4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)-N-(1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)butyramide | 1356995-88-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)-N-(1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)butyramide
• 英文别名: 4-(3-oxo-benzo[d][1,2]selenazol-2-yl)-N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranosyl)-butyramide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-(3-oxo-1,2-benzoselenazol-2-yl)butanoylamino]oxan-2-yl]methyl acetate
• CAS: 1356995-88-4
• 化学式: C₂₅H₃₀N₂O₁₁Se
• 分子量: 613.48
• InChiKey: YZUQFAROCPSMBL-REXJZNOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)-N-(1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)butyramide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)-N-(1-deoxy-β-D-glucopyranosyl)butyramide
  参考文献：
  名称：

  [EN] COMPOUNDS TARGETING THE CELL INVASION PROTEIN COMPLEX, THEIR PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF
  [FR] COMPOSÉS CIBLANT LE COMPLEXE PROTÉIQUE D'INVASION CELLULAIRE, LEURS COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本申请涉及到I式化合物（I）以及它们在抑制AKT-1、FAK和PKCα中至少一种方面的使用，以及在治疗和/或预防转移性疾病方面的使用。

  公开号：

  WO2013059927A1
• 作为产物：
  描述：

  双（2-羧基苯基）二硒化物 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)-N-(1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)butyramide
  参考文献：
  名称：

  Synthesis and biological activity of novel organoselenium derivatives targeting multiple kinases and capable of inhibiting cancer progression to metastases

  摘要：

  The present study reports synthesis and biological activity of novel benzoisoselenazolone compounds derived from ebselen and conjugated to a sugar molecule. Cell proliferation assay using cancer cells combined with in vitro biochemical assays revealed that benzoisoselenazolone 2d, 5a, and 6a exerted anti-proliferative activity, which correlated with selective in vitro inhibition of focal adhesion kinase, AKT-1, and protein kinase C-alpha. Active molecules were able to significantly inhibit cell migration and invasion in vitro compared to cells treated with the vehicle alone or ebselen. Moreover, in vivo anticancer activity focusing on lead compound 2d and using an invasive human breast cancer orthotopic mouse model revealed a potent anti-metastatic activity at well-tolerated doses. In summary, these novel benzoisoselenazolones we report herein target multiple kinases with established roles in cancer progression and possess anti-invasive and anti-metastatic activity in preclinical models supporting a potential for therapeutic application for human disease. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.006

文献信息

• [EN] COMPOUNDS TARGETING THE CELL INVASION PROTEIN COMPLEX, THEIR PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS CIBLANT LE COMPLEXE PROTÉIQUE D'INVASION CELLULAIRE, LEURS COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ROYAL INST FOR THE ADVANCEMENT OF LEARNING MCGILL UNIVERSITY

  公开号：WO2013059927A1

  公开（公告）日：2013-05-02

  The present application relates to the compounds of formula I (I) as well as their use for inhibiting at least one of AKT-1, FAK and PKCα and in the treatment and/or prevention of metastatic diseases.

  本申请涉及到I式化合物（I）以及它们在抑制AKT-1、FAK和PKCα中至少一种方面的使用，以及在治疗和/或预防转移性疾病方面的使用。
• Synthesis and biological activity of novel organoselenium derivatives targeting multiple kinases and capable of inhibiting cancer progression to metastases
  作者：Krikor Bijian、Zhongwei Zhang、Bin Xu、Su Jie、Bo Chen、Shengbiao Wan、JianHui Wu、Tao Jiang、Moulay A. Alaoui-Jamali

  DOI：10.1016/j.ejmech.2011.12.006

  日期：2012.2

  The present study reports synthesis and biological activity of novel benzoisoselenazolone compounds derived from ebselen and conjugated to a sugar molecule. Cell proliferation assay using cancer cells combined with in vitro biochemical assays revealed that benzoisoselenazolone 2d, 5a, and 6a exerted anti-proliferative activity, which correlated with selective in vitro inhibition of focal adhesion kinase, AKT-1, and protein kinase C-alpha. Active molecules were able to significantly inhibit cell migration and invasion in vitro compared to cells treated with the vehicle alone or ebselen. Moreover, in vivo anticancer activity focusing on lead compound 2d and using an invasive human breast cancer orthotopic mouse model revealed a potent anti-metastatic activity at well-tolerated doses. In summary, these novel benzoisoselenazolones we report herein target multiple kinases with established roles in cancer progression and possess anti-invasive and anti-metastatic activity in preclinical models supporting a potential for therapeutic application for human disease. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.