Tributyl-(6-cyclopropylpyridin-2-yl)stannane | 1163693-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Tributyl-(6-cyclopropylpyridin-2-yl)stannane
• CAS: 1163693-16-0
• 化学式: C₂₀H₃₅NSn
• 分子量: 408.215
• InChiKey: QVUCDUTWRFAPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-methyl-cyclopropanecarboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide 、 Tributyl-(6-cyclopropylpyridin-2-yl)stannane 在 二(三叔丁基膦)钯 、 盐酸 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙酸乙酯 为溶剂， 生成 (1R,2R)-2-methylcyclopropanecarboxylic acid [4-(6-cyclopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl]amide hydrochloride
  参考文献：
  名称：

  Discovery of (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide, a potent and orally efficacious mGlu5 receptor negative allosteric modulator

  摘要：

  A novel series of selective negative allosteric modulators (NAMs) for metabotropic glutamate receptor 5 (mGlu5) was discovered from an isothiazole scaffold. One compound of this series, (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide (24), demonstrated satisfactory pharmacokinetic properties and, following oral dosing in rats, produced dose-dependent and long-lasting mGlu5 receptor occupancy. Consistent with the hypothesis that blockade of mGlu5 receptors will produce analgesic effects in mammals, compound 24 produced a dose-dependent reduction in paw licking responses in the formalin model of persistent pain. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.009

文献信息

• Discovery of (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide, a potent and orally efficacious mGlu5 receptor negative allosteric modulator
  作者：Junliang Hao、Veronique Dehlinger、Adam M. Fivush、Helene C.E. Rudyk、Thomas C. Britton、Sean P. Hollinshead、Benjamin P. Vokits、Barry P. Clark、Steven S. Henry、Steven M. Massey、Langu Peng、Bruce A. Dressman、Beverly A. Heinz、Edda F. Roberts、Mallorie R. Bracey-Walker、Steven Swanson、John T. Catlow、Patrick L. Love、Anita D. Tepool、Steven C. Peters、Rosa Maria A. Simmons、Smriti Iyengar、David L. McKinzie、James A. Monn

  DOI：10.1016/j.bmcl.2013.01.009

  日期：2013.3

  A novel series of selective negative allosteric modulators (NAMs) for metabotropic glutamate receptor 5 (mGlu5) was discovered from an isothiazole scaffold. One compound of this series, (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide (24), demonstrated satisfactory pharmacokinetic properties and, following oral dosing in rats, produced dose-dependent and long-lasting mGlu5 receptor occupancy. Consistent with the hypothesis that blockade of mGlu5 receptors will produce analgesic effects in mammals, compound 24 produced a dose-dependent reduction in paw licking responses in the formalin model of persistent pain. (c) 2013 Elsevier Ltd. All rights reserved.