4-isopropyl-2-methoxy-1-nitrobenzene | 1368409-82-8

• 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: 4-isopropyl-2-methoxy-1-nitrobenzene
• 英文别名: 2-Methoxy-1-nitro-4-propan-2-ylbenzene
• CAS: 1368409-82-8
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: DHBAKLWZHRMGDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-isopropyl-2-methoxy-1-nitrobenzene 在 palladium 10% on activated carbon 、 对甲苯磺酸一水合物 、 氢气 、 potassium iodide 、 sodium nitrite 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 20.0 ℃ 、379.22 kPa 条件下， 反应 4.0h， 生成 1-iodo-4-isopropyl-2-methoxybenzene
  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：

  2-(3-甲氧基苯基)-2-丙醇 在 palladium 10% on activated carbon 、 甲酸铵 、 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 4-isopropyl-2-methoxy-1-nitrobenzene
  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

• ANTHELMINTIC AGENTS AND THEIR USE
  申请人：Chassaing Christophe Pierre Alain

  公开号：US20110319393A1

  公开（公告）日：2011-12-29

  This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.

  本发明涉及化合物和盐，通常可用作驱虫剂或作为制备驱虫剂的中间体。本发明还涉及制备这些化合物和盐的过程，包括这些化合物和盐的药物组合物和试剂盒，使用这些化合物和盐制备药物，并将这些化合物和盐用于治疗需要治疗的动物的治疗方法。
• USE OF ANTHELMINTIC AGENTS AGAINST DIROFILARIA IMMITIS
  申请人：INTERVET INTERNATIONAL B.V.

  公开号：US20170196854A1

  公开（公告）日：2017-07-13

  This invention is directed to compounds and salts that are generally useful as agents to treat an infection with Dirofilaria immitis . This invention also is directed to treatments comprising the administration of the compounds and salts to animals in need of the treatments.
• US9096524B2
  申请人：——

  公开号：US9096524B2

  公开（公告）日：2015-08-04
• [EN] INDOLE SULFONAMIDE MODULATORS OF PROGESTERONE RECEPTORS<br/>[FR] SULFAMIDE D'INDOLE MODULATEUR DE RÉCEPTEURS DE LA PROGESTÉRONE
  申请人：LILLY CO ELI

  公开号：WO2007087488A2

  公开（公告）日：2007-08-02

  (EN) Compounds of Formula (I), wherein n is 1 or 2, and R1, R2, R3, R4, R5, R6, R7, and R8 are as defined herein, their preparation, pharmaceutical compositions, and methods of use are disclosed.(FR) La présente invention concerne des composés de formule (I), dans laquelle: n et 1 ou 2, et R1, R2, R3, R4, R5, R6, R7, et R8 sont tels que définis dans la description, ainsi que leur préparation, leurs compositions pharmaceutiques, et leurs procédés d'utilisation.
• 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.