5-甲基-3-(吡咯烷-2-基)异噁唑 | 1000932-34-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-甲基-3-(吡咯烷-2-基)异噁唑
• 中文别名: 5-甲基-3-(2-吡咯烷基)异恶唑
• 英文名称: 5-methyl-3-(pyrrolidin-2-yl)isoxazole
• 英文别名: 5-Methyl-3-pyrrolidin-2-ylisoxazole；5-methyl-3-pyrrolidin-2-yl-1,2-oxazole
• CAS: 1000932-34-2
• 化学式: C₈H₁₂N₂O
• mdl: MFCD09863362
• 分子量: 152.196
• InChiKey: QHCHHBRSMFGRQX-UHFFFAOYSA-N

物化性质

• 沸点：
  270.7±28.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-甲基-3-(吡咯烷-2-基)异噁唑 、 1-(isocyanatomethyl)adamantane 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以93%的产率得到N-(adamant-1-ylmethyl)-2-(5-methylisoxazol-3-yl)pyrrolidine-1-carboxamide
  参考文献：
  名称：

  1,3-Disubstituted and 1,3,3-trisubstituted adamantyl-ureas with isoxazole as soluble epoxide hydrolase inhibitors

  摘要：

  Adamantyl ureas are good soluble epoxide hydrolase (sEH) inhibitors; however they have limited solubility and rapid metabolism, thus limiting their usefulness in some therapeutic indications. Herein, we test the hypothesis that nodal substitution on the adamantane will help solubilize and stabilize the compounds. A series of compounds containing adamantane derivatives and isoxazole functional groups were developed. Overall, the presence of methyl on the nodal positions of adamantane yields higher water solubility than previously reported urea-based sEH inhibitors while maintaining high inhibition potency. However, it did not improve microsomal stability. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.066

文献信息

• [EN] 6-HETEROCYCLYL-4-MORPHOLIN-4-YLPYRIDINE-2-ONE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER AND DIABETES<br/>[FR] COMPOSÉS 6-HÉTÉROCYCLYL-4-MORPHOLIN-4-YLPYRIDINE-2-ONE UTILISÉS POUR LE TRAITEMENT DU CANCER ET DU DIABÈTE
  申请人：SPRINT BIOSCIENCE AB

  公开号：WO2017140843A1

  公开（公告）日：2017-08-24

  The invention provides novel 6-heterocyclyl-4-morpholin-4-yl-pyridine-2-one compounds of formula (I), pharmaceutical compositions containing such compounds, and methods for using such compounds in treatment of diseases including cancer, diabetes, inflammatory disease, neurodegenerative disorders, cardiovascular disorders and viral infections; wherein R1, R2, R3 and A are as defined in the specification.

  该发明提供了公式（I）的新型6-杂环基-4-吗啡啉-4-基吡啶-2-酮化合物，包含该化合物的药物组合物，以及使用该化合物治疗癌症、糖尿病、炎症性疾病、神经退行性疾病、心血管疾病和病毒感染等疾病的方法；其中R1、R2、R3和A如规范中所定义。
• 6-heterocyclyl-4-morpholin-4-ylpyridine-2-one compounds useful for the treatment of cancer and diabetes
  申请人：Sprint Bioscience AB

  公开号：US11179399B2

  公开（公告）日：2021-11-23

  The invention provides novel 6-heterocyclyl-4-morpholin-4-yl-pyridine-2-one compounds of formula (I), pharmaceutical compositions containing such compounds, and methods for using such compounds in treatment of diseases including cancer, diabetes, inflammatory disease, neurodegenerative disorders, cardiovascular disorders and viral infections; wherein R1, R2, R3 and A are as defined in the specification.

  本发明提供了新颖的式(I)的6-杂环基-4-吗啉-4-基吡啶-2-酮化合物、含有此类化合物的药物组合物以及使用此类化合物治疗包括癌症、糖尿病、炎症性疾病、神经退行性疾病、心血管疾病和病毒感染等疾病的方法；其中R1、R2、R3和A如说明书中所定义。
• Synthesis and Study of 1,3- and 1,3,3-Substituted Ureas Containing Isoxazole and Adamantane Fragments
  作者：G. M. Butov、V. V. Burmistrov、I. L. Dalinger、I. A. Vatsadze、T. K. Shkineva、D. V. Danilov

  DOI：10.1007/s10593-015-1643-3

  日期：2015.3

  A series of 1,3-disubstituted and 1,3,3-trisubstituted isoxazolyl- and adamantyl-functionalized ureas was synthesized. The resulting compounds are potent inhibitors of soluble epoxide hydrolase. The compounds were obtained in high yields under mild conditions. Water solubility of the synthesized ureas was found to exceed significantly that of known analogs.
• 6-HETEROCYCLYL-4-MORPHOLIN-4-YLPYRIDINE-2-ONE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER AND DIABETES
  申请人：Sprint Bioscience AB

  公开号：EP3416957A1

  公开（公告）日：2018-12-26
• 6-HETEROCYCLYL-4-MORPHOLIN-4-YLPYRIDIN-2-ONE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER AND DIABETES
  申请人：Sprint Bioscience AB

  公开号：EP3416957B1

  公开（公告）日：2020-07-01