5-naphthalen-1-yl-3H-[1,3,4]thiadiazole-2-thione | 28813-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-naphthalen-1-yl-3H-[1,3,4]thiadiazole-2-thione
• 英文别名: 2α-Naphthyl-1,3,4-thiadiazoline-5-thione；5-naphthalen-1-yl-3H-1,3,4-thiadiazole-2-thione
• CAS: 28813-62-9
• 化学式: C₁₂H₈N₂S₂
• 分子量: 244.341
• InChiKey: ATKAZYRTMSWANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯 、 5-naphthalen-1-yl-3H-[1,3,4]thiadiazole-2-thione 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以91%的产率得到2-(naphthalen-1-yl)-5-(phenylthio)-1,3,4-thiadiazole
  参考文献：
  名称：

  铜催化杂环硫醇与芳基碘化物的C–S交叉偶联

  摘要：

  据报道，铜催化的杂环硫醇与芳基碘化物的交叉偶联。反应在120℃下在CuI（5mol％），1，10-菲咯啉（10mol％）和K 2 CO 3（1.3当量）的存在下在DMF中进行。以高选择性和高产率制备了各种杂环硫化物。

  DOI：

  10.1016/j.tet.2011.02.064
• 作为产物：
  描述：

  二硫化碳 、 naphthalene-1-carbohydrazonic acid amide 以 乙醇 为溶剂， 反应 2.0h， 生成 5-naphthalen-1-yl-3H-[1,3,4]thiadiazole-2-thione
  参考文献：
  名称：

  Kubota,S. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 8, p. 1696 - 1698

  摘要：

  DOI：

文献信息

• [EN] INHIBITORS OF HUMAN 15-LIPOXYGENASE-1<br/>[FR] INHIBITEURS DE LA 15-LIPOXYGÉNASE-1 HUMAINE
  申请人：US HEALTH

  公开号：WO2011028651A1

  公开（公告）日：2011-03-10

  Disclosed are inhibitors of human 15 lipoxygenase 1, for example, of formula (I), wherein R1, R2, R3, R4, X, Y, and Z are as defined herein, that are useful in treating a 15-lipoxygenase mediated disease or disorder, e.g., prostate cancer. Also disclosed is a composition comprising a pharmaceutically suitable carrier and at least one compound of the invention, and a method of treating prostate cancer in a mammal.

  本文披露了人类15-脂氧合酶1的抑制剂，例如式（I）中的抑制剂，其中R1、R2、R3、R4、X、Y和Z如本文所定义，这些抑制剂对治疗15-脂氧合酶介导的疾病或紊乱，例如前列腺癌，具有有用性。还披露了一种包含药用载体和本发明中至少一种化合物的组合物，以及一种治疗哺乳动物前列腺癌的方法。
• Discovery of Potent and Selective Inhibitors of Human Reticulocyte 15-Lipoxygenase-1
  作者：Ganesha Rai、Victor Kenyon、Ajit Jadhav、Lena Schultz、Michelle Armstrong、J. Brian Jameson、Eric Hoobler、William Leister、Anton Simeonov、Theodore R. Holman、David J. Maloney

  DOI：10.1021/jm1008852

  日期：2010.10.28

  There are a variety of lipoxygenases in the human body (hLO), each having a distinct role in cellular biology. Human reticulocyte 15-lipoxygenase-1 (15-hLO-1), which catalyzes the dioxygenation of 1,4-cis,cis-pentadiene-containing polyunsaturated fatty acids, is implicated in a number of diseases including cancer, atherosclerosis, and neurodegenerative conditions. Despite the potential therapeutic relevance of this target, few inhibitors have been reported that are both potent and selective. To this end, we have employed a quantitative high-throughput (qHTS) screen against similar to 74000 small molecules in search of reticulocyte 15-hLO-1 selective inhibitors. This screen led to the discovery of a novel chemotype for 15-hLO-1 inhibition, which displays nM potency and is > 7500-fold selective against the related isozymes, 5-hLO, platelet 12-hLO, epithelial 15-hLO-2, ovine cyclooxygenase-1, and human cyclooxygenase-2. In addition, kinetic experiments were performed which indicate that this class of inhibitor is tight binding, reversible, and appears not to reduce the active-site ferric ion.
• US6080772A
  申请人：——

  公开号：US6080772A

  公开（公告）日：2000-06-27
• Kubota,S. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 8, p. 1696 - 1698
  作者：Kubota,S. et al.

  DOI：——

  日期：——
• Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides
  作者：Liang-Feng Niu、Yan Cai、Chao Liang、Xin-Ping Hui、Peng-Fei Xu

  DOI：10.1016/j.tet.2011.02.064

  日期：2011.4

  A copper-catalyzed cross-coupling of heterocyclic thiols with aryl iodides is reported. The reaction was carried out in the presence of CuI (5 mol %), 1,10-phenanthroline (10 mol %) and K2CO3 (1.3 equiv) in DMF at 120 °C. A variety of heterocyclic sulfides were prepared in high selectivities and yields.

  据报道，铜催化的杂环硫醇与芳基碘化物的交叉偶联。反应在120℃下在CuI（5mol％），1，10-菲咯啉（10mol％）和K 2 CO 3（1.3当量）的存在下在DMF中进行。以高选择性和高产率制备了各种杂环硫化物。