4-Azido-2-chlorobenzonitrile | 1200710-07-1

• 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: 4-Azido-2-chlorobenzonitrile
• 英文别名: 4-azido-2-chlorobenzonitrile
• CAS: 1200710-07-1
• 化学式: C₇H₃ClN₄
• 分子量: 178.581
• InChiKey: ZGAXEIQAZYPDEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙炔基吡啶 、 4-Azido-2-chlorobenzonitrile 在 copper(II) sulfate 、 维生素 C 作用下， 以 水 为溶剂， 反应 0.5h， 以85%的产率得到2-chloro-4-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)benzonitrile
  参考文献：
  名称：

  A comparison of novel organoiridium(III) complexes and their ligands as a potential treatment for prostate cancer

  摘要：

  A range of 1,4-substituted 2-pyridyl-N-phenyl triazoles were synthesised and evaluated for their anti proliferative properties against lymph node cancer of the prostate (LNCaP) and bone metastasis of prostate cancer (PC-3) cells. Excellent-to-low IC50 values were determined (5.6-250 mu M), and a representative group of 4 ligands were then complexed to iridium(III) giving highly luminescent species. Re-evaluation of these compounds against both cell lines was then undertaken and improved potency (up to 72-fold) was observed, giving IC50 values of 0.36-11 mu M for LNCaP and 0.85-5.9 mu M for PC-3. Preliminary screens for in vivo toxicity were conducted using a zebrafish model showing a wide range of induced toxicity depending of the compound evaluated. Apoptosis and Caspase-3 levels were also determined and showed no statistical difference between some of the treated specimens and the controls. This study may identify novel therapeutic agents for advanced stage of prostate cancer in humans. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.035

文献信息

• Triazole Inhibitors of <i>Cryptosporidium parvum</i> Inosine 5′-Monophosphate Dehydrogenase
  作者：Sushil K. Maurya、Deviprasad R. Gollapalli、Shivapriya Kirubakaran、Minjia Zhang、Corey R. Johnson、Nicole N. Benjamin、Lizbeth Hedstrom、Gregory D. Cuny

  DOI：10.1021/jm900410u

  日期：2009.8.13

  Cryptosporidium parvum is an important human pathogen and potential bioterrorism agent. This protozoan parasite cannot salvage guanine or guanosine and therefore relies on inosine 5′-monophosphate dehydrogenase (IMPDH) for biosynthesis of guanine nucleotides and hence for survival. Because C. parvum IMPDH is highly divergent from the host counterpart, selective inhibitors could potentially be used

  Cryptosporidium parvum是一种重要的人类病原体和潜在的生物恐怖主义剂。这种原生动物寄生虫不能挽救鸟嘌呤或鸟苷，因此依赖肌苷 5'-单磷酸脱氢酶 (IMPDH) 进行鸟嘌呤核苷酸的生物合成，从而生存。由于C. parvum IMPDH 与宿主对应物高度不同，选择性抑制剂可能用于治疗隐孢子虫病，对其哺乳动物宿主的影响最小。描述了一系列含 1,2,3-三唑的醚Cp IMPDH 抑制剂。构效关系研究表明，需要在醚的 α-位上有一个小的烷基，( R )-对映异构体的活性明显高于 ( S)-对映异构体。悬垂苯环的 3- 和/或 4- 位的吸电子基团是最好的，并且在存在和不存在牛血清白蛋白的情况下，含喹啉的抑制剂向​​喹啉-N-氧化物的转化均保持抑制活性。1,2,3-三唑Cp IMPDH 抑制剂为阐明 IMPDH 在C. parvum 中的作用提供了新工具，并可作为治疗隐孢子虫病的潜在疗法。
• A comparison of novel organoiridium(III) complexes and their ligands as a potential treatment for prostate cancer
  作者：Samantha C. Hockey、Gregory J. Barbante、Paul S. Francis、Jarrad M. Altimari、Prusothman Yoganantharajah、Yann Gibert、Luke C. Henderson

  DOI：10.1016/j.ejmech.2015.12.035

  日期：2016.2

  A range of 1,4-substituted 2-pyridyl-N-phenyl triazoles were synthesised and evaluated for their anti proliferative properties against lymph node cancer of the prostate (LNCaP) and bone metastasis of prostate cancer (PC-3) cells. Excellent-to-low IC50 values were determined (5.6-250 mu M), and a representative group of 4 ligands were then complexed to iridium(III) giving highly luminescent species. Re-evaluation of these compounds against both cell lines was then undertaken and improved potency (up to 72-fold) was observed, giving IC50 values of 0.36-11 mu M for LNCaP and 0.85-5.9 mu M for PC-3. Preliminary screens for in vivo toxicity were conducted using a zebrafish model showing a wide range of induced toxicity depending of the compound evaluated. Apoptosis and Caspase-3 levels were also determined and showed no statistical difference between some of the treated specimens and the controls. This study may identify novel therapeutic agents for advanced stage of prostate cancer in humans. (C) 2015 Elsevier Masson SAS. All rights reserved.