5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1H-indol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1H-indol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one
• 英文别名: 3-[2,4-bis(phenylmethoxy)-5-propan-2-ylphenyl]-4-(1H-indol-5-yl)-1H-1,2,4-triazol-5-one
• 化学式: C₃₃H₃₀N₄O₃
• 分子量: 530.626
• InChiKey: GHZCYLLZOCXYER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1H-indol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1H-indol-5-yl)-1H-1,2,4-triazol-5-one
  参考文献：
  名称：

  一种具有抗真菌与抗肿瘤双重作用的三唑酮类化合物及应用

  摘要：

  本发明公开了一种具有抗真菌与抗肿瘤双重作用的三唑酮类化合物，结构通式如下所示：各取代基定义详见说明书。本发明的三唑酮类化合物具有抗真菌与抗肿瘤双重作用，可以作为三唑酮类Hsp90抑制剂和Hsp90‑HDAC双靶点抑制剂，可以用作抗真菌与抗肿瘤的药物使用。

  公开号：

  CN113121505B
• 作为产物：
  描述：

  2,4-二苄氧基-5-异丙基苯甲醛 在 溶剂黄146 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1H-indol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  A tumor-targeted Ganetespib-zinc phthalocyanine conjugate for synergistic chemo-photodynamic therapy

  摘要：

  Therapeutic effects of photodynamic therapy (PDT) are limited by the selectivity of photosensitizer (PS). Herein, a novel tumor-targeted drug-PS conjugate (Gan-ZnPc) which integrated with zinc phthalocyanine (ZnPc) and Ganetespib has been developed. ZnPc is a promising PS with remarkable photosensitization ability. Ganetespib is a heat shock protein 90 (Hsp90) inhibitor with preferential tumor selectivity and conjugated to ZnPc as a tumor-targeted ligand. The multifunctional small molecule conjugate, Gan-ZnPc, could be bound to extracellular Hsp90 and then selectively internalized into the tumor cells, followed by the generation of abundant intracellular reactive oxygen species (ROS) upon irradiation. Besides, Gan-ZnPc can arrest cell proliferation and induce apoptosis by the inhibition of Hsp90. Herein, with combination of the inhibition of Hsp90 and the generation of cytotoxic ROS, Gan-ZnPc implements tumor selectivity, concentrated PDT and chemotherapy in a synergistic manner, which results in highly effective anti-tumor activity in vitro and in vivo. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.077

文献信息

• Triazole compounds that modulate Hsp90 activity
  申请人：Sun Lijun

  公开号：US20080176840A1

  公开（公告）日：2008-07-24

  The present invention relates to substituted triazole compounds and compositions comprising substituted triazole compounds. The invention further relates to methods of inhibiting the activity of Hsp90 in a subject in need thereof and methods for preventing or treating hyperproliferative disorders, such as cancer, in a subject in need thereof comprising administering to the subject a substituted triazole compound of the invention, or a composition comprising such a compound.

  本发明涉及替代三唑化合物和包含替代三唑化合物的组合物。该发明还涉及在需要的受试者中抑制Hsp90活性的方法，以及预防或治疗过度增殖性疾病，如癌症，的方法，包括向受试者施用本发明的替代三唑化合物或包含这种化合物的组合物。
• US8053456B2
  申请人：——

  公开号：US8053456B2

  公开（公告）日：2011-11-08
• 一种具有抗真菌与抗肿瘤双重作用的三唑酮类化合物及应用
  申请人：中国人民解放军海军军医大学

  公开号：CN113121505B

  公开（公告）日：2023-03-07

  本发明公开了一种具有抗真菌与抗肿瘤双重作用的三唑酮类化合物，结构通式如下所示：各取代基定义详见说明书。本发明的三唑酮类化合物具有抗真菌与抗肿瘤双重作用，可以作为三唑酮类Hsp90抑制剂和Hsp90‑HDAC双靶点抑制剂，可以用作抗真菌与抗肿瘤的药物使用。
• A tumor-targeted Ganetespib-zinc phthalocyanine conjugate for synergistic chemo-photodynamic therapy
  作者：Liangfeng Huang、Gaofei Wei、Xiaoqi Sun、Yali Jiang、Zeqian Huang、Yanjuan Huang、Yifeng Shen、Xiaoyu Xu、Yunhui Liao、Chunshun Zhao

  DOI：10.1016/j.ejmech.2018.03.077

  日期：2018.5

  Therapeutic effects of photodynamic therapy (PDT) are limited by the selectivity of photosensitizer (PS). Herein, a novel tumor-targeted drug-PS conjugate (Gan-ZnPc) which integrated with zinc phthalocyanine (ZnPc) and Ganetespib has been developed. ZnPc is a promising PS with remarkable photosensitization ability. Ganetespib is a heat shock protein 90 (Hsp90) inhibitor with preferential tumor selectivity and conjugated to ZnPc as a tumor-targeted ligand. The multifunctional small molecule conjugate, Gan-ZnPc, could be bound to extracellular Hsp90 and then selectively internalized into the tumor cells, followed by the generation of abundant intracellular reactive oxygen species (ROS) upon irradiation. Besides, Gan-ZnPc can arrest cell proliferation and induce apoptosis by the inhibition of Hsp90. Herein, with combination of the inhibition of Hsp90 and the generation of cytotoxic ROS, Gan-ZnPc implements tumor selectivity, concentrated PDT and chemotherapy in a synergistic manner, which results in highly effective anti-tumor activity in vitro and in vivo. (C) 2018 Elsevier Masson SAS. All rights reserved.