3-(2-吡啶)-5-(2-氯苯基)-1,2,4-噁二唑 | 27199-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(2-吡啶)-5-(2-氯苯基)-1,2,4-噁二唑
• 英文名称: 5-(2-chlorophenyl)-3-(pyridin-2-yl)-1,2,4-oxadiazole
• 英文别名: 2-(5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl)pyridine；2-[5-(2-chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridine；3-(pyridin-2-yl)-5-(2-chlorophenyl)-1,2,4-oxadiazole；3-(2-pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole；3-(2-Pyridyl)-5-(2-Chlorphenyl)-1,2,4-Oxadiazol；Pyridine, 2-[5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl]-；5-(2-chlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole
• CAS: 27199-42-4
• 化学式: C₁₃H₈ClN₃O
• 分子量: 257.679
• InChiKey: NGKWCJCCZGCLID-UHFFFAOYSA-N

物化性质

• 沸点：
  437.0±51.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基吡啶 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-(2-吡啶)-5-(2-氯苯基)-1,2,4-噁二唑
  参考文献：
  名称：

  Discovery and characterization of AZD9272 and AZD6538—Two novel mGluR5 negative allosteric modulators selected for clinical development

  摘要：

  AZD9272 and AZD6538 are two novel mGluR5 negative allosteric modulators selected for further clinical development. An initial high-throughput screening revealed leads with promising profiles, which were further optimized by minor, yet indispensable, structural modifications to bring forth these drug candidates. Advantageously, both compounds may be synthesized in as little as one step. Both are highly potent and selective for the human as well as the rat mGluR5 where they interact at the same binding site than MPEP. They are orally available, allow for long interval administration due to a high metabolic stability and long half-lives in rats and permeate the blood brain barrier to a high extent. AZD9272 has progressed into phase I clinical studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.100

文献信息

• Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
  申请人：——

  公开号：US20030055085A1

  公开（公告）日：2003-03-20

  The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.

  本发明提供了作为代谢型谷氨酸受体拮抗剂的化合物和药物组合物，用于治疗神经系统疾病和障碍。还公开了制备这些化合物的方法。
• A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O -acylamidoximes in the superbase system MOH/DMSO
  作者：Sergey Baykov、Tatyana Sharonova、Angelina Osipyan、Sergey Rozhkov、Anton Shetnev、Alexey Smirnov

  DOI：10.1016/j.tetlet.2016.05.071

  日期：2016.6

  Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within short reaction times (10–20 min). In addition, mild reaction conditions and a simple work-up procedure allow the synthesis of a wide range of heat-labile

  在本文中，我们报道了在超碱系统MOH / DMSO（M = Li，Na，K）中通过O-酰基酰胺基肟的环脱水作用，一种一般，便捷，有效的合成3,5-二取代-1,2,4-恶二唑的方法。在较短的反应时间内（10-20分钟）即可获得出色的分离产率（高达98％）。此外，温和的反应条件和简单的后处理程序可以合成多种热不稳定的含1,2,4-恶二唑的物质。
• A Simple and Straightforward Protocol to 3,5-Disubstituted 1,2,4-Oxadiazoles from Carboxylic Acids
  作者：Tadikonda Ramu、Sarakula Prasanthi、Nakka Mangarao、Gajula Mahaboob Basha、Rayavarapu Srinuvasarao、Vidavalur Siddaiah

  DOI：10.1246/cl.130187

  日期：2013.7.5

  A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acids and amidoximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmor...

  描述了一种方便的 1,2,4-恶二唑的一锅法合成。在2-氯-4,6-二甲氧基-1,3,5-三嗪(CDMT)和N-甲基莫尔...
• HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：NPS PHARMACEUTICALS, INC.

  公开号：EP1210344A1

  公开（公告）日：2002-06-05
• NEW USE
  申请人：AstraZeneca AB

  公开号：EP1896011A1

  公开（公告）日：2008-03-12