4-(3,4-二甲氧基苯基)-N-[2-(3,4-二甲氧基苯基)乙基]-4-(异硫氰酸基甲基)-N,5-二甲基己烷-1-胺 | 102852-53-9

• 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: 4-(3,4-二甲氧基苯基)-N-[2-(3,4-二甲氧基苯基)乙基]-4-(异硫氰酸基甲基)-N,5-二甲基己烷-1-胺
• 英文名称: (+/-)-5-<(3,4-dimethoxyphenethyl)methylamino>-2-(3,4-dimethoxyphenyl)-2-isopropylpentyl isothiocyanate
• 英文别名: 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentyl isothiocyanate；4-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(isothiocyanatomethyl)-N,5-dimethylhexan-1-amine
• CAS: 102852-53-9
• 化学式: C₂₈H₄₀N₂O₄S
• 分子量: 500.703
• InChiKey: ZPHLZPWMGNFCCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  盐酸维拉帕米 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 23.5h， 生成 4-(3,4-二甲氧基苯基)-N-[2-(3,4-二甲氧基苯基)乙基]-4-(异硫氰酸基甲基)-N,5-二甲基己烷-1-胺
  参考文献：
  名称：

  Studies on calcium(2+) channel antagonists. 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylpentyl isothiocyanate, a chemoaffinity ligand derived from verapamil

  摘要：

  Reduction of 1 (verapamil) afforded amine 2, which was converted with thiophosgene to isothiocyanate 3, a chemoaffinity ligand for Ca2+ channels. Compound 3 showed concentration-dependent negative inotropic effects in rat right myocardial ventricular strips, EC50 = (4.56 +/- 3.40) X 10(-6) M (mean +/- SD), being slightly less potent than 4 (gallopamil), EC50 = (1.95 +/- 1.22) X 10(-6) M. It displaced [3H]gallopamil in rat myocardial membranes, IC50 = (3.42 +/- 2.51) X 10(-7) M, approximately equipotent with 1. It showed irreversible antagonism of [3H]gallopamil binding when preincubated at 10(-5) M; only 25% of [3H]gallopamil binding vs. control was observed. This agent may be a useful chemoaffinity ligand to aid in characterization of Ca2+ channels.

  DOI：

  10.1021/jm00159a040

文献信息

• THEODORE L. J.; NELSON W. L.; ZOBRIST R. H.; GIACOMINI K. M.; GIACOMINI J+, J. MED. CHEM., 29,(1986) N 9, 1789-1792
  作者：THEODORE L. J.、 NELSON W. L.、 ZOBRIST R. H.、 GIACOMINI K. M.、 GIACOMINI J+

  DOI：——

  日期：——
• Studies on calcium(2+) channel antagonists. 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylpentyl isothiocyanate, a chemoaffinity ligand derived from verapamil
  作者：Louis J. Theodore、Wendel L. Nelson、Ray H. Zobrist、Kathleen M. Giacomini、John C. Giacomini

  DOI：10.1021/jm00159a040

  日期：1986.9

  Reduction of 1 (verapamil) afforded amine 2, which was converted with thiophosgene to isothiocyanate 3, a chemoaffinity ligand for Ca2+ channels. Compound 3 showed concentration-dependent negative inotropic effects in rat right myocardial ventricular strips, EC50 = (4.56 +/- 3.40) X 10(-6) M (mean +/- SD), being slightly less potent than 4 (gallopamil), EC50 = (1.95 +/- 1.22) X 10(-6) M. It displaced [3H]gallopamil in rat myocardial membranes, IC50 = (3.42 +/- 2.51) X 10(-7) M, approximately equipotent with 1. It showed irreversible antagonism of [3H]gallopamil binding when preincubated at 10(-5) M; only 25% of [3H]gallopamil binding vs. control was observed. This agent may be a useful chemoaffinity ligand to aid in characterization of Ca2+ channels.