3-苄氧基-5-羟基吡啶 | 209328-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-苄氧基-5-羟基吡啶
• 英文名称: 3-benzyloxy-5-hydroxypyridine
• 英文别名: 5-(benzyloxy)pyridin-3-ol；5-(Phenyl methoxy)pyridin-3-ol；5-phenylmethoxypyridin-3-ol
• CAS: 209328-93-8
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: YWNDNQACHFFODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-苄氧基-5-羟基吡啶 在 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (R)-1-((5-(benzyloxy)pyridin-3-yl)oxy)-3-((2-hydroxyethyl)amino)propan-2-ol
  参考文献：
  名称：

  NOVEL P62 LIGAND COMPOUND, AND COMPOSITION CONTAINING SAME FOR PREVENTING, AMELIORATING, OR TREATING PROTEINOPATHIES

  摘要：

  Novel p62 ligand compounds, or a stereoisomer, a solvate, a hydrate, or a prodrug thereof are disclosed. The novel compounds, stereoisomer, solvate, hydrate, or prodrug activates selective autophagy in cells to selectively remove proteins, organelles, and coagulations in the body, and thus can be advantageously used as a pharmaceutical composition for preventing, ameliorating, or treating various proteinopathies. Compositions such as pharmaceutical composition or food compositions containing the novel p62 ligand compounds, stereoisomer, solvate, hydrate, or prodrug thereof as well as uses thereof are disclosed.

  公开号：

  US20220402873A1
• 作为产物：
  描述：

  3-苯甲氧基-5-溴吡啶 在 sodium hydroxide 、 tetrafluoroboric acid 、 氨 、 copper(I) bromide 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 生成 3-苄氧基-5-羟基吡啶
  参考文献：
  名称：

  与ABT-594（一种有效的非阿片类镇痛药）相关的结构活性研究：吡啶和氮杂环丁烷环取代对小鼠烟碱型乙酰胆碱受体结合亲和力和镇痛活性的影响。

  摘要：

  制备了类似物A-98593（1）及其对映体ABT-594（2），在吡啶环上具有多个取代基，并测试了与大鼠脑中烟碱乙酰胆碱受体结合位点的亲和力以及在小鼠热板测定中的镇痛活性。多种修饰类型与对[3H]胱氨酸结合位点的高亲和力相一致。相比之下，仅选择的修饰导致止痛效果保持在与1和2相同的范围内。还制备了在氮杂环丁烷环的3位带有一个或两个甲基取代基的2的类似物，发现它们的活性实质上较低。两种测定。

  DOI：

  10.1016/s0960-894x(98)00504-6

文献信息

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

  公开号：US06437138B1

  公开（公告）日：2002-08-20

  Novel 3-pyridyloxymethyl heterocyclic ether compounds of the formula: or the pharmaceutically-acceptable salts or prodrugs thereof are selective and potent ligands at neuronal nicotinic cholinergic channel receptors, and are effective in controlling synaptic transmission. Key intermediates and processes using this key intermediates to produce compounds of formula I with the variables defined in the specification are also described.

  新型3-吡啶氧甲基杂环醚化合物的化学式为： 或其药学上可接受的盐或前药是神经元胆碱能受体选择性和有效的配体，并且在控制突触传递方面具有良好效果。还描述了使用这些关键中间体的关键中间体和过程，以生产具有规范中定义的变量的化合物I的方法。
• 3-Pyridyl enantiomers and their use as analgesics
  申请人：Abbott Laboratories

  公开号：US06133253A1

  公开（公告）日：2000-10-17

  The present invention relates to a method of controlling pain in mammals, including humans, comprising administering to a mammal or patient in need of treatment thereof selected compounds of formula I: ##STR1## or a pharmaceutically acceptable salt thereof. The invention further relates to selected (R) and (S) compounds of formula I above which are useful as analgesics as well as neuronal cell death preventors and anti-inflammatories.

  本发明涉及一种控制哺乳动物（包括人类）疼痛的方法，包括向需要治疗的哺乳动物或患者施用公式I所选化合物：##STR1##或其药学上可接受的盐。该发明还涉及上述公式I的选定(R)和(S)化合物，其可用作镇痛剂、神经细胞凋亡抑制剂和抗炎药。
• PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE
  申请人：——

