tert-Butyl methyl{1-[2-(3-pyridyloxy)ethyl]cyclopropyl}carbamate | 387845-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl methyl{1-[2-(3-pyridyloxy)ethyl]cyclopropyl}carbamate
• 英文别名: tert-Butyl methyl{1-[2-(pyridin-3-yloxy)ethyl]cyclopropyl}carbamate；tert-butyl N-methyl-N-[1-(2-pyridin-3-yloxyethyl)cyclopropyl]carbamate
• CAS: 387845-64-9
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: WQFQHVWVMNIDMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-Butyl methyl{1-[2-(3-pyridyloxy)ethyl]cyclopropyl}carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到Methyl-{1-[2-(pyridin-3-yloxy)-ethyl]-cyclopropyl}-amine fumarate
  参考文献：
  名称：

  Preparation and affinity profile of novel nicotinic ligands

  摘要：

  Novel nicotinic ligands, characterized by the presence of an amino substituted cyclopropane ring connected to a pyridine nucleus, are described. Pharmacological investigation revealed that these compounds exhibit highest affinity for the rat alpha 4 beta 2 subtype of the nicotinic receptor with no affinity for the muscarinic receptor. No appreciable affinity for the muscular or for the ganglionic nicotinic receptor was observed at concentrations up to 10 mu M. The increase in cortical ACh release as well as a positive effect on memory in a social recognition test in rat are exemplified. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.075
• 作为产物：
  描述：

  3-羟基吡啶 、 tert-butyl N-[1-(2-hydroxyethyl)cyclopropyl]-N-methylcarbamate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到tert-Butyl methyl{1-[2-(3-pyridyloxy)ethyl]cyclopropyl}carbamate
  参考文献：
  名称：

  Preparation and affinity profile of novel nicotinic ligands

  摘要：

  Novel nicotinic ligands, characterized by the presence of an amino substituted cyclopropane ring connected to a pyridine nucleus, are described. Pharmacological investigation revealed that these compounds exhibit highest affinity for the rat alpha 4 beta 2 subtype of the nicotinic receptor with no affinity for the muscarinic receptor. No appreciable affinity for the muscular or for the ganglionic nicotinic receptor was observed at concentrations up to 10 mu M. The increase in cortical ACh release as well as a positive effect on memory in a social recognition test in rat are exemplified. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.075

文献信息

• 1,1- and 1,2-disubstituted cyclopropane compounds
  申请人：——

  公开号：US20020022643A1

  公开（公告）日：2002-02-21

  A compound selected from those of formula (I): 1 wherein: p represents an integer of from 0 to 6 inclusive, n represents an integer of from 0 to 6 inclusive, R 1 , and R 2 represent a group selected from hydrogen, alkyl, aryl and arylalkyl, or R 1 +R 2 form together with nitrogen carrying them saturated, monocyclic, or bicyclic system, X represents a group selected from oxygen, sulphur, a group —CH═CH—, methylene, a group of formula —HC═N—O— and a group of formula —O—CH 2 —CH═CH—, in which groups oxygen is linked to Y of the compounds of formula (I), Y represents a group selected from aryl, heteroaryl, arylalkyl, heteroarylalkyl, —C(O)—A, and —C(S)—A, A represents a group selected from alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, and NR 3 R 4 wherein R 3 , and R 4 represent a group selected from hydrogen, alkyl, aryl, and arylalkyl, or R 3 +R 4 form together with nitrogen carrying them monocyclic, or bicyclic (C 3 -C 10 ) system, its isomers and addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same are useful as specific nicotinic ligand of (&agr; 4 &bgr; 2 receptors.

  从式(I)中选择的化合物：其中：p表示0至6的整数，n表示0至6的整数，R1和R2表示从氢，烷基，芳基和芳基烷基中选择的基团，或R1+R2与携带它们的氮形成饱和的单环或双环系统，X表示从氧，硫，—CH2CH—，亚甲基，式为—HC=NO—和式为—O—CH2CH2CH=CH—的基团中选择的基团，在其中氧与式(I)中的Y连接，Y表示从芳基，杂芳基，芳基烷基，杂芳基烷基，—C（O）—A和—C（S）—A中选择的基团，A表示从烷基，芳基，杂芳基，芳基烷基，杂芳基烷基和NR3R4中选择的基团，其中R3和R4表示从氢，烷基，芳基和芳基烷基中选择的基团，或R3+R4与携带它们的氮形成单环或双环（C3-C10）系统，其异构体和与药学上可接受的酸或碱的加合物，以及含有它们的药物制剂，有用作为(&agr;4&bgr;2受体的特异性烟碱性配体。
• 1,1-and 1,2-disubstituted cyclopropane compounds
  申请人：Goldstein Solo

