3-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-(tert-butyldimethylsilyloxy)-1H-indol-1-yl)propanoic acid | 1417416-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-(tert-butyldimethylsilyloxy)-1H-indol-1-yl)propanoic acid
• 英文别名: 3-[5-[Tert-butyl(dimethyl)silyl]oxy-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]indol-1-yl]propanoic acid；3-[5-[tert-butyl(dimethyl)silyl]oxy-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]indol-1-yl]propanoic acid
• CAS: 1417416-65-9
• 化学式: C₂₄H₃₈N₂O₅Si
• 分子量: 462.662
• InChiKey: OITSOZHCUYKCRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((N-(5-aminopentyl)amino)carbonyl)tetramethylrhodamine 、 3-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-(tert-butyldimethylsilyloxy)-1H-indol-1-yl)propanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Near native binding of a fluorescent serotonin conjugate to serotonin type 3 receptors

  摘要：

  Described is the synthesis of 5-hydroxytryptamine-tetramethylrhodamine (5HT*); an indole nitrogen linked fluorescent conjugate of serotonin. Through a series fluorescence quenching experiments and experiments in the presence of a known competitive antagonist (Granisetron), it was shown that 5HT* specifically binds to purified homo-pentameric type-3 human serotonin receptors (5HT(3A)). The measured dissociation constant and Hill coefficient are K-d = 83 +/- 3 nM and n = 3.1 +/- 0.3, respectively which is indicative of multi-ligand binding and cooperativity similar to that of unconjugated serotonin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.082
• 作为产物：
  描述：

  5-羟基色胺盐酸盐 在 咪唑 、 水 、 苄基三甲基氢氧化铵 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 3-(3-(2-(tert-butoxycarbonylamino)ethyl)-5-(tert-butyldimethylsilyloxy)-1H-indol-1-yl)propanoic acid
  参考文献：
  名称：

  Near native binding of a fluorescent serotonin conjugate to serotonin type 3 receptors

  摘要：

  Described is the synthesis of 5-hydroxytryptamine-tetramethylrhodamine (5HT*); an indole nitrogen linked fluorescent conjugate of serotonin. Through a series fluorescence quenching experiments and experiments in the presence of a known competitive antagonist (Granisetron), it was shown that 5HT* specifically binds to purified homo-pentameric type-3 human serotonin receptors (5HT(3A)). The measured dissociation constant and Hill coefficient are K-d = 83 +/- 3 nM and n = 3.1 +/- 0.3, respectively which is indicative of multi-ligand binding and cooperativity similar to that of unconjugated serotonin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.082

文献信息

• Near native binding of a fluorescent serotonin conjugate to serotonin type 3 receptors
  作者：Elsa I. Silva-Lopez、Adam O. Barden、James A. Brozik

  DOI：10.1016/j.bmcl.2012.11.082

  日期：2013.2

  Described is the synthesis of 5-hydroxytryptamine-tetramethylrhodamine (5HT*); an indole nitrogen linked fluorescent conjugate of serotonin. Through a series fluorescence quenching experiments and experiments in the presence of a known competitive antagonist (Granisetron), it was shown that 5HT* specifically binds to purified homo-pentameric type-3 human serotonin receptors (5HT(3A)). The measured dissociation constant and Hill coefficient are K-d = 83 +/- 3 nM and n = 3.1 +/- 0.3, respectively which is indicative of multi-ligand binding and cooperativity similar to that of unconjugated serotonin. (c) 2012 Elsevier Ltd. All rights reserved.