N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-(prop-2-enoxy)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-N-[(trifluoroacetyl)glycyl]amine | 1208314-87-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-(prop-2-enoxy)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-N-[(trifluoroacetyl)glycyl]amine
• 英文别名: N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-(prop-2-enoxy)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-[(trifluoroacetyl)amino]acetamide
• CAS: 1208314-87-7
• 化学式: C₂₆H₂₇F₃N₂O₆S
• 分子量: 552.571
• InChiKey: TWWFXZCNPXWZHM-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  秋水仙碱 在 盐酸 、 水 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 41.0h， 生成 N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-(prop-2-enoxy)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-N-[(trifluoroacetyl)glycyl]amine
  参考文献：
  名称：

  [EN] NOVEL COLCHICINE DERIVATIVES, METHODS AND USES THEREOF
  [FR] NOUVEAUX DÉRIVÉS DE COLCHICINE, LEURS PROCÉDÉS ET UTILISATIONS

  摘要：

  本发明涉及秋水仙碱衍生物、其制备方法及其用于治疗癌症的应用。在某些实施例中，秋水仙碱衍生物包括公式(I)的化合物，其中Z是O或S；R1选自H、卤素基团、取代或不取代的烃基团或取代或不取代的杂原子基团；R2和R3各自独立地选自H、卤素基团、取代或不取代的烃基团、取代或不取代的杂原子基团、取代或不取代的碳环基团、取代或不取代的杂环基团、取代或不取代的芳香基团或取代或不取代的杂芳香基团；R选自H或取代或不取代的烃基团，但R、R2和R3为甲基基团时，R1不是-COCH3。

  公开号：

  WO2011022805A1

文献信息

• Derivatives of thiocolchicine and its applications to CEM cells treatment using 19F Magnetic Resonance ex vivo
  作者：Dorota Bartusik、Boguslaw Tomanek、Erika Lattová、Hélène Perreault、Jack Tuszynski、Gino Fallone

  DOI：10.1016/j.bioorg.2009.10.002

  日期：2010.2

  It was shown, that cultured ex vivo human T-Lymphoblastoid (CEM) cells respond to synthesized thiocolchicine and fluorine thiocolchicine derivatives. The preparation of derivatives with substitution at C-3 and C-7 is described. All compounds were used at concentration from 1 nM to 1000 nM. Inhibitory effects of these compounds were examined in the three-dimensional (3-D) culture and cells morphology during treatment was monitored using 9.4 T MRI system. We performed studies of these compounds in CEM cells ex vivo using H-1 and F-19 Magnetic Resonance Imaging (MRI), F-19 Magnetic Resonance Spectroscopy (MRS), High Performance Liquid Chromatography coupled with Ultra Violet (HPLC-UV) and Electron Impact Mass Spectrometry (EIMS). The results of the multi-technique approach are consistent with the fact that the new derivatives are more efficient than colchicine and thiocolchicine ex vivo. Crown Copyright (C) 2009 Published by Elsevier Inc. All rights reserved.
• WO2020000109A5
  申请人：——

  公开号：WO2020000109A5

  公开（公告）日：2022-06-22
• [EN] NOVEL COLCHICINE DERIVATIVES, METHODS AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE COLCHICINE, LEURS PROCÉDÉS ET UTILISATIONS
  申请人：ALBERTA HEALTH SERVICES

  公开号：WO2011022805A1

  公开（公告）日：2011-03-03

  The invention relates to colchicine derivatives, methods and uses thereof for treatment of cancer. In certain embodiments, the colchicine derivative comprises a compound of formula (I), wherein Z is O or S; R1 is selected fro H, a halo group, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterogeneous group; R2 and R3 are each independently selected from H, a halo group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic; R is selected from H or a substituted or unsubstituted hydrocarbon group, with the proviso that when R, R2 and R3 are methyl groups, R1 is not -COCH3.

  本发明涉及秋水仙碱衍生物、其制备方法及其用于治疗癌症的应用。在某些实施例中，秋水仙碱衍生物包括公式(I)的化合物，其中Z是O或S；R1选自H、卤素基团、取代或不取代的烃基团或取代或不取代的杂原子基团；R2和R3各自独立地选自H、卤素基团、取代或不取代的烃基团、取代或不取代的杂原子基团、取代或不取代的碳环基团、取代或不取代的杂环基团、取代或不取代的芳香基团或取代或不取代的杂芳香基团；R选自H或取代或不取代的烃基团，但R、R2和R3为甲基基团时，R1不是-COCH3。