N,4-二苯基哌嗪-1-甲酰胺 | 4791-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: N,4-二苯基哌嗪-1-甲酰胺
• 英文名称: N,4-diphenylpiperazine-1-carboxamide
• 英文别名: 4-phenyl-piperazine-1-carboxylic acid anilide
• CAS: 4791-20-2
• 化学式: C₁₇H₁₉N₃O
• mdl: MFCD01358911
• 分子量: 281.357
• InChiKey: SAKOVSGMQXGABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  N,4-二苯基哌嗪-1-甲酰胺 在 C₃₀H₂₉BrMnNO₂P₂ 、 potassium tert-butylate 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 16.0h， 以83%的产率得到苯胺
  参考文献：
  名称：

  通过酰胺、氨基甲酸酯、尿素衍生物和聚氨酯的锰催化转移氢化间接减少二氧化碳并回收聚合物

  摘要：

  极性键（特别是羰基）的减少在有机化学和生物学中具有根本重要性。在此，我们报道了一种锰钳配合物作为一种多功能催化剂，用于酰胺、氨基甲酸酯、尿素衍生物甚至聚氨酯的转移氢化，产生相应的醇、胺和甲醇产品。由于这些化合物类别可以使用CO 2作为C1 结构单元来制备，因此所报道的反应代表了一种间接还原CO 2的方法。值得注意的是，这些是通过转移氢化还原氨基甲酸酯和脲衍生物以及酰胺中 C-N 键断裂的第一个例子。成功还原 12 种尿素衍生物、26 种氨基甲酸酯和 11 种酰胺，凸显了该方法的普遍适用性。相应的胺、醇和甲醇的产率达到97%，收率良好。此外，聚氨酯已成功转化，这代表了实现循环经济的可行战略。基于控制实验和观察到的中间体，提出了可行的机制。

  DOI：

  10.1039/d1sc02663a
• 作为产物：
  描述：

  N-苯基哌嗪 、 异氰酸苯酯 在 4-carboxyphenylsulfonamid resin 、 N,N-二异丙基乙胺 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N,4-二苯基哌嗪-1-甲酰胺
  参考文献：
  名称：

  Solid-phase synthesis of unsymmetrical ureas through the use of Kenner safety-catch linker

  摘要：

  A new strategy for the solid-phase synthesis of unsymmetrical ureas is described. Upon treatment of Kenner safety-catch linker with an isocyanate, followed by TMSCHN2 or iodoacetonitrile and an amine, the corresponding unsymmetrical ureas are released in solution. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02656-4

文献信息

• Use of capsaicin receptor antagonists to treat symptoms of tear gas exposure
  申请人：Bakthavatchalam Rajagopal

  公开号：US20090082362A1

  公开（公告）日：2009-03-26

  Disclosed are diaryl piperazines and related compounds. These compounds are selective modulators of capsaicin receptors, including human capsaicin receptors, that are, therefore, useful in the treatment of a chronic and acute pain conditions, itch and urinary incontinence. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also provided. Compounds of the invention are also useful as probes for the localization of capsaicin receptors and as standards in assays for capsaicin receptor binding and capsaicin receptor mediated cation conductance. Methods of using the compounds in receptor localization studies are given.

  本发明涉及二芳基哌嗪和相关化合物。这些化合物是辣椒素受体的选择性调节剂，包括人类辣椒素受体，因此在治疗慢性和急性疼痛、瘙痒和尿失禁等疾病方面非常有用。本发明还提供了治疗这些疾病的方法以及药物组合物的包装。本发明的化合物还可用作辣椒素受体定位的探针和辣椒素受体结合和辣椒素受体介导的阳离子传导的测定标准。给出了使用这些化合物进行受体定位研究的方法。
• Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma
  作者：Justin Anglin、Reza Beheshti Zavareh、Philipp N. Sander、Daniel Haldar、Edouard Mullarky、Lewis C. Cantley、Alec C. Kimmelman、Costas A. Lyssiotis、Luke L. Lairson

  DOI：10.1016/j.bmcl.2018.04.061

  日期：2018.9

  Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease. To this end, from a high throughput screen of similar to 800,000 molecules, 4-(1H-indol-4-yl)-N-phenylpiperazine-1-carboxamide was identified as an inhibitor of GOT1. Mouse pharmacokinetic studies revealed that potency, rather than inherent metabolic instability, would limit immediate cell- and rodent xenograft-based experiments aimed at validating this potential cancer metabolism-related target. Medicinal chemistry-based optimization resulted in the identification of multiple derivatives with >10-fold improvements in potency, as well as the identification of a tryptamine-based series of GOT1 inhibitors. (C) 2018 Elsevier Ltd. All rights reserved.
• Antidepressant activity of carbamates and urea derivatives
  作者：Shahnaz Perveen、Nasreen Fatima、Muhammad Aitmaud Khan、Ahsana Dar、Khalid M. Khan、Nighat Afza、Wolfgang Voelter

  DOI：10.1007/s00044-011-9797-8

  日期：2012.9

  Thirteen (13) compounds of N-phenyl-O-alkyl carbamates (1 and 3), N,N-diethyl-N'-alkyl/aryl/phenylpiperazinoureas (4-6, 8-12), N-phenyl-N'-phenylpiperazino/imidazoureas (2, 7), and N-ethyl-(N'-phenylpiperazino) thioureas 13 were synthesized and tested for their antidepressant-like activity in mice. It was found that compound N-phenyl-O-heptyl carbamate 1 and N-phenyl-N'-phenylpiperazinourea 2 showed 32.5 and 27.7% antidepressant activity in the forced swim test in mice, respectively. Considering other carbamates it was found that a decrease in alkyl chain length caused a marked decline in the antidepressant activity. Compounds 1-4 show even higher activities in the forced swim test than the standard phenelzine.
• MODULATORS OF VASOPRESSIN RECEPTORS WITH THERAPEUTIC POTENTIAL
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20150376198A1

  公开（公告）日：2015-12-31

  Compounds comprising piperazines, piperidines, spiro-furanopiperidines, and analogs thereof are provided that are modulators, such as positive allosteric modulators, of one or more subclasses of vasopressin receptors. The compounds can be selective modulators of one or more subclasses of vasopressin receptors. Compounds of the invention can be used in the treatment of a condition wherein modulating a vasopressin receptor is medically indicated for treatment of the condition.
• Indirect reduction of CO₂ and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes
  作者：Xin Liu、Thomas Werner

  DOI：10.1039/d1sc02663a

  日期：——

  approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C–N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained

  极性键（特别是羰基）的减少在有机化学和生物学中具有根本重要性。在此，我们报道了一种锰钳配合物作为一种多功能催化剂，用于酰胺、氨基甲酸酯、尿素衍生物甚至聚氨酯的转移氢化，产生相应的醇、胺和甲醇产品。由于这些化合物类别可以使用CO 2作为C1 结构单元来制备，因此所报道的反应代表了一种间接还原CO 2的方法。值得注意的是，这些是通过转移氢化还原氨基甲酸酯和脲衍生物以及酰胺中 C-N 键断裂的第一个例子。成功还原 12 种尿素衍生物、26 种氨基甲酸酯和 11 种酰胺，凸显了该方法的普遍适用性。相应的胺、醇和甲醇的产率达到97%，收率良好。此外，聚氨酯已成功转化，这代表了实现循环经济的可行战略。基于控制实验和观察到的中间体，提出了可行的机制。