4-[4-(2-甲氧基乙氧基)苯基]哌啶 | 377730-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-[4-(2-甲氧基乙氧基)苯基]哌啶
• 英文名称: 4-(4-(2-methoxyethoxy)phenyl)piperidine
• 英文别名: 4-[4-(2-Methoxyethoxy)phenyl]piperidine
• CAS: 377730-06-8
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: ZSYWGSJEQRTYHN-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±42.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 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：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-(2-甲氧基乙氧基)苯基]哌啶 、 8-氯-3-(环丙基甲基)-7-碘-[1,2,4]三唑并[4,3-A]吡啶 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 、 盐酸 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 以22%的产率得到8-chloro-3-(cyclopropylmethyl)-7-(4-(4-(2-methoxyethoxy)phenyl)piperidin-1-yl)[1,2,4]triazolo[4,3-a]pyridine hydrochloride
  参考文献：
  名称：

  推定的5-HT2A / mGlu2受体复合物的异二价配体的设计，合成和药理学表征。

  摘要：

  我们报告了针对5-HT 2A拮抗剂MDL-100,907和mGlu 2 ago-PAM JNJ-42491293的推定异聚5 -HT 2A / mGlu 2受体复合物的第一系列异二价配体的合成。使用Ca 2在表达5-HT 2A-，mGlu 2 / Gqo5-，5-HT 2A / mGlu 2-和5-HT 2A / mGlu 2 / Gqo5的HEK293细胞中表征一价和异二价配体的功能特性。+成像分析和[ 3H]酮色林结合测定。在5-HT 2A / mGlu 2和5-HT 2A / mGlu 2 / Gqo5细胞中的两个受体之间观察到明显的功能性串扰。虽然合成的一价配体保留了5-HT 2A拮抗剂和mGlu 2 ago-PAM的功能，但七个二价配体抑制了5-HT 2A / mGlu 2细胞中5-HT诱导的应答以及5-HT和Glu诱导的应答5-HT 2A / mGlu 2中的响应/ Gqo5细

  DOI：

  10.1021/acs.jmedchem.0c01058
• 作为产物：
  描述：

  1-溴-4-(2-甲氧基乙氧基)苯 在 palladium on activated charcoal 三乙基硅烷 、 正丁基锂 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、98.06 kPa 条件下， 生成 4-[4-(2-甲氧基乙氧基)苯基]哌啶
  参考文献：
  名称：

  3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A2A antagonists

  摘要：

  A novel series of 3-substituted-8-aryl-[1,2,4]-triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A(2A) receptor antagonists with improved selectivity over the A(1) receptor, physiochemical properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound 27 displayed both superior in vitro and highly promising in vivo profiles. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.104

文献信息

• 2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1
  作者：Julius J. Matasi、John P. Caldwell、Hongtao Zhang、Ahmad Fawzi、Mary E. Cohen-Williams、Geoffrey B. Varty、Deen B. Tulshian

  DOI：10.1016/j.bmcl.2005.05.086

  日期：2005.8

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.
• USRE44205E1
  申请人：——

  公开号：USRE44205E1

  公开（公告）日：2013-05-07
• Design, Synthesis, and Pharmacological Characterization of Heterobivalent Ligands for the Putative 5-HT_2A/mGlu₂ Receptor Complex
  作者：Christian B. M. Poulie、Na Liu、Anders A. Jensen、Lennart Bunch

  DOI：10.1021/acs.jmedchem.0c01058

  日期：2020.9.10

  We report the synthesis of the first series of heterobivalent ligands targeting the putative heteromeric 5-HT2A/mGlu2 receptor complex, based on the 5-HT2A antagonist MDL-100,907 and the mGlu2 ago-PAM JNJ-42491293. The functional properties of monovalent and heterobivalent ligands were characterized in 5-HT2A-, mGlu2/Gqo5-, 5-HT2A/mGlu2-, and 5-HT2A/mGlu2/Gqo5-expressing HEK293 cells using a Ca2+ imaging

  我们报告了针对5-HT 2A拮抗剂MDL-100,907和mGlu 2 ago-PAM JNJ-42491293的推定异聚5 -HT 2A / mGlu 2受体复合物的第一系列异二价配体的合成。使用Ca 2在表达5-HT 2A-，mGlu 2 / Gqo5-，5-HT 2A / mGlu 2-和5-HT 2A / mGlu 2 / Gqo5的HEK293细胞中表征一价和异二价配体的功能特性。+成像分析和[ 3H]酮色林结合测定。在5-HT 2A / mGlu 2和5-HT 2A / mGlu 2 / Gqo5细胞中的两个受体之间观察到明显的功能性串扰。虽然合成的一价配体保留了5-HT 2A拮抗剂和mGlu 2 ago-PAM的功能，但七个二价配体抑制了5-HT 2A / mGlu 2细胞中5-HT诱导的应答以及5-HT和Glu诱导的应答5-HT 2A / mGlu 2中的响应/ Gqo5细
• 3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A2A antagonists
  作者：Lisa S. Silverman、John P. Caldwell、William J. Greenlee、Eugenia Kiselgof、Julius J. Matasi、Deen B. Tulshian、Leyla Arik、Carolyn Foster、Rosalia Bertorelli、Angela Monopoli、Ennio Ongini

  DOI：10.1016/j.bmcl.2006.12.104

  日期：2007.3

  A novel series of 3-substituted-8-aryl-[1,2,4]-triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A(2A) receptor antagonists with improved selectivity over the A(1) receptor, physiochemical properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound 27 displayed both superior in vitro and highly promising in vivo profiles. (c) 2007 Elsevier Ltd. All rights reserved.