3-{3-[5-(4-methoxybenzyloxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl}propanoic acid | 917910-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-{3-[5-(4-methoxybenzyloxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl}propanoic acid
• 英文别名: 3-{[5-(4-methoxybenzyloxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl}propionic acid；3-[3-[5-[(4-Methoxyphenyl)methoxy]pyridin-2-yl]-1,2,4-oxadiazol-5-yl]propanoic acid
• CAS: 917910-78-2
• 化学式: C₁₈H₁₇N₃O₅
• 分子量: 355.35
• InChiKey: BVERPQHOPYVLKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-{3-[5-(4-methoxybenzyloxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl}propanoic acid 在 ammonium hydroxide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-羟基丁二酰亚胺 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  The discovery of high affinity agonists of GPR109a with reduced serum shift and improved ADME properties

  摘要：

  Amino-anthranilic acid derivatives have been identified as a new class of low serum shifted, high affinity full agonists of the human orphan G-protein-coupled receptor GPR109a with improved ADME properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.116
• 作为产物：
  描述：

  5-((4-甲氧基苄基)氧基)皮考啉腈 在 吡啶 、 盐酸羟胺 、 水 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 7.0h， 生成 3-{3-[5-(4-methoxybenzyloxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl}propanoic acid
  参考文献：
  名称：

  NITROGEN-CONTAINING AROMATIC HETEROCYCLYL COMPOUND

  摘要：

  公开号：

  EP2308838B1

文献信息

• Niacin receptor agonists, compositions containing such compounds and methods of treatment
  申请人：Raghavan Subharekha

  公开号：US20060293364A1

  公开（公告）日：2006-12-28

  The present invention encompasses compounds of Formula I: as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating atherosclerosis, dyslipidemias and the like. Pharmaceutical compositions and methods of use are also included.

  本发明涵盖了Formula I的化合物： 以及其药用可接受的盐和水合物，用于治疗动脉粥样硬化、血脂异常等疾病。药物组合物和使用方法也包括在内。
• Niacin Receptor Agonists, Compositions Containing Such Compounds and Methods of Treatment
  申请人：Beresis Richard T.

  公开号：US20100204278A1

  公开（公告）日：2010-08-12

  The present invention encompasses compounds of Formula (I) as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating atherosclerosis, dyslipidemias and the like. Pharmaceutical compositions and methods of use are also included.

  本发明涵盖了公式（I）的化合物，以及其药学上可接受的盐和水合物，可用于治疗动脉粥样硬化，血脂异常等。还包括制药组合物和使用方法。
• Discovery of a Biaryl Cyclohexene Carboxylic Acid (MK-6892): A Potent and Selective High Affinity Niacin Receptor Full Agonist with Reduced Flushing Profiles in Animals as a Preclinical Candidate
  作者：Hong C. Shen、Fa-Xiang Ding、Subharekha Raghavan、Qiaolin Deng、Silvi Luell、Michael J. Forrest、Ester Carballo-Jane、Larissa C. Wilsie、Mihajlo L. Krsmanovic、Andrew K. Taggart、Kenneth K. Wu、Tsuei-Ju Wu、Kang Cheng、Ning Ren、Tian-Quan Cai、Qing Chen、Junying Wang、Michael S. Wolff、Xinchun Tong、Tom G. Holt、M. Gerard Waters、Milton L. Hammond、James R. Tata、Steven L. Colletti

  DOI：10.1021/jm100022r

  日期：2010.3.25

  Biaryl cyclohexene carboxylic acids were discovered as full and potent niacin receptor (GPR109A) agonists. Compound le (MK-6892) displayed excellent receptor activity, good PK across species, remarkably clean off-target profiles, good ancillary pharmacology, and superior therapeutic window over niacin regarding the FFA reduction versus vasodilation in rats and dogs.
• WO2008/51403
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of novel pyrrole derivatives as potent agonists for the niacin receptor GPR109A
  作者：Yuriko Miyazawa、Takahiro Yamaguchi、Mitsuhiro Yamaguchi、Keiko Tago、Akihiro Tamura、Daisuke Sugiyama、Takahide Aburatani、Tomohiro Nishizawa、Nobuya Kurikawa、Keita Kono

  DOI：10.1016/j.bmcl.2020.127105

  日期：2020.5

  Novel pyrrole derivatives were discovered as potent agonists of the niacin receptor, GPR109A. During the derivatization, compound 16 was found to be effective both in vitro and in vivo. The compound 16 exhibited a significant reduction of the non-esterified fatty acid in human GPR109A transgenic rats, and the duration of its in vivo efficacy was much longer than niacin.