1-(2-Nitropropenyl)-3,7,8,9-tetrahydro-pyrano[3,2-e]indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(2-Nitropropenyl)-3,7,8,9-tetrahydro-pyrano[3,2-e]indole
• 英文别名: 1-[(E)-2-nitroprop-1-enyl]-3,7,8,9-tetrahydropyrano[3,2-e]indole
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: QHRZANVRJMLVHW-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Nitropropenyl)-3,7,8,9-tetrahydro-pyrano[3,2-e]indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-methyl-2-(3,7,8,9-tetrahydro-pyrano[3,2-e]indol-1-yl)-ethylamine
  参考文献：
  名称：

  A Novel and Selective 5-HT₂ Receptor Agonist with Ocular Hypotensive Activity:  (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole

  摘要：

  Serotonin 5-HT2 receptor agonists have recently been shown to be effective, in lowering intraocular pressure in nonhuman primates and represent a potential new class of antiglaucoma agents. As part of an effort to identify new selective agonists at this receptor, we have found that (S)-(+)-l-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole (AL-37350A, 11) has high affinity and selectivity (> 1000-fold) for the 5-HT2 receptor relative to other 5-HT receptors. More specifically, 11 is a potent agonist at the 5-HT2A receptor (EC50 = 28.6 nM, E-max = 103%) that is comparable to serotonin. Evaluation of 11 in conscious ocular hypertensive cynomolgus monkeys showed this compound to be efficacious in reducing intraocular pressure (13.1 mmHg, -37%). Thus, 11 is a potent full agonist with selectivity for the 5-HT2 receptor and is anticipated to serve as a useful tool in exploring the role of the 5-HT2 receptor and its effector system in controlling intraocular pressure.

  DOI：

  10.1021/jm030205t
• 作为产物：
  描述：

  硝基乙烷 、 8,9-dihydropyrano<3,2-e>indole-1-carboxaldehyde 在 ammonium acetate 作用下， 反应 3.0h， 以82%的产率得到1-(2-Nitropropenyl)-3,7,8,9-tetrahydro-pyrano[3,2-e]indole
  参考文献：
  名称：

  A Novel and Selective 5-HT₂ Receptor Agonist with Ocular Hypotensive Activity:  (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole

  摘要：

  Serotonin 5-HT2 receptor agonists have recently been shown to be effective, in lowering intraocular pressure in nonhuman primates and represent a potential new class of antiglaucoma agents. As part of an effort to identify new selective agonists at this receptor, we have found that (S)-(+)-l-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole (AL-37350A, 11) has high affinity and selectivity (> 1000-fold) for the 5-HT2 receptor relative to other 5-HT receptors. More specifically, 11 is a potent agonist at the 5-HT2A receptor (EC50 = 28.6 nM, E-max = 103%) that is comparable to serotonin. Evaluation of 11 in conscious ocular hypertensive cynomolgus monkeys showed this compound to be efficacious in reducing intraocular pressure (13.1 mmHg, -37%). Thus, 11 is a potent full agonist with selectivity for the 5-HT2 receptor and is anticipated to serve as a useful tool in exploring the role of the 5-HT2 receptor and its effector system in controlling intraocular pressure.

  DOI：

  10.1021/jm030205t

文献信息

• PYRANOINDOLES FOR TREATING GLAUCOMA
  申请人：ALCON, INC.

  公开号：EP1268482B1

  公开（公告）日：2003-09-24
• US7012090B1
  申请人：——

  公开号：US7012090B1

  公开（公告）日：2006-03-14
• A Novel and Selective 5-HT₂ Receptor Agonist with Ocular Hypotensive Activity:  (<i>S</i>)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-<i>e</i>]indole
  作者：Jesse A. May、Hwang-Hsing Chen、Andrew Rusinko、Vincent M. Lynch、Najam A. Sharif、Marsha A. McLaughlin

  DOI：10.1021/jm030205t

  日期：2003.9.1

  Serotonin 5-HT2 receptor agonists have recently been shown to be effective, in lowering intraocular pressure in nonhuman primates and represent a potential new class of antiglaucoma agents. As part of an effort to identify new selective agonists at this receptor, we have found that (S)-(+)-l-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole (AL-37350A, 11) has high affinity and selectivity (> 1000-fold) for the 5-HT2 receptor relative to other 5-HT receptors. More specifically, 11 is a potent agonist at the 5-HT2A receptor (EC50 = 28.6 nM, E-max = 103%) that is comparable to serotonin. Evaluation of 11 in conscious ocular hypertensive cynomolgus monkeys showed this compound to be efficacious in reducing intraocular pressure (13.1 mmHg, -37%). Thus, 11 is a potent full agonist with selectivity for the 5-HT2 receptor and is anticipated to serve as a useful tool in exploring the role of the 5-HT2 receptor and its effector system in controlling intraocular pressure.