  公开号：US20010014691A1

  公开（公告）日：2001-08-16

  Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines. Exemplary compounds include dimethyl(2-(3-pyridyloxy)ethylamine, dimethyl(4-(3-pyridyloxy)butyl)amine, 2-(3-pyridyloxy)ethylamine, 4-(3-pyridyloxy)butylamine, methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine, ethyl(3-(3-pyridyloxy)propyl)amine, methyl(2-(3-pyridyloxy)ethyl)amine, methyl(3-(6-methyl(3-pyridyloxy))propyl)amine, (3-(3-methoxyphenoxy)propyl)methylamine, (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)methylamine, dimethyl(3-(3-pyridyloxy)propyl)amine, 3-(3-pyridyloxy)propylamine, methyl(4-(3-pyridyloxy)butyl)amine, 3-(5-chloro-3-pyridyloxy)propyl amine, methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine, (3-(5-chloro(3-pyridyloxy))propyl) methylamine, methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine, methyl(3-(2-methyl(3-pyridyloxy))propyl)amine, (methylethyl)(3-(3-pyridyloxy)propyl)amine, benzyl(3-(3-pyridyloxy)propyl)amine, cyclopropyl(3-(3-pyridyloxy)-propyl)amine, methyl(1-methyl-3-(3-pyridyloxy)propyl)amine, methyl(3-(3-nitrophenoxy)propyl)amine, 1-(3-chloropropoxy)-3-nitrobenzene, (3-(3-aminophenoxy)propyl)methylamine,dimethyl (3-(3-(methylamino)-propoxy)phenyl)amine, methyl(3-tricyclo[7.3.1.0<5,13>]tridec-2-yloxypropyl)amine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, 3-(4-piperidinyloxy)pyridine and 3-((3S)-3-pyrrolidinyloxy)pyridine.

  患有或易受中枢神经系统疾病等病症和紊乱的患者，通过向需要的患者施用芳基氧烷胺类化合物进行治疗，包括吡啶氧烷胺和苯氧烷胺。示例化合物包括二甲基(2-(3-吡啶氧基)乙基)胺，二甲基(4-(3-吡啶氧基)丁基)胺，2-(3-吡啶氧基)乙基胺，4-(3-吡啶氧基)丁基胺，甲基(3-(5-甲氧基-3-吡啶氧基)丙基)胺，乙基(3-(3-吡啶氧基)丙基)胺，甲基(2-(3-吡啶氧基)乙基)胺，甲基(3-(6-甲基(3-吡啶氧基))丙基)胺，(3-(3-甲氧基苯氧基)丙基)甲基胺，(3-(5-氯(3-吡啶氧基))-1-甲基丙基)甲基胺，二甲基(3-(3-吡啶氧基)丙基)胺，3-(3-吡啶氧基)丙基胺，甲基(4-(3-吡啶氧基)丁基)胺，3-(5-氯-3-吡啶氧基)丙基胺，甲基(3-(5-异丙氧基-3-吡啶氧基)丙基)胺，(3-(5-氯(3-吡啶氧基))丙基)甲基胺，甲基(3-(5-(苯甲氧基)(3-吡啶氧基))丙基)胺，甲基(3-(2-甲基(3-吡啶氧基))丙基)胺，(甲基乙基)(3-(3-吡啶氧基)丙基)胺，苄基(3-(3-吡啶氧基)丙基)胺，环丙基(3-(3-吡啶氧基)-丙基)胺，甲基(1-甲基-3-(3-吡啶氧基)丙基)胺，甲基(3-(3-硝基苯氧基)丙基)胺，1-(3-氯丙氧基)-3-硝基苯，(3-(3-氨基苯氧基)丙基)甲基胺，二甲基(3-(3-(甲氨基)-丙氧基)苯基)胺，甲基(3-三环七叁.壹.零<5,13>三十二氧基丙基)胺，(3-苯并三.四-壹,三-二氧杂环戊氧基丙基)甲基胺，3-(4-哌啶氧基)吡啶和3-((3S)-3-吡咯啶氧基)吡啶。
• Pharmaceutical compositions and methods for use
  申请人：Targacept, Inc.

  公开号：US06441006B2

  公开（公告）日：2002-08-27

  Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines. Exemplary compounds include dimethyl(2-(3-pyridyloxy)ethylamine, dimethyl(4-(3-pyridyloxy)butyl)amine, 2-(3-pyridyloxy)ethylamine, 4-(3-pyridyloxy)butylamine, methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine, ethyl(3-(3-pyridyloxy)propyl)amine, methyl(2-(3-pyridyloxy)ethyl)amine, methyl(3-(6-methyl(3-pyridyloxy))propyl)amine, (3-(3-methoxyphenoxy)propyl)methylamine, (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)methylamine, dimethyl(3-(3-pyridyloxy)propyl)amine, 3-(3-pyridyloxy)propylamine, methyl(4-(3-pyridyloxy)butyl)amine, 3-(5-chloro-3-pyridyloxy)propylamine, methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine, (3-(5-chloro(3-pyridyloxy))propyl)methylamine, methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine, methyl(3-(2-methyl(3-pyridyloxy))propyl)amine, (methylethyl)(3-(3-pyridyloxy)propyl)amine, benzyl(3-(3-pyridyloxy)propyl)amine, cyclopropyl(3-(3-pyridyloxy)-propyl)amine, methyl(1-methyl-3-(3-pyridyloxy)propyl)amine, methyl(3-(3-nitrophenoxy)propyl)amine, 1-(3-chloropropoxy)-3-nitrobenzene, (3-(3-aminophenoxy)propyl)methylamine, dimethyl(3-(3-(methylamino)-propoxy)phenyl)amine, methyl(3-tricyclo[7.3.1.0<5,13>]tridec-2-yloxypropyl)amine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, 3-(4-piperidinyloxy)pyridine and 3-((3S)-3-pyrrolidinyloxy)pyridine.

