7-Azido-3,4-dimethylchromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-Azido-3,4-dimethylchromen-2-one
• 英文别名: 7-azido-3,4-dimethylchromen-2-one
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: JATLCRWNILJCFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-β-(prop-2-yn-1-yloxy)-dihydroartemisinin 、 7-Azido-3,4-dimethylchromen-2-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以39.6%的产率得到3,4-dimethyl-7-((4-((10S)-dihydroartemisin-10-oxy)-methyl)-1H-1,2,3-triazol-1-yl)-2H-1-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

  摘要：

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.005
• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 盐酸 、 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 生成 7-Azido-3,4-dimethylchromen-2-one
  参考文献：
  名称：

  Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

  摘要：

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.005

文献信息

• CHEMICAL CROSSLINKERS AND COMPOSITIONS THEREOF
  申请人：Nguyen Mark Quang

  公开号：US20140249319A1

  公开（公告）日：2014-09-04

  Chemical crosslinkers and methods of their synthesis are disclosed.

  化学交联剂及其合成方法已被披露。
• CLEAVABLE DRUG CONJUGATES, COMPOSITIONS THEREOF AND METHODS OF USE
  申请人：NGUYEN MARK QUANG

  公开号：US20140294851A1

  公开（公告）日：2014-10-02

  Base-labile crosslinkers, base-labile conjugates comprising such crosslinkers, methods of their synthesis and use are disclosed.

  揭示了一种含有易碱性交联剂的易碱性共轭物、其合成和使用方法。
• METHODS OF USING CLEAVABLE DRUG CONJUGATES AND COMPOSITIONS THEREOF
  申请人：Nguyen Mark Quang

  公开号：US20160143937A1

  公开（公告）日：2016-05-26

  Methods of synthesizing and using base-labile drug conjugates and compositions thereof are disclosed.

  本发明揭示了合成和使用碱性不稳定药物结合物及其组合物的方法。
• US9295731B2
  申请人：——

  公开号：US9295731B2

  公开（公告）日：2016-03-29
• US9695189B2
  申请人：——

  公开号：US9695189B2

  公开（公告）日：2017-07-04