3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5-bromo-pyridine-N-oxide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5-bromo-pyridine-N-oxide
• 英文别名: 3-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine 1-oxide；3-bromo-5-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]-1-oxidopyridin-1-ium
• 化学式: C₁₁H₁₅BrN₂O₂
• 分子量: 287.156
• InChiKey: DNCDPNGUBXTJCS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5-bromo-pyridine-N-oxide 、 sodium methylate 在 水 、 silica gel 作用下， 以 甲醇 为溶剂， 生成 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5-methoxy-pyridine-N-oxide
  参考文献：
  名称：

  Heterocyclic ether compounds useful in controlling neurotransmitter

  摘要：

  该专利涉及一种新型杂环醚化合物，其化学式为：##STR1## 其中，*，A，B，n，R.sup.1，R.sup.2和X都有特定的定义，或其药学上可接受的盐或前药，可用于选择性激活或抑制神经递质的释放。同时，该专利还涉及这些化合物的治疗有效的药物组合物，以及使用上述组合物在哺乳动物中激活或抑制神经递质的释放。

  公开号：

  US05914328A1
• 作为产物：
  描述：

  N-甲基-L-脯氨醇 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 生成 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5-bromo-pyridine-N-oxide
  参考文献：
  名称：

  Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist

  摘要：

  Analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine (A-84543, 1) with 2-, 4-, 5-, and 6-substituents on the pyridine ring were synthesized. These analogs exhibited Ki values ranging from 0.15 to > 9,000 nM when tested in vitro for neuronal nicotinic acetylcholine receptor binding activity. Assessment of functional activity at subtypes of neuronal nicotinic acetylcholine receptors indicates that pyridine substitution can have a profound effect on efficacy at these subtypes, and several subtype-selective agonists and antagonists have been identified. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00019-5

文献信息

• 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling
  申请人：Abbott Laboratories

  公开号：US05948793A1

  公开（公告）日：1999-09-07

  Novel heterocyclic ether compounds of the formula: ##STR1## wherein n, *, R.sup.1, R.sup.2, R.sup.3 and y are specifically defined, or pharmaceutically acceptable salts or prodrugs thereof, which are useful in selectively controlling neurotransmitter release; therapeutically-effective pharmaceutical compositions of these compounds; and use of said compositions to selectively control neurotransmitter release in mammals.

  新型杂环醚化合物的化学式为：##STR1## 其中n，*，R.sup.1，R.sup.2，R.sup.3和y具体定义，或其药学上可接受的盐或前药，可用于选择性控制神经递质释放；这些化合物的治疗有效药物组合物；以及利用所述组合物在哺乳动物中选择性控制神经递质释放。
• US5914328A
  申请人：——

  公开号：US5914328A

  公开（公告）日：1999-06-22
• US5948793A
  申请人：——

  公开号：US5948793A

  公开（公告）日：1999-09-07
• Heterocyclic ether compounds useful in controlling neurotransmitter
  申请人：Abbott Laboratories

  公开号：US05914328A1

  公开（公告）日：1999-06-22

  Novel heterocyclic ether compounds of the formula: ##STR1## wherein *, A,B, n, R.sup.1, R.sup.2 and X are specifically defined, or pharmaceutically-acceptable salts or prodrugs thereof, which are useful in selectively activating or inhibiting neurotransmitter release; to therapeutically-effective pharmaceutical compositions of these compounds; and to the use of said compositions to activate or inhibit neurotransmitter release in mammals.

  新型杂环醚化合物的化学式为：##STR1## 其中，*、A、B、n、R.sup.1、R.sup.2 和 X 具体定义，或其在药学上可接受的盐或前药，可用于选择性激活或抑制神经递质释放；这些化合物的治疗有效药物组合物；以及使用所述组合物在哺乳动物中激活或抑制神经递质释放。
• Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist
  作者：Nan-Horng Lin、David E Gunn、Yihong Li、Yun He、Hao Bai、Keith B Ryther、Theresa Kuntzweiler、Diana L Donnelly-Roberts、David J Anderson、Jeffrey E Campbell、James P Sullivan、Stephen P Arneric、Mark W Holladay

  DOI：10.1016/s0960-894x(98)00019-5

  日期：1998.2

  Analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine (A-84543, 1) with 2-, 4-, 5-, and 6-substituents on the pyridine ring were synthesized. These analogs exhibited Ki values ranging from 0.15 to > 9,000 nM when tested in vitro for neuronal nicotinic acetylcholine receptor binding activity. Assessment of functional activity at subtypes of neuronal nicotinic acetylcholine receptors indicates that pyridine substitution can have a profound effect on efficacy at these subtypes, and several subtype-selective agonists and antagonists have been identified. (C) 1998 Elsevier Science Ltd. All rights reserved.