(3-([(Tert-丁氧基羰基)氨基]甲基)吡啶-4-基)硼酸 | 433969-29-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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
• 中文名称: (3-([(Tert-丁氧基羰基)氨基]甲基)吡啶-4-基)硼酸
• 中文别名: 3-(叔丁氧羰氨基甲基)-吡啶-4-硼酸
• 英文名称: 3-(tert-butoxycarbonylaminomethyl)pyridyl-4-boronic acid
• 英文别名: 3-(boc-aminomethyl)pyridine-4-boronic acid；(3-(((tert-Butoxycarbonyl)amino)methyl)pyridin-4-yl)boronic acid；[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridin-4-yl]boronic acid
• CAS: 433969-29-0
• 化学式: C₁₁H₁₇BN₂O₄
• mdl: MFCD05664023
• 分子量: 252.078
• InChiKey: HKBZYJMXFLKZIR-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  91.7
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (3-([(Tert-丁氧基羰基)氨基]甲基)吡啶-4-基)硼酸 在 4-二甲氨基吡啶 、 lithium hydroxide 、 四(三苯基膦)钯 、 sodium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 {4-[2-(3-Methyl-butylcarbamoyl)-phenyl]-pyridin-3-ylmethyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Identification, Synthesis, and Activity of Novel Blockers of the Voltage-Gated Potassium Channel Kv1.5

  摘要：

  The voltage-gated potassium channel Kv1.5 is regarded as a promising target for the development of new atrial selective drugs with fewer side effects. In the present study the discovery of ortho,ortho-disubstituted bisaryl compounds as blockers of the Kv1.5 channel is presented. Several compounds of this new class were synthesized and screened for their ability to block Kv1.5 channels expressed in Xenopus oocytes. The observed structure-activity relationship (SAR) is described by a pharmacophore model that consists of three hydrophobic centers in a triangular arrangement. The hydrophobic centers are matched by a phenyl or pyridyl ring of the bisaryl core and both ends of the side chains. The most potent compounds (e.g., 17c and 17o) inhibited the Kv1.5 channel with sub-micromolar half-blocking concentrations and displayed 3-fold selectivity over Kv1.3 and no significant effect on the HERG channel and sodium currents. In addition, compounds 17c and 17m have already shown antiarrhythmic effects in a pig model.

  DOI：

  10.1021/jm0210461
• 作为产物：
  描述：

  N-BOC-3-氨甲基吡啶 在 叔丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以65%的产率得到(3-([(Tert-丁氧基羰基)氨基]甲基)吡啶-4-基)硼酸
  参考文献：
  名称：

  Identification, Synthesis, and Activity of Novel Blockers of the Voltage-Gated Potassium Channel Kv1.5

  摘要：

  The voltage-gated potassium channel Kv1.5 is regarded as a promising target for the development of new atrial selective drugs with fewer side effects. In the present study the discovery of ortho,ortho-disubstituted bisaryl compounds as blockers of the Kv1.5 channel is presented. Several compounds of this new class were synthesized and screened for their ability to block Kv1.5 channels expressed in Xenopus oocytes. The observed structure-activity relationship (SAR) is described by a pharmacophore model that consists of three hydrophobic centers in a triangular arrangement. The hydrophobic centers are matched by a phenyl or pyridyl ring of the bisaryl core and both ends of the side chains. The most potent compounds (e.g., 17c and 17o) inhibited the Kv1.5 channel with sub-micromolar half-blocking concentrations and displayed 3-fold selectivity over Kv1.3 and no significant effect on the HERG channel and sodium currents. In addition, compounds 17c and 17m have already shown antiarrhythmic effects in a pig model.

  DOI：

  10.1021/jm0210461

文献信息

• Ortho, ortho-substituted nitrogen-containing bisaryl compounds, processes for their preparation, their use as medicaments, and pharmaceutical preparation comprising them
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06794377B2

  公开（公告）日：2004-09-21

  Ortho, ortho-substituted nitrogen-containing bisaryl compounds, processes for their preparation, their use as medicaments, and pharmaceutical preparations including their use as antiarrhythmic active compounds, for example, for the treatment and prophylaxis of atrial arrhythmias, e.g. atrial fibrillation (AF) or atrial flutters. Compounds of the invention include compounds of the formula I

  本发明涉及Ortho，ortho-取代的含氮双芳基化合物、其制备方法、其作为药物的用途以及包括其作为抗心律失常活性化合物的制药制剂，例如，用于治疗和预防心房心律失常，例如心房颤动（AF）或心房扑动。本发明的化合物包括式I的化合物。
• WO2008/144222
  申请人：——

  公开号：——

  公开（公告）日：——
• Identification, Synthesis, and Activity of Novel Blockers of the Voltage-Gated Potassium Channel Kv1.5
  作者：Stefan Peukert、Joachim Brendel、Bernard Pirard、Andrea Brüggemann、Peter Below、Heinz-Werner Kleemann、Horst Hemmerle、Wolfgang Schmidt

  DOI：10.1021/jm0210461

  日期：2003.2.1

  The voltage-gated potassium channel Kv1.5 is regarded as a promising target for the development of new atrial selective drugs with fewer side effects. In the present study the discovery of ortho,ortho-disubstituted bisaryl compounds as blockers of the Kv1.5 channel is presented. Several compounds of this new class were synthesized and screened for their ability to block Kv1.5 channels expressed in Xenopus oocytes. The observed structure-activity relationship (SAR) is described by a pharmacophore model that consists of three hydrophobic centers in a triangular arrangement. The hydrophobic centers are matched by a phenyl or pyridyl ring of the bisaryl core and both ends of the side chains. The most potent compounds (e.g., 17c and 17o) inhibited the Kv1.5 channel with sub-micromolar half-blocking concentrations and displayed 3-fold selectivity over Kv1.3 and no significant effect on the HERG channel and sodium currents. In addition, compounds 17c and 17m have already shown antiarrhythmic effects in a pig model.