schelkun、Edward R. Whittemore、Eckard Weber、Richard M. Woodward、John F. W. Keana

  DOI：10.1021/jm990199u

  日期：1999.8.1

  A novel series of N-(phenylalkyl)cinnamides related to N-(4-phenylbutyl)-3,4-dihydroxy-beta-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N-(phenylalkyl)cinnamides are selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and >1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. Potency at alpha(1) adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1A/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.