2-(4-methoxyphenyl)-N-phenyldiazenecarboxamide | 35524-37-9

• 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: 2-(4-methoxyphenyl)-N-phenyldiazenecarboxamide
• 英文别名: (1E)-1-(4-methoxyphenyl)imino-3-phenyl-urea；1-(4-methoxyphenyl)imino-3-phenylurea
• CAS: 35524-37-9
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: JCUOXIXNGSLDHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 2-(4-methoxyphenyl)-N-phenyldiazenecarboxamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  铱偶氮甲酰胺配合物：可变配位模式、C-H 活化、转移氢化催化和机理洞察

  摘要：

  偶氮甲酰胺是一类特殊的偶氮配体，由于其多功能的结合模式和配位灵活性，显示出有趣的电子特性。这些特性可能对它们在均相催化中的应用具有重要意义。在本报告中，介绍了两种不同的偶氮甲酰胺配体的半夹心 Ir-Cp* 复合物。使用碱和氯化物提取配体实现了配体的不同配位基序，以得到 N ∧ N-、N ∧ O- 和 N ∧ C-螯合的单体铱配合物。对于配体azocarboxamide具有甲氧基取代的苯环，N的混合物∧ C-螯合单核（铱5）和N ∧ N，N- ∧C-螯合双核配合物（Ir-4）是通过激活芳环的C-H键获得的。对于没有甲氧基取代基的配体，没有观察到这种 C-H 活化。通过光谱分析证实了复合物的分子身份，而 X 射线衍射分析进一步证实了复合物的三足钢琴凳结构以及上述结合模式。发现所有配合物作为在碱存在下羰基转移氢化的预催化剂都表现出显着的活性，即使在低催化剂负载下也是如此。反应条件的优化揭示了Ir

  DOI：

  10.1021/acs.organomet.1c00468
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-4-phenylsemicarbazide 在 ammonium cerium (IV) nitrate 作用下， 以 甲醇 为溶剂， 以98%的产率得到2-(4-methoxyphenyl)-N-phenyldiazenecarboxamide
  参考文献：
  名称：

  Biological evaluation of diazene derivatives as anti-tubercular compounds

  摘要：

  Despite efforts made in chemotherapeutic research in the past and present, Mycobacterium tuberculosis (M.tb), the etiological agent of tuberculosis, still causes more than a million deadly casualties each year, second only to HIV. The rapid generation and spread of drug resistant strains, a problem exacerbated by co-infection with HIV demands further efforts in the investigation of novel classes of anti-tubercular compounds. A library of eight substituted diazenecarboxamides, three carbamoyldiazenecarboxylates and four diazene-1,2-dicarboxamides was synthesized in a straightforward manner followed by a biological evaluation of the compounds. We observed minimal inhibitory concentrations below 10 mu g/mL against the H37Rv lab strain of M.tb. Three compounds that showed a potency of 90% growth inhibition of M.tb at a concentration lower than 10 mu g/mL were further evaluated and showed potency against other clinically relevant mycobacterial species such as Mycobacterium bovis, Mycobacterium avium and Mycobacterium ulcerans. The selected compounds were examined for acute cell toxicity on a murine macrophage like monocyte cell line J774 A.1 in which the cell viability was reduced by 50% at concentrations ranging from 7.4 mu g/mL to 20.7 mu g/mL. Neither of the three compounds showed signs of genotoxicity by VITOTOX or by Comet assay. The study was complemented by demonstration of the inhibition of intracellular replication of M.tb H37Rv inside J774 A.1 cells at 2 mu g/mL concentration and the susceptibility of a MDR LAM-1 strain at concentrations between 5 and 1 mu g/mL of the most active compound. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.057