4-ethyl-7-hydroxy-6-methylbenzopyran-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: 4-ethyl-7-hydroxy-6-methylbenzopyran-2-one
• 英文别名: 4-Ethyl-7-hydroxy-6-methylchromen-2-one；4-ethyl-7-hydroxy-6-methylchromen-2-one
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: ZCVNPFAOKDILCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-7-hydroxy-6-methylbenzopyran-2-one 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 6,9-dimethyl-4-ethyl-2H-furo[2,3-h]-1-benzopyran-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel trimethylangelicin analogues targeting nuclear factor kB (NF-kB)

  摘要：

  A series of trimethylangelicin (TMA) derivatives were designed and synthesized to overcome the unwanted effects of TMA, promising agent for treatment of inflammation-related diseases and other pathologies, such as cystic fibrosis. The new generation TMA analogues bore hindered substituents at the 4 position in order to minimize or avoid the photoreactions with DNA. Among them, the 4-isopropyl-6-ethyl derivative 23 exhibited TMA-like inhibitory activity on NF-kappa B/DNA interactions but it proved unable to photoreact with pyrimidine bases of DNA, nor to induce any other DNA damage. The isopropyl analogue 23 was proven to lack mutagenicity when assayed through Ames test and exhibited no anti proliferative activity on cystic fibrosis IB3-1 cells, displaying at the same time inhibition of the TNF-alpha induced release of the NF-kappa B regulated PDGF-B chain, IL-10, IL-15, IL-17 and IFN-gamma. Therefore compound 23 deserves further assay to determine its anti-inflammatory properties, since it lacks photoreaction properties and mutagenicity-related side effects. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.080
• 作为产物：
  描述：

  4-甲基间苯二酚 、 丙酰乙酸乙酯 在 硫酸 作用下， 反应 1.0h， 以73%的产率得到4-ethyl-7-hydroxy-6-methylbenzopyran-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel trimethylangelicin analogues targeting nuclear factor kB (NF-kB)

  摘要：

  A series of trimethylangelicin (TMA) derivatives were designed and synthesized to overcome the unwanted effects of TMA, promising agent for treatment of inflammation-related diseases and other pathologies, such as cystic fibrosis. The new generation TMA analogues bore hindered substituents at the 4 position in order to minimize or avoid the photoreactions with DNA. Among them, the 4-isopropyl-6-ethyl derivative 23 exhibited TMA-like inhibitory activity on NF-kappa B/DNA interactions but it proved unable to photoreact with pyrimidine bases of DNA, nor to induce any other DNA damage. The isopropyl analogue 23 was proven to lack mutagenicity when assayed through Ames test and exhibited no anti proliferative activity on cystic fibrosis IB3-1 cells, displaying at the same time inhibition of the TNF-alpha induced release of the NF-kappa B regulated PDGF-B chain, IL-10, IL-15, IL-17 and IFN-gamma. Therefore compound 23 deserves further assay to determine its anti-inflammatory properties, since it lacks photoreaction properties and mutagenicity-related side effects. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.080

文献信息

• IRE-1alpha INHIBITORS
  申请人：MannKind Corporation

  公开号：US20150141424A1

  公开（公告）日：2015-05-21

  Compounds which directly inhibit IRE-1α activity in vitro, prodrugs, and pharmaceutically acceptable salts thereof. Such compounds and prodrugs are useful for treating diseases associated with the unfolded protein response or with regulated IRE1-dependent decay (RIDD) and can be used as single agents or in combination therapies.

  在体外直接抑制IRE-1α活性的化合物、前药及其药学上可接受的盐。这些化合物和前药可用于治疗与未折叠蛋白应答或受调节的IRE1依赖性降解（RIDD）相关的疾病，并可作为单一药物或联合治疗的组合疗法。
• IRE-1ALPHA INHIBITORS
  申请人：Shanghai Fosun Pharmaceutical Industrial Development Co. Ltd.

  公开号：US20170326104A1

  公开（公告）日：2017-11-16

  Compounds which directly inhibit IRE-1α activity in vitro, prodrugs, and pharmaceutically acceptable salts thereof. Such compounds and prodrugs are useful for treating diseases associated with the unfolded protein response or with regulated IRE1-dependent decay (RIDD) and can be used as single agents or in combination therapies.
• US9040714B2
  申请人：——

  公开号：US9040714B2

  公开（公告）日：2015-05-26
• US9693992B2
  申请人：——

  公开号：US9693992B2

  公开（公告）日：2017-07-04
• US9867803B2
  申请人：——

  公开号：US9867803B2

  公开（公告）日：2018-01-16