2-isopropyl-4,5-dimethoxybenzyl methanesulfonate | 1448464-65-0

• 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-isopropyl-4,5-dimethoxybenzyl methanesulfonate
• 英文别名: (4,5-Dimethoxy-2-propan-2-ylphenyl)methyl methanesulfonate；(4,5-dimethoxy-2-propan-2-ylphenyl)methyl methanesulfonate
• CAS: 1448464-65-0
• 化学式: C₁₃H₂₀O₅S
• 分子量: 288.365
• InChiKey: GGNAGRATWPFWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-isopropyl-4,5-dimethoxybenzyl methanesulfonate 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 9-(2-isopropyl-4,5-dimethoxybenzyl)-N⁶-methyl-9H-purine-2,6-diamine
  参考文献：
  名称：

  Evaluation of adenine as scaffold for the development of novel P2X3 receptor antagonists

  摘要：

  Ligands that selectively block P2X3 receptors localized on nociceptive sensory fibres may be useful for the treatment of chronic pain conditions including neuropathic pain, migraine, and inflammatory pain. With the aim at exploring the suitability of adenine moiety as a scaffold for the development of antagonists of this receptor, a series of 9-benzyl-2-aminoadenine derivatives were designed and synthesized. These new compounds were functionally evaluated at rat or human P2X3 receptors expressed in human embryonic kidney (HEK) cells and on native P2X3 receptors from mouse trigeminal ganglion sensory neurons using patch clamp recording under voltage clamp configuration. The new molecules behaved as P2X3 antagonists, as they rapidly and reversibly inhibited (IC50 in the low micromolar range) the membrane currents induced via P2X3 receptor activation by the full agonist alpha,beta-methyleneATP. Introduction of a small lipophilic methyl substituent at the 6-amino group enhanced the activity, in comparison to the corresponding unsubstituted derivative, resulting in the 9-(5-iodo-2-isopropyl-4-methoxybenzyl)-N-6-methyl-9H-purine-2,6-diamine (24), which appears to be a good antagonist on recombinant and native P2X3 receptors with IC50 = 1.74 +/- 0.21 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.037
• 作为产物：
  描述：

  3,4-dimethoxy-(1'-hydroxy-1'-methylethyl)benzene 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 甲酸铵 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 2-isopropyl-4,5-dimethoxybenzyl methanesulfonate
  参考文献：
  名称：

  Evaluation of adenine as scaffold for the development of novel P2X3 receptor antagonists

  摘要：

  Ligands that selectively block P2X3 receptors localized on nociceptive sensory fibres may be useful for the treatment of chronic pain conditions including neuropathic pain, migraine, and inflammatory pain. With the aim at exploring the suitability of adenine moiety as a scaffold for the development of antagonists of this receptor, a series of 9-benzyl-2-aminoadenine derivatives were designed and synthesized. These new compounds were functionally evaluated at rat or human P2X3 receptors expressed in human embryonic kidney (HEK) cells and on native P2X3 receptors from mouse trigeminal ganglion sensory neurons using patch clamp recording under voltage clamp configuration. The new molecules behaved as P2X3 antagonists, as they rapidly and reversibly inhibited (IC50 in the low micromolar range) the membrane currents induced via P2X3 receptor activation by the full agonist alpha,beta-methyleneATP. Introduction of a small lipophilic methyl substituent at the 6-amino group enhanced the activity, in comparison to the corresponding unsubstituted derivative, resulting in the 9-(5-iodo-2-isopropyl-4-methoxybenzyl)-N-6-methyl-9H-purine-2,6-diamine (24), which appears to be a good antagonist on recombinant and native P2X3 receptors with IC50 = 1.74 +/- 0.21 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.037

文献信息

• Evaluation of adenine as scaffold for the development of novel P2X3 receptor antagonists
  作者：Catia Lambertucci、Mayya Sundukova、Dhuldeo D. Kachare、Deepak S. Panmand、Diego Dal Ben、Michela Buccioni、Gabriella Marucci、Anna Marchenkova、Ajiroghene Thomas、Andrea Nistri、Gloria Cristalli、Rosaria Volpini

  DOI：10.1016/j.ejmech.2013.04.037

  日期：2013.7

  Ligands that selectively block P2X3 receptors localized on nociceptive sensory fibres may be useful for the treatment of chronic pain conditions including neuropathic pain, migraine, and inflammatory pain. With the aim at exploring the suitability of adenine moiety as a scaffold for the development of antagonists of this receptor, a series of 9-benzyl-2-aminoadenine derivatives were designed and synthesized. These new compounds were functionally evaluated at rat or human P2X3 receptors expressed in human embryonic kidney (HEK) cells and on native P2X3 receptors from mouse trigeminal ganglion sensory neurons using patch clamp recording under voltage clamp configuration. The new molecules behaved as P2X3 antagonists, as they rapidly and reversibly inhibited (IC50 in the low micromolar range) the membrane currents induced via P2X3 receptor activation by the full agonist alpha,beta-methyleneATP. Introduction of a small lipophilic methyl substituent at the 6-amino group enhanced the activity, in comparison to the corresponding unsubstituted derivative, resulting in the 9-(5-iodo-2-isopropyl-4-methoxybenzyl)-N-6-methyl-9H-purine-2,6-diamine (24), which appears to be a good antagonist on recombinant and native P2X3 receptors with IC50 = 1.74 +/- 0.21 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.