[(6-methoxy-pyridin-3-yl)-(toluene-2-sulfonyl)-amino]-acetic acid | 680591-44-0

• 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: [(6-methoxy-pyridin-3-yl)-(toluene-2-sulfonyl)-amino]-acetic acid
• 英文别名: N-(6-Methoxy-3-pyridinyl)-N-[(2-methylphenyl)sulfonyl]glycine；2-[(6-methoxypyridin-3-yl)-(2-methylphenyl)sulfonylamino]acetic acid
• CAS: 680591-44-0
• 化学式: C₁₅H₁₆N₂O₅S
• 分子量: 336.368
• InChiKey: MQCMHESYTKWLGP-UHFFFAOYSA-N

物化性质

• 沸点：
  557.4±60.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(6-methoxy-pyridin-3-yl)-(toluene-2-sulfonyl)-amino]-acetic acid 在 三甲基氯硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 N-ethyl-2-[(2-methylphenyl)sulfonyl-(6-oxo-1H-pyridin-3-yl)amino]-N-(pyridin-3-ylmethyl)acetamide
  参考文献：
  名称：

  Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors

  摘要：

  EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [H-3]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [C-11] N-ethyl-2-(N-(6-methoxypyridin- 3-yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl) acetamide ([C-11] EMPA), and evaluation as a potential PET tracer for OX2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [C-11] CH3I in the presence of cesium carbonate in DMSO at room temp afforded [C-11] EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [C-11] CH3I at EOS) with >= 95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [C-11] EMPA also showed poor uptake in both rats and baboon as measured with PET imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.079
• 作为产物：
  描述：

  邻甲苯磺酰氯 在 吡啶 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 [(6-methoxy-pyridin-3-yl)-(toluene-2-sulfonyl)-amino]-acetic acid
  参考文献：
  名称：

  Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors

  摘要：

  EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [H-3]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [C-11] N-ethyl-2-(N-(6-methoxypyridin- 3-yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl) acetamide ([C-11] EMPA), and evaluation as a potential PET tracer for OX2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [C-11] CH3I in the presence of cesium carbonate in DMSO at room temp afforded [C-11] EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [C-11] CH3I at EOS) with >= 95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [C-11] EMPA also showed poor uptake in both rats and baboon as measured with PET imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.079

文献信息

• Sulfonylamino-acetic acid derivatives
  申请人：Aissaoui Hamed

  公开号：US20060014783A1

  公开（公告）日：2006-01-19

  The invention relates to novel sulfonylamino-acetic acid derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of such compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.

  本发明涉及一种新型磺酰氨基乙酸衍生物及其作为制备药物组合物中的活性成分的用途。本发明还涉及相关方面，包括制备这些化合物的过程，含有其中一种或多种化合物的药物组合物，特别是它们作为促进睡眠的药物和促进睡眠的药物。
• SULFONYLAMINO-ACETIC ACID DERIVATIVES
  申请人：Aissaoui Hamed

  公开号：US20070244156A1

  公开（公告）日：2007-10-18

  The invention relates to novel sulfonylamino-acetic acid derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of such compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.

  本发明涉及新型磺酰氨基乙酸衍生物及其作为制备药物组成的活性成分的用途。本发明还涉及相关方面，包括制备这些化合物的过程、含有这些化合物中的一个或多个的药物组合物，特别是它们作为促进睡眠的药物的用途。
• SULFONYLAMINO-ACETIC ACID DERIVATIVES AND THEIR USE AS OREXIN RECEPTOR ANTAGONISTS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1554239A2

  公开（公告）日：2005-07-20
• US7279578B2
  申请人：——

  公开号：US7279578B2

  公开（公告）日：2007-10-09
• US7435815B2
  申请人：——

  公开号：US7435815B2

  公开（公告）日：2008-10-14