2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeronitrile | 123283-25-0

• 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: 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeronitrile
• 英文别名: [4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl] methanesulfonate
• CAS: 123283-25-0
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: CNKQAAOQEYNFTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  85.62
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeronitrile 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 25.0~55.0 ℃ 、344.73 kPa 条件下， 反应 64.0h， 生成
  参考文献：
  名称：

  Studies on Ca2+ channel antagonists. A 2-diazo-3,3,3-trifluoropropionamide derivative related to verapamil as a potential photoaffinity probe

  摘要：

  2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-[N-[4-(N-methyl-2-diazo- 3,3,3-trifluoropropionamido)phenethyl]methyl-amino]valeronitril e (3), a potential photoaffinity probe for Ca2+ channels related to verapamil (1), was prepared from N-methyl-4-nitrophenethylamine (7) and 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeron itrile (12). Compound 3 showed concentration-dependent negative inotropic effects in rat right myocardial ventricular strips, EC50 = (1.05 +/- 0.33) X 10(-7) M (mean +/- SD), being slightly less potent than gallopamil (2), EC50 = (2.18 +/- 0.66) X 10(-8) M. It displaced [3H]gallopamil in myocardial membranes, Ki = (3.76 +/- 1.55) X 10(-8) M, compared to 2, Ki = (1.55 +/- 0.16) X 10(-8) M. Photoactivation at 265 nm reduced the recoverable binding of [3H]gallopamil to 26% compared to no effect on 2. This agent may be a useful photoaffinity probe to aid in further characterization of Ca2+ channels.

  DOI：

  10.1021/jm00164a064
• 作为产物：
  描述：

  (2S)-(-)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 、 甲基磺酰氯 、 三乙胺 、 二氯甲烷 生成 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeronitrile
  参考文献：
  名称：

  THEODORE, LOUIS J.;NELSON, WENDEL L., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 491-501

  摘要：

  DOI：

文献信息

• Iodination of verapamil for a stronger induction of death, through GSH efflux, of cancer cells overexpressing MRP1
  作者：Régis Barattin、Thomas Perrotton、Doriane Trompier、Doriane Lorendeau、Attilio Di Pietro、Amaury du Moulinet d’Hardemare、Hélène Baubichon-Cortay

  DOI：10.1016/j.bmc.2010.07.031

  日期：2010.9

  The multidrug resistance protein 1 (MRP1), involved in multidrug resistance (MDR) of cancer cells, was found to be modulated by verapamil, through stimulation of GSH transport, leading to apoptosis of MRP1-overexpressing cells. In this study, various iodinated derivatives of verapamil were synthesized, including iodination on the B ring, known to be involved in verapamil cardiotoxicity, and assayed for the stimulation of GSH efflux by MRP1. The iodination, for nearly all compounds, led to a higher stimulation of GSH efflux. However, determination of concomitant cytotoxicity is also important for selecting the best compound, which was found to be 10-fold more potent than verapamil. This will then allow us to design original anti-cancer compounds which could specifically kill the resistant cancer cells. (C) 2010 Published by Elsevier Ltd.