5-(4-aminophenyl)-3H-1,2-dithiole-3-thione | 214557-38-7

• 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: 5-(4-aminophenyl)-3H-1,2-dithiole-3-thione
• 英文别名: 5-(4-Amino-phenyl)-[1,2]dithiole-3-thione；5-(4-aminophenyl)dithiole-3-thione
• CAS: 214557-38-7
• 化学式: C₉H₇NS₃
• 分子量: 225.359
• InChiKey: PHJNNFGXRTVFEI-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-aminophenyl)-3H-1,2-dithiole-3-thione 在 苯甲腈 N-氧化物 作用下， 以65%的产率得到5-(p-aminophenyl)-1,2-dithiole-3-one
  参考文献：
  名称：

  Cholett, Marylene; Legouin, Beatrice; Burgot, Jean-Louis, Journal of the Chemical Society. Perkin transactions II, 1998, # 10, p. 2227 - 2232

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-(4-aminophenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Derivatives of 4- or 5-aminosalicylic acid

  摘要：

  本发明提供了4-或5-氨基水杨酸的新衍生物，以及含有这些4-或5-氨基水杨酸衍生物作为活性成分的药物组合物，用于治疗肠病，如炎症性肠病（IBD）和肠易激综合症（IBS）以及预防/治疗结肠癌。更具体地，这些衍生物包含一个通过偶氮基、酯基、酐基、硫酯基或酰胺键连接到4-或5-氨基水杨酸分子上的硫化氢释放基团。此外，本发明还提供了制备这些化合物的方法以及它们用于治疗IBD和IBS以及预防/治疗结肠癌的应用。

  公开号：

  US20060270635A1

文献信息

• Derivaitves of 4-Or 5-Aminosalicylic Acid
  申请人：Wallace John L.

  公开号：US20080207564A1

  公开（公告）日：2008-08-28

  The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS) and for the prevention/treatment of colon cancer. More particularly, these derivatives comprise a hydrogen sulfide releasing moiety linked via an azo, an ester, an anhydride, a thioester or an amide linkage to a molecule of 4- or 5-aminosalicylic acid. Furthermore, the present invention provides a process for preparing these compounds and their use for treating IBD and IBS and the prevention/treatment of colon cancer.

  本发明提供了4-或5-氨基水杨酸的新衍生物，以及含有这些4-或5-氨基水杨酸衍生物作为活性成分的药物组合物，用于治疗肠道疾病，如炎症性肠病（IBD）和肠易激综合征（IBS），以及预防/治疗结肠癌。更具体地说，这些衍生物包括通过偶氮键，酯键，酸酐键，硫酯键或酰胺键连接到4-或5-氨基水杨酸分子的硫化氢释放基团。此外，本发明提供了制备这些化合物的方法以及它们用于治疗IBD和IBS以及预防/治疗结肠癌的用途。
• Synthesis of Amino-ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets
  作者：Michael Pluth、Matthew Hammers、Loveprit Singh、Leticia Montoya、Alan Moghaddam

  DOI：10.1055/s-0035-1560603

  日期：——

  As additional physiological functions of hydrogen sulfide (H2S) are discovered, developing practical methods for exogenous H2S delivery is important. In particular, nonsteroidal anti-inflammatory drugs (NSAIDs) functionalized with H2S-releasing anethole dithiolethione (ADT-OH) through ester bonds are being investigated for their combined anti-inflammatory and antioxidant potential. The chemical robustness

  随着硫化氢 (H2S) 的其他生理功能的发现，开发外源 H2S 输送的实用方法非常重要。特别是，正在研究通过酯键与释放 H2S 的茴香脑二硫代硫酮 (ADT-OH) 功能化的非甾体抗炎药 (NSAID) 的联合抗炎和抗氧化潜力。然而，药物和 H2S 输送成分之间连接的化学稳定性是这些化合物中关键且可控的连接。由于酯类容易水解，特别是在口服给药应用中的胃酸等酸性条件下，我们在此报告了氨基-ADT (ADT-NH2 ) 的简单合成，并为药物萘普生和 ADT-NH2 成功衍生化提供了条件。丙戊酸。使用紫外可见光谱和高效液相色谱分析，我们证明酰胺官能化 ADT 衍生物比酯官能化 ADT 衍生物更耐水解。
• DERIVATIVES OF 4- OR 5-AMINOSALICYLIC ACID
  申请人：Wallace John L.

  公开号：US20090233886A1

  公开（公告）日：2009-09-17

  The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS) and for the prevention/treatment of colon cancer. More particularly, these derivatives comprise a hydrogen sulfide releasing moiety linked via an azo, an ester, an anhydride, a thioester or an amide linkage to a molecule of 4- or 5-aminosalicylic acid. Furthermore, the present invention provides a process for preparing these compounds and their use for treating IBD and IBS and the prevention/treatment of colon cancer.

  本发明提供了4-或5-氨基水杨酸的新衍生物，以及包含这些4-或5-氨基水杨酸衍生物作为活性成分的制药组合物，用于治疗肠道疾病，如炎症性肠病（IBD）和肠易激综合征（IBS），以及预防/治疗结肠癌。更具体地说，这些衍生物包括通过偶氮，酯，酸酐，硫酯或酰胺连接到4-或5-氨基水杨酸分子上的释放硫化氢的基团。此外，本发明提供了一种制备这些化合物的方法以及它们用于治疗IBD和IBS以及预防/治疗结肠癌的用途。
• SALTS OF TRIMEBUTINE AND N-DESMETHYL TRIMEBUTINE
  申请人：WALLACE L. JOHN

  公开号：US20070275905A1

  公开（公告）日：2007-11-29

  Unique salts of trimebutine and N-monodesmethyl trimebutine, and their corresponding stereoisomers, having improved analgesic properties useful in the treatment of visceral pain are provided. The salts of the present invention are particularly useful in the treatment of conditions characterized by abdominal pain, such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS), diabetic gastroparesis, and dyspepsia.

  本发明提供了三甲叉胺和N-单去甲基三甲叉胺的独特盐及其对应的立体异构体，具有改善的镇痛特性，可用于治疗内脏疼痛。本发明的盐尤其适用于治疗腹部疼痛症状，例如炎症性肠病（IBD）和肠易激综合征（IBS）、糖尿病性胃轻瘫和消化不良等。
• Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
  作者：Zi-Long Song、Feifei Bai、Baoxin Zhang、Jianguo Fang

  DOI：10.1021/acs.jafc.9b06360

  日期：2020.2.19

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.