  对于容易受到或患有中枢神经系统疾病等疾病和疾病的患者，可以通过给予需要的患者芳基氧烷胺来进行治疗，包括吡啶氧烷胺和苯氧烷胺。示例化合物包括二甲基(2-(3-吡啶氧基)乙基)胺，二甲基(4-(3-吡啶氧基)丁基)胺，2-(3-吡啶氧基)乙基胺，4-(3-吡啶氧基)丁基胺，甲基(3-(5-甲氧基-3-吡啶氧基)丙基)胺，乙基(3-(3-吡啶氧基)丙基)胺，甲基(2-(3-吡啶氧基)乙基)胺，甲基(3-(6-甲基(3-吡啶氧基))丙基)胺，(3-(3-甲氧基苯氧基)丙基)甲基胺，(3-(5-氯(3-吡啶氧基))-1-甲基丙基)甲基胺，二甲基(3-(3-吡啶氧基)丙基)胺，3-(3-吡啶氧基)丙基胺，甲基(4-(3-吡啶氧基)丁基)胺，3-(5-氯-3-吡啶氧基)丙基胺，甲基(3-(5-异丙氧基-3-吡啶氧基)丙基)胺，(3-(5-氯(3-吡啶氧基))丙基)甲基胺，甲基(3-(5-(苯甲氧基)(3-吡啶氧基))丙基)胺，甲基(3-(2-甲基(3-吡啶氧基))丙基)胺，(甲基乙基)(3-(3-吡啶氧基)丙基)胺，苄基(3-(3-吡啶氧基)丙基)胺，环丙基(3-(3-吡啶氧基)-丙基)胺，甲基(1-甲基-3-(3-吡啶氧基)丙基)胺，甲基(3-(3-硝基苯氧基)丙基)胺，1-(3-氯丙氧基)-3-硝基苯，(3-(3-氨基苯氧基)丙基)甲基胺，二甲基(3-(3-(甲基氨基)-丙氧基)苯基)胺，甲基(3-三环[7.3.1.0<5,13>]十三烷-2-氧基丙基)胺，(3-苯并[3,4-d]1,3-二噁烷-5-氧基丙基)甲基胺，3-(4-哌啶氧基)吡啶和3-((3S)-3-吡咯烷氧基)吡啶。
• Chemistry and Pharmacology of a Series of Unichiral Analogues of 2-(2-Pyrrolidinyl)-1,4-benzodioxane, Prolinol Phenyl Ether, and Prolinol 3-Pyridyl Ether Designed as α4β2-Nicotinic Acetylcholine Receptor Agonists
  作者：Cristiano Bolchi、Ermanno Valoti、Cecilia Gotti、Francesca Fasoli、Paola Ruggeri、Laura Fumagalli、Matteo Binda、Vanessa Mucchietto、Miriam Sciaccaluga、Roberta Budriesi、Sergio Fucile、Marco Pallavicini

  DOI：10.1021/acs.jmedchem.5b00904

  日期：2015.8.27

  is changed. High α4β2 affinity and selectivity are also attained by meta hydroxylating the 3-pyridyl and the phenyl ethers of (S)-N-methylprolinol and the phenyl ether of (S)-2-azetidinemethanol, known α4β2 agonists, although the interaction mode of the aryloxymethylene substructure cannot be assimilated to that of benzodioxane. Indeed, the α4β2 and α3β4 functional tests well differentiate behaviors

  通过打开二恶烷来设计2 R，2 'S -2-（1'-甲基-2'-吡咯烷基）-7-羟基-1,4-苯并二恶烷的一些非手性类似物，这是一种有效的选择性α4β2-nAChR部分激动剂。并用氮气代替羟基碳。将所得的3-吡啶基和米羟苯基醚具有高亲和力α4β2和良好的亚型选择性，如果OH选自苯基除去或吡啶氮的位置被改变了迷路。高α4β2亲和力和选择性也通过间位羟基化的3-吡啶基和苯基醚（达到小号） - ñ -methylprolinol和的苯基醚（小号）-2-氮杂环丁烷甲醇，已知的α4β2激动剂，尽管芳氧亚甲基亚结构的相互作用方式不能与苯并二恶烷的相互作用方式同化。确实，α4β2和α3β4功能测试很好地区分了结合测试同源的行为：N-甲基脯氨醇的3-羟基苯基和5-羟基-3-吡啶基醚都是α4β2完全激动剂，但只有后者是高度α4β2/α3β4选择性，而有效和选择性的部分α4β2激动作用是羟基苯并二恶烷衍生物及其两个开放的半刚性类似物的特征。