6-nitro-3-((1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy)pyridine | 280141-83-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-nitro-3-((1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy)pyridine
• 英文别名: 1,1-Dimethylethyl (2S)-2-[[(6-nitro-3-pyridinyl)oxy]methyl]-1-azetidinecarboxylate；tert-butyl (2S)-2-[(6-nitropyridin-3-yl)oxymethyl]azetidine-1-carboxylate
• CAS: 280141-83-5
• 化学式: C₁₄H₁₉N₃O₅
• 分子量: 309.322
• InChiKey: SOYNAKXUBYVBBZ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  97.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-nitro-3-((1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy)pyridine 在 氢氟酸 作用下， 生成 6-[18F]fluoro-3-((1-tert-butoxycarbonyl)-2(S)-azetidinylmethoxy)pyridine
  参考文献：
  名称：

  Koren; Horti; Mukhin, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S409-S410

  摘要：

  DOI：
• 作为产物：
  描述：

  6-硝基吡啶-3-醇 、 (S)-1-BOC-2-氮杂环丁烷甲醇 生成 6-nitro-3-((1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy)pyridine
  参考文献：
  名称：

  Koren; Horti; Mukhin, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S409-S410

  摘要：

  DOI：

文献信息

• Koren; Horti; Mukhin, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S409-S410
  作者：Koren、Horti、Mukhin、Gundisch、Dannals、London

  DOI：——

  日期：——
• Synthesis and initialin vitro characterization of 6-[18F]fluoro-3-(2(S)-azetidinylmethoxy)pyridine, a high-affinity radioligand for central nicotinic acetylcholine receptors
  作者：Andrei O. Koren、Andrew G. Horti、Alexey G. Mukhin、Daniela G�ndisch、Robert F. Dannals、Edythe D. London

  DOI：10.1002/(sici)1099-1344(200004)43:5<413::aid-jlcr326>3.0.co;2-1

  日期：2000.4

  6-[F-18]Fluora-3-(2(S)-azetidinylmethoxy)pyridine ([F-18](1) under bar), a novel analogue of the high-affinity nicotinic acetylcholine receptor ligand, A-85380, was prepared by a two-step procedure from an appropriate nitro precursor. In the first step, a Kryptofix 222-assisted F-18 nucleophilic heteroaromatic substitution in 6-nitro-3-((1-tert-butoxycarbonyl-2(S)-azetidinyl)methoxy)pyridine provided a radio-fluorinated Boc-protected intermediate. Subsequent acidic deprotection of the intermediate gave [F-18](1) under bar with an overall radiochemical yield of 8 to 12% (non-decay-corrected). The typical synthesis time was ca. 110 min. Specific radioactivity of the final product ranged from 1000 to 4500 mCi/mu mol, as calculated at the end-of-synthesis. III vitro studies demonstrated that the novel radioligand bound to a single population of sites in rat brain membranes, presumably, to the alpha 4 beta 2 subtype of nicotinic acetylcholine receptor. This binding was characterized by a K-d value of 28 pM, consistent with the K-i value of 25 pM, derived previously for unlabeled (1) under bar in competition assays with (+/-)-[H-3]epibatidine.