4-(chloromethyl)-5-ethyl-2-phenyl-1,3-oxazole | 1311277-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(chloromethyl)-5-ethyl-2-phenyl-1,3-oxazole
• 英文别名: 4-chloromethyl-5-ethyl-2-phenyloxazole；4-(Chloromethyl)-5-ethyl-2-phenyloxazole
• CAS: 1311277-25-4
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: MGBMNOYJNHMCAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.9±34.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(chloromethyl)-5-ethyl-2-phenyl-1,3-oxazole 在 盐酸 、 硫酸 、 水 、 potassium carbonate 、 溶剂黄146 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 73.25h， 生成
  参考文献：
  名称：

  Biological evaluation of novel benzisoxazole derivatives as PPARδ agonists

  摘要：

  We discovered novel peroxisome proliferator-activated receptor delta agonists with a characteristic benzisoxazole ring. Compound 5 exhibited potent human PPAR delta transactivation activity. Furthermore, it stimulated the differentiation of oligodendrocyte precursor cells in vitro. This indicates that this potential drug may be effective for the treatment of demyelinating disorders such as multiple sclerosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.053
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 盐酸 、 锂硼氢 、 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 乙酸–三乙胺 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 4-(chloromethyl)-5-ethyl-2-phenyl-1,3-oxazole
  参考文献：
  名称：

  新型两性离子化合物作为过氧化物酶体增殖物激活受体α/γ双激动剂的合成及其构效关系，具有改善的理化性质。

  摘要：

  我们在本文中描述了新型两性离子化合物作为基于非噻唑烷二酮（TZD）的过氧化物酶体增殖物激活受体（PPAR）α/γ双激动剂的设计，合成和构效关系（SAR）。在以前的报告中，我们获得了在db / db小鼠中显示出有效PPARα/γ双重激动活性以及极大的降糖作用的化合物1。但是，该化合物具有致命问题，例如有效的细胞色素P450（CYP）3A4直接抑制活性。因此，我们进行了药物优化以改善它们，同时保持有效的PPAR激动活性。结果，通过将呋喃环改变为低亲脂性的1,3,4-恶二唑环得以解决。另外，

  DOI：

  10.1248/cpb.c13-00513

文献信息

• OXADIAZOLONES AND DERIVATIVES THEREOF AS PEROXISOME PROLIFERATOR - ACTIVATED RECEPTOR (PPAR) DELTA AGONISTS
  申请人：KEIL Stefanie

  公开号：US20080255212A1

  公开（公告）日：2008-10-16

  The invention relates to oxadiazolones and to their physiologically acceptable salts and physiologically functional derivatives showing peroxisome proliferator activator receptor (PPAR) delta agonist activity comprising compounds of formula I, in which the R1-R7 substituents as well as the U, V, W, X Y and z radicals are as defined herein, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistance is involved; neurodegenerative diseases and/or de-myelinating disorders of the central and peripheral nervous systems and/or neurological diseases involving neuro-inflammatory processes and/or other peripheral neuropathies.

  本发明涉及氧化二氮杂环酮及其生理上可接受的盐和生理上功能衍生物，其显示过氧化物酶体增殖物激活受体（PPAR）δ激动剂活性，包括式I中的化合物，其中R1-R7取代基以及U、V、W、X、Y和z基团的定义如本文所述，以及它们的生理上可接受的盐和制备方法。这些化合物适用于治疗和/或预防脂肪酸代谢和葡萄糖利用障碍以及胰岛素抵抗涉及的疾病；中枢神经系统和/或周围神经系统的神经退行性疾病和/或去髓鞘疾病以及涉及神经炎症过程和/或其他周围神经病的神经疾病。
• METHODS FOR THE TREATMENT OF METABOLIC AND GLUCOSE UTILIZATION DISORDERS THROUGH THE ADMINISTRATION OF OXADIAZOLONES AND DERIVATIVES THEREOF AS PEROXISOME PROLIFERATOR - ACTIVATED RECEPTOR (PPAR) DELTA AGONISTS
  申请人：KEIL Stefanie

  公开号：US20080262052A1

  公开（公告）日：2008-10-23

  The invention relates to oxadiazolones and to their physiologically acceptable salts and physiologically functional derivatives showing PPARdelta agonist activity. What is described are compounds of the formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparations. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistance is involved; neurodegenerative diseases and/or de-myelinating disorders of the central and peripheral nervous systems and/or neurological diseases involving neuro-inflammatory processes and/or other peripheral neuropathies.