  公开号：US20050032845A1

  公开（公告）日：2005-02-10

  A compound selected from those of formula (1): wherein: p represents an integer of from 0 to 6 inclusive, n represents an integer of from 0 to 6 inclusive, R 1 , and R 2 represent a group selected from hydrogen, alkyl, aryl and arylalkyl, or R 1 +R 2 form together with nitrogen carrying them saturated, monocyclic, or bicyclic system, X represents a group selected from oxygen, sulphur, a group —CH═CH—, methylene, a group of formula —HC═N—O— and a group of formula —O—CH 2 —CH═CH—, in which groups oxygen is linked to Y of the compounds of formula (I), Y represents a group selected from aryl, heteroaryl, arylalkyl, heteroarylalkyl, —C(O)-A, and —C(S)-A, A represents a group selected from alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, and NR 3 R 4 wherein R 3 , and R 4 represent a group selected from hydrogen, alkyl, aryl, and arylalkyl, or R 3 +R 4 form together with nitrogen carrying them monocyclic, or bicyclic (C 3 -C 10 ) system, its isomers and addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same are useful as specific nicotinic ligand of α 4 β 2 receptors.

  从式（1）中选择的化合物：其中：p表示0至6的整数，n表示0至6的整数，R1和R2表示从氢，烷基，芳基和芳基烷基中选择的基团，或R1 + R2形成饱和的氮，单环或双环系统，X表示从氧，硫，-CH═CH-，亚甲基，式- HC═N-O-和式-O-CH2-CH═CH-中选择的基团，在这些基团中氧与式（I）中化合物的Y连接，Y表示从芳基，杂环芳基，芳基烷基，杂环芳基烷基，-C（O）-A和-C（S）-A中选择的基团，A表示从烷基，芳基，杂环芳基，芳基烷基，杂环芳基烷基和NR3R4中选择的基团，其中R3和R4表示从氢，烷基，芳基和芳基烷基中选择的基团，或R3 + R4形成单环或双环（C3-C10）系统，其异构体和与药物可接受的酸或碱的加合物，以及含有它们的药物制剂，作为α4β2受体的特异性烟碱性配体是有用的。
• Nouveaux composés cyclopropaniques 1,1 et 1,2-disubstitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1170281A1

  公开（公告）日：2002-01-09

  Composés de formule (I) : dans laquelle : preprésente un entier compris entre 0 et 6 inclus, nreprésente un entier compris entre 0 et 6 inclus, R1 et R2représentent un groupement choisi parmi atome d'hydrogène, groupement alkyle, aryle, et arylalkyle, ou R1+R2 forment ensemble, avec l'atome d'azote qui les porte, un système monocyclique ou bicyclique, saturé, Xreprésente un groupement choisi parmi atome d'oxygène, atome de soufre, groupement -CH=CH-, méthylène, groupement de formule -HC=N-O- et groupement de formule -O-CH2-CH=CH- dans lesquels l'atome d'oxygène est relié à la partie Y des composés de formule (I), Yreprésente un groupement choisi parmi aryle, hétéroaryle, arylalkyle, hétéroarylalkyle, -C(O)-A, et -C(S)-A, Areprésente un groupement choisi parmi alkyle, aryle, hétéroaryle, arylalkyle, hétéroarylalkyle, et NR3R4 dans lequel R3 et R4 représentent un groupement choisi parmi atome d'hydrogène, groupement alkyle, aryle, et arylalkyle, ou R3+R4 forment ensemble, avec l'atome d'azote qui les porte, un système monocyclique ou bicyclique en (C3-C10), leurs isomères ainsi que leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable. Médicaments.

  式(I)化合物 其中： 0-6（含）之间的整数、 n 代表介于 0 和 6 之间的整数、 R1 和 R2 代表选自氢原子、烷基、芳基和芳烷基的基团，或 R1+R2 与携带它们的氮原子一起形成饱和单环或双环体系、 X代表选自氧原子、硫原子、-CH=CH-基团、亚甲基、式-HC=N-O-基团和式-O-CH2-CH=CH-基团的基团，其中氧原子与式(I)化合物的 Y 部分相连、 Y 代表选自芳基、杂芳基、芳烷基、杂芳烷基、-C(O)-A 和 -C(S)-A 的基团、 代表选自烷基、芳基、杂芳基、芳烷基和杂芳烷基的基团，以及 NR3R4，其中 R3 和 R4 代表选自氢、烷基、芳基和芳烷基的基团，或 R3+R4 与携带它们的氮原子一起形成 (C3-C10) 单环或双环系统、 它们的异构体及其与药学上可接受的酸或碱的加成盐。 药用产品。
• Preparation and affinity profile of novel nicotinic ligands
  作者：Yves Charton、Claude Guillonneau、Brian Lockhart、Pierre Lestage、Solo Goldstein

  DOI：10.1016/j.bmcl.2007.12.075

  日期：2008.3

  Novel nicotinic ligands, characterized by the presence of an amino substituted cyclopropane ring connected to a pyridine nucleus, are described. Pharmacological investigation revealed that these compounds exhibit highest affinity for the rat alpha 4 beta 2 subtype of the nicotinic receptor with no affinity for the muscarinic receptor. No appreciable affinity for the muscular or for the ganglionic nicotinic receptor was observed at concentrations up to 10 mu M. The increase in cortical ACh release as well as a positive effect on memory in a social recognition test in rat are exemplified. (C) 2008 Elsevier Ltd. All rights reserved.