4-(1-(3-nitrobenzyl)-1H-benzo[d]imidazol-2-yl)thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(1-(3-nitrobenzyl)-1H-benzo[d]imidazol-2-yl)thiazole
• 英文别名: 4-[1-[(3-Nitrophenyl)methyl]benzimidazol-2-yl]-1,3-thiazole；4-[1-[(3-nitrophenyl)methyl]benzimidazol-2-yl]-1,3-thiazole
• 化学式: C₁₇H₁₂N₄O₂S
• 分子量: 336.374
• InChiKey: KGENDYSSTCNTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 sodium metabisulfite 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(1-(3-nitrobenzyl)-1H-benzo[d]imidazol-2-yl)thiazole
  参考文献：
  名称：

  新型苯并咪唑衍生物和类似物靶向NLRP3炎性小体的合成与生物学评估。

  摘要：

  合成了一系列噻唑的苯并[d]咪唑类似物，并评估了它们对炎性体NLRP3（核苷酸结合结构域富含亮氨酸的重复序列，含有蛋白质家族，含有pyrin结构域的家族3，也称为冻菌素或NALP3）的抗炎活性。 。通过产生IL-1β鉴定了两种先导化合物TBZ-09和TBZ-21。在第二轮生物学评估中，以铅为基础，又合成了34种化合物，并研究了它们的体外抗炎活性。几种化合物被鉴定为可以以剂量依赖的方式降低IL-1β表达的抗炎药。初步的构效关系也总结在这里。

  DOI：

  10.3390/molecules22020213

文献信息

• Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents
  作者：Chao Zhang、Bo Zhong、Simin Yang、Liangkun Pan、Siwang Yu、Zhongjun Li、Shuchun Li、Bin Su、Xiangbao Meng

  DOI：10.1016/j.bmc.2015.03.085

  日期：2015.7

  Thiabendazole, already approved by FDA for oral use as an anti-fungal and anti-helminthic drug since 1967, has recently been repurposed as a vascular disrupting agent. By optimization of the structure of the lead compound, we successfully identified compound TBZ-19 and the new derivative is over 100-fold more potent than the lead compound against the growth of four different cell lines ( A549, HCT-116, HepG2 and HUVECs). The most potent two candidates TBZ-07 and TBZ-19, exhibiting moderate inhibitory cell proliferation activity, were also verified as anti-angiogenesis and vascular disrupting agents. Therefore, TBZ-07 and TBZ-19 would be promising candidates with vasculature targeting activity and merit further development. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives and Analogs Targeting the NLRP3 Inflammasome
  作者：Liangkun Pan、Nan Hang、Chao Zhang、Yu Chen、Shuchun Li、Yang Sun、Zhongjun Li、Xiangbao Meng

  DOI：10.3390/molecules22020213

  日期：——

  synthesized and their antiinflammatory activities toward NLRP3 (nucleotide-binding domain leucine-rich repeat containing protein family，pyrin domain-containing 3，also known as cryopyrin or NALP3) inflammasome were evaluated in vitro. Two lead compounds, TBZ-09 and TBZ-21, were identified by antiproduction of IL-1β. In the second round of biological evaluation, based on the lead, 34 more compounds were synthesized

  合成了一系列噻唑的苯并[d]咪唑类似物，并评估了它们对炎性体NLRP3（核苷酸结合结构域富含亮氨酸的重复序列，含有蛋白质家族，含有pyrin结构域的家族3，也称为冻菌素或NALP3）的抗炎活性。 。通过产生IL-1β鉴定了两种先导化合物TBZ-09和TBZ-21。在第二轮生物学评估中，以铅为基础，又合成了34种化合物，并研究了它们的体外抗炎活性。几种化合物被鉴定为可以以剂量依赖的方式降低IL-1β表达的抗炎药。初步的构效关系也总结在这里。