1,4-diazabicyclo[2.2.2]octane (4-nitrophenyl)carbamodithioate | 1442636-40-9

• 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: 1,4-diazabicyclo[2.2.2]octane (4-nitrophenyl)carbamodithioate
• CAS: 1442636-40-9
• 化学式: C₆H₁₂N₂*C₇H₆N₂O₂S₂
• 分子量: 326.444
• InChiKey: ZIAHBUHRBUFZBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,4-diazabicyclo[2.2.2]octane (4-nitrophenyl)carbamodithioate 在 三光气 、 potassium hydroxide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 2-(1-cyano-1-carboxylic acid methyl ester)-3-N-(4-nitrophenyl)-1,3-thiazol-4-one
  参考文献：
  名称：

  Design, synthesis, and nematicidal activities of novel 1,3-thiazin(thiazol)-4-one derivatives against Meloidogyne incognita

  摘要：

  Four series of novel 1,3-thiazin(thiazol)-4-one derivatives were synthesized by Suzuki coupling. Preliminary bioassays showed that most of the synthesized compounds exhibited good inhibitory activity in vivo against root-knot nematodes, Meloidogyne spp. at 20 mg L−1. Among the tested compounds, we found that two compounds displayed 46.4% and 41.4% inhibitory activity even at 1 mg L−1, respectively.

  DOI：

  10.1177/1747519819857506
• 作为产物：
  描述：

  三乙烯二胺 、 二硫化碳 、 4-硝基苯胺 以 丙酮 为溶剂， 以90%的产率得到1,4-diazabicyclo[2.2.2]octane (4-nitrophenyl)carbamodithioate
  参考文献：
  名称：

  使用三光气和助溶剂简便而多功能地合成烷基和芳基异硫氰酸酯

  摘要：

  摘要 以(CH3)2CO-CS2 为共溶剂，三光气为脱氢硫化剂，开发了一种温和高效的二硫代氨基甲酸酯将烷基胺和芳基胺转化为异硫氰酸酯的方法。与报道的方法相比，高产率、温和的反应条件和优异的官能团兼容性使其成为制备异硫氰酸酯的通用合成方法。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要

  DOI：

  10.1080/00397911.2013.783600

文献信息

• Synthesis, structure–activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase
  作者：Fanxun Zeng、Tiantian Qi、Chunyan Li、Tingfang Li、Honglin Li、Shiliang Li、Lili Zhu、Xiaoyong Xu

  DOI：10.1039/c7md00081b

  日期：——

  series of 4-thiazolidinone derivatives were synthesized and evaluated as novel human dihydroorotate dehydrogenase (hDHODH) inhibitors. Compounds 26 and 31 displayed IC50 values of 1.75 and 1.12 μM, respectively. The structure–activity relationship was summarized. Further binding mode analysis revealed that compound 31 could form a hydrogen bond with Tyr38 and a water-mediated hydrogen bond with Ala55,

  合成了一系列的4-噻唑烷酮衍生物，并作为新型人二氢乳清酸脱氢酶（h DHODH）抑制剂进行了评估。化合物26和31的IC 50值分别为1.75和1.12μM。构效关系进行了总结。进一步的结合模式分析表明，化合物31可以与Tyr38形成氢键，并与Ala55形成水介导的氢键，这对于维持该系列化合物的生物活性可能是必需的。R上苯基对位或间位的进一步结构优化将导致鉴定更有效的hDHODH抑制剂。
• Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita
  作者：Yaning Chang、Jingwei Zhang、Xiulei Chen、Zhong Li、Xiaoyong Xu

  DOI：10.1016/j.bmcl.2016.12.065

  日期：2017.6

  Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0 mg L-1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0 mg L-1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further. (C) 2016 Elsevier Ltd. All rights reserved.