N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide | 1520080-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide
• 英文别名: S-Desmethyl S-Chloromethyl Dronedarone；N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1-benzofuran-5-yl]-1-chloromethanesulfonamide
• CAS: 1520080-11-8
• 化学式: C₃₁H₄₃ClN₂O₅S
• 分子量: 591.212
• InChiKey: QCNADTWLVZHBMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (5-氨基-2-丁基-3-苯并呋喃基)[4-[3-(二丁基氨基)丙氧基]苯基]甲酮 、 氯甲磺酰氯 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82.6%的产率得到N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide
  参考文献：
  名称：

  Identification and Characterization of Potential Impurities of Dronedarone Hydrochloride

  摘要：

  Six potential process related impurities were detected during the impurity profile study of an antiarrhythmic drug substance, Dronedarone (1). Simple high performance liquid chromatography and liquid chromatography-mass spectrometry methods were used for the detection of these process impurities. Based on the synthesis and spectral data (MS, IR, H-1 NMR, C-13 NMR, and DEPT), the structures of these impurities were characterized as 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran (impurity I); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide (impurity II); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide (impurity III); N-{2-propyl-3-[4-(3-dibutylaminopropoxy)benzoyl]benzofuran-5-yl}-methanesulfonamide (impurity IV); N-(2-butyl-3-(4-(3(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-formamide (impurity V); and (2-butyl-5-((3-(dibutylamino)propyl)amino)benzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone (impurity VI). The synthesis and characterization of these impurities are discussed in detail.

  DOI：

  10.1021/op400190b

文献信息

• Compounds for treating cancer and methods of use thereof
  申请人：MCMASTER UNIVERSITY

  公开号：US10576056B2

  公开（公告）日：2020-03-03

  Two isoforms of thyroid receptor alpha (THRα1 and THRα2) have been found to be associated with the growth of cancer. Use of inhibitors of THRα1 (Formula I) and/or agonists of THRα2 (Formula II) in the treatment of such cancers is disclosed. Treatment of other disorders associated with such receptors is also contemplated, as is the use of diagnostic methods for predicting therapeutic outcomes based on the levels of expression of THRα1 and THRaα2 in a tissue sample.

  已发现甲状腺受体α的两种异构体（THRα1 和 THRα2）与癌症的生长有关。本研究公开了 THRα1 的抑制剂（式 I）和/或 THRα2 的激动剂（式 II）在治疗此类癌症中的应用。此外，还考虑了与此类受体相关的其他疾病的治疗，以及根据组织样本中 THRα1 和 THRaα2 的表达水平预测治疗结果的诊断方法的使用。
• COMPOUNDS FOR USE IN TREATING CANCER
  申请人：McMaster University

  公开号：EP3393466B1

  公开（公告）日：2021-02-03
• COMPOUNDS FOR TREATING CANCER
  申请人：McMaster University

  公开号：US20200163930A1

  公开（公告）日：2020-05-28

  The present application relates to methods of using compounds of Formulae (I) and (II): for treatment of various cancers. The application further relates to pharmaceutical compositions and uses comprising the compounds of the application.
• Identification and Characterization of Potential Impurities of Dronedarone Hydrochloride
  作者：M. Mahender、M. Saravanan、Ch. Sridhar、E. R. R. Chandrashekar、L. Jaydeep Kumar、A. Jayashree、Rakeshwar Bandichhor

  DOI：10.1021/op400190b

  日期：2014.1.17

  Six potential process related impurities were detected during the impurity profile study of an antiarrhythmic drug substance, Dronedarone (1). Simple high performance liquid chromatography and liquid chromatography-mass spectrometry methods were used for the detection of these process impurities. Based on the synthesis and spectral data (MS, IR, H-1 NMR, C-13 NMR, and DEPT), the structures of these impurities were characterized as 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran (impurity I); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide (impurity II); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide (impurity III); N-2-propyl-3-[4-(3-dibutylaminopropoxy)benzoyl]benzofuran-5-yl}-methanesulfonamide (impurity IV); N-(2-butyl-3-(4-(3(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-formamide (impurity V); and (2-butyl-5-((3-(dibutylamino)propyl)amino)benzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone (impurity VI). The synthesis and characterization of these impurities are discussed in detail.