  本发明涉及氧化二唑酮及其生理上可接受的盐和生理上功能衍生物，显示PPARδ激动剂活性。所描述的化合物为公式I中的基团，其定义如上，并且它们的生理上可接受的盐和制备过程。该化合物适用于治疗和/或预防脂肪酸代谢紊乱和葡萄糖利用紊乱以及胰岛素抵抗涉及的疾病；中央和周围神经系统的神经退行性疾病和/或去髓鞘疾病和/或涉及神经炎症过程和/或其他周围神经病变的神经疾病。
• OXADIAZOLONES AND DERIVATIVES THEREOF AS PPAR DELTA AGONISTS
  申请人：KEIL Stefanie

  公开号：US20070179191A1

  公开（公告）日：2007-08-02

  The invention relates to oxadiazolones and to their physiologically acceptable salts and physiologically functional derivatives showing PPARdelta agonist activity. What is described are compounds of the formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparations. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistance is involved; neurodegenerative diseases and/or demyelinating disorders of the central and peripheral nervous systems and/or neurological diseases involving neuroinflammatory processes and/or other peripheral neuropathies.

  本发明涉及氧化二氮杂环酮及其生理上可接受的盐和生理功能衍生物，其具有PPARdelta激动剂活性。所描述的化合物为公式I中的基团所定义的化合物及其生理上可接受的盐和制备方法。这些化合物适用于治疗和/或预防脂肪酸代谢紊乱和葡萄糖利用紊乱以及胰岛素抵抗相关的疾病；中枢和周围神经系统的神经退行性疾病和/或脱髓鞘性疾病以及涉及神经炎性过程和/或其他周围神经病变的神经疾病。
• US7709509B2
  申请人：——

  公开号：US7709509B2

  公开（公告）日：2010-05-04
• Synthesis and Structure–Activity Relationships of Novel Zwitterionic Compounds as Peroxisome Proliferator Activated Receptor α/γ Dual Agonists with Improved Physicochemical Properties
  作者：Yoshihiro Shibata、Katsuji Kagechika、Mitsuhiro Yamaguchi、Kenji Yoshikawa、Kiyoshi Chiba、Hiromichi Takano、Chiyuki Akiyama、Mayumi Ono、Mina Nishi、Hideo Kubo、Yoshimasa Kobayashi、Hiroyuki Usui

  DOI：10.1248/cpb.c13-00513

  日期：——

  We describe herein the design, syntheses and structure-activity relationships (SAR) of novel zwitterionic compounds as non-thiazolidinedion (TZD) based peroxisome proliferator activated receptor (PPAR) α/γ dual agonists. In the previous report, we obtained compound 1 showing potent PPARα/γ dual agonistic activities, together with a great glucose lowering effect in the db/db mice. However, this compound

  我们在本文中描述了新型两性离子化合物作为基于非噻唑烷二酮（TZD）的过氧化物酶体增殖物激活受体（PPAR）α/γ双激动剂的设计，合成和构效关系（SAR）。在以前的报告中，我们获得了在db / db小鼠中显示出有效PPARα/γ双重激动活性以及极大的降糖作用的化合物1。但是，该化合物具有致命问题，例如有效的细胞色素P450（CYP）3A4直接抑制活性。因此，我们进行了药物优化以改善它们，同时保持有效的PPAR激动活性。结果，通过将呋喃环改变为低亲脂性的1,3,4-恶二唑环得以解决。另外，