2-(2-methoxy-4-(5-thioxo-5H-1,2-dithiol-3-yl)phenoxy)acetic acid | 1155414-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methoxy-4-(5-thioxo-5H-1,2-dithiol-3-yl)phenoxy)acetic acid
• 英文别名: H2S-releasing peptide conjugate building block ADT；2-[2-methoxy-4-(5-sulfanylidenedithiol-3-yl)phenoxy]acetic acid
• CAS: 1155414-04-2
• 化学式: C₁₂H₁₀O₄S₃
• 分子量: 314.407
• InChiKey: OMBTXMCRLLPTOW-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  527.5±60.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-4-(5-thioxo-5H-1,2-dithiol-3-yl)phenoxy)acetic acid 在 3,3,3-膦三基三丙酸 作用下， 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 硫化氢
  参考文献：
  名称：

  Controlled release of hydrogen sulfide significantly reduces ROS stress and increases dopamine levels in transgenic C. elegans

  摘要：

  已经开发出一种新型的肽基系统，它展示出缓慢和持续的H₂S释放，从而减少过氧化氢诱导的氧化应激，并增加转基因C. elegans模型中的多巴胺水平。

  DOI：

  10.1039/c9cc05153h
• 作为产物：
  描述：

  methyl 2-[2-methoxy-4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]acetate 在 硫酸 、 溶剂黄146 作用下， 反应 1.5h， 以62.2%的产率得到2-(2-methoxy-4-(5-thioxo-5H-1,2-dithiol-3-yl)phenoxy)acetic acid
  参考文献：
  名称：

  Controlled release of hydrogen sulfide significantly reduces ROS stress and increases dopamine levels in transgenic C. elegans

  摘要：

  已经开发出一种新型的肽基系统，它展示出缓慢和持续的H₂S释放，从而减少过氧化氢诱导的氧化应激，并增加转基因C. elegans模型中的多巴胺水平。

  DOI：

  10.1039/c9cc05153h

文献信息

• Design, Synthesis and Biological Evaluations of Novel Conjugates of Danshensu, Tetramethylpyrazine and Hydrogen Sulfide Donors as Cardioprotective Agents
  作者：Chang-Jiang Xu、Hui-Xing Deng、Hai-Yun Chen、Qing-Bin Cui、Lu-Chen Shan、Pei Yu、Ye-Wei Sun、Yu-Qiang Wang

  DOI：10.14233/ajchem.2016.20101

  日期：——

  A series of molecular hybrids of Danshensu-tetramethylpyrazine-hydrogen sulfide donors have been synthesized and evaluated in vitro as potent antimyocardial ischemia agents. The pharmacological data demonstrated that compound DTA-2 exhibited the most potent protective activities against tert-butyl hydroperoxide (t-BHP) induced injury in H9c2 cells. Further study showed that DTA-2 exhibited better ROS-scavenging activity and mitochondria protective effect than its parental drug DTM, ACS48 and mixtures of these two. These results indicated that DTA-2 may work through a unique mechanism and may serve as a drug candidate for anti-myocardial ischemia therapy that require further study.

  一系列丹参酚-四甲基吡嗪-硫化氢供体的分子杂化物被合成并在体外评估为有效的抗心肌缺血药物。药理数据表明，化合物DTA-2对叔丁基过氧化氢（t-BHP）诱导的H9c2细胞损伤展现出最强的保护活性。进一步研究表明，DTA-2的清除活性氧（ROS）能力和线粒体保护效果优于其母药DTM、ACS48及这两者的混合物。这些结果表明，DTA-2可能通过独特机制发挥作用，并可能作为抗心肌缺血治疗的药物候选者，需进一步研究。
• [EN] COMPOSITIONS AND METHODS TO TREAT NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR TRAITER DES MALADIES NEURODÉGÉNÉRATIVES
  申请人：GEN HOSPITAL CORP

  公开号：WO2014015047A1

  公开（公告）日：2014-01-23

  The specification provides compositions and methods to treat neurodegenerative diseases.

  该规范提供了治疗神经退行性疾病的组成成分和方法。
• COMPOSITIONS AND METHODS TO TREAT NEURODEGENERATIVE DISEASES
  申请人：The General Hospital Corporation

  公开号：US20150209438A1

  公开（公告）日：2015-07-30

  The specification provides compositions and methods to treat neurodegenerative diseases.

  该规格说明提供了用于治疗神经退行性疾病的组合物和方法。
• [EN] NEW ANTICANCER COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTICANCERS
  申请人：SULFIDRIS S R L

  公开号：WO2009065926A3

  公开（公告）日：2009-07-30
• New aryldithiolethione derivatives as potent histone deacetylase inhibitors
  作者：Valerio Tazzari、Graziella Cappelletti、Manolo Casagrande、Elena Perrino、Luigi Renzi、Piero Del Soldato、Anna Sparatore

  DOI：10.1016/j.bmc.2010.05.011

  日期：2010.6.15

  A series of dithiolethione derivatives was synthesized and the in vitro HDAC inhibitory activity was tested. The most active compounds, 1 and 2, exhibited an IC50 in nM range with a strong hyperacetylation of histone H4 in A549 cells. The HDAC inhibitory activity comparable to that of SAHA and the inhibition of A549 cell proliferation suggest that these compounds are worthy of further studies as potential anticancer agents. (C) 2010 Elsevier Ltd. All rights reserved.