3-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-ol | 16155-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-ol
• 英文别名: 4-(4-Nitrophenyl)-1-piperazinepropanol
• CAS: 16155-06-9
• 化学式: C₁₃H₁₉N₃O₃
• 分子量: 265.312
• InChiKey: XNDUOPXMERMAPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.5±45.0 °C(predicted)
• 密度：
  1.227±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-ol 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 生成 3-[4-(4-aminophenyl)-piperazin-1-yl]propan-1-ol
  参考文献：
  名称：

  2-氨基嘧啶衍生物作为 JAK2 和 FLT3 的选择性双重抑制剂治疗急性髓性白血病

  摘要：

  JAK2 和 FLT3 的双重抑制剂可以协同控制急性髓性白血病 (AML) 的发展，并克服与 FLT3 抑制相关的 AML 继发性耐药性。因此，我们设计并合成了一系列 4-哌嗪基-2-氨基嘧啶作为 JAK2 和 FLT3 的双重抑制剂，并提高了它们对 JAK2 的选择性。筛选级联显示化合物11r对 JAK2、FLT3 和 JAK3表现出抑制活性，IC 50值分别为 2.01、0.51 和 104.40 nM。化合物11r以 51.94 的比率实现了对 JAK2 的高选择性，并且还在 HEL (IC 50  = 1.10 μM) 和 MV4-11 (IC 50  = 9.43 nM) 细胞系中显示出有效的抗增殖活性。在一个在体外代谢测定中，11r在人肝微粒体 (HLM) 中表现出中等稳定性，半衰期为 44.4 分钟，在大鼠肝微粒体 (RLM) 中，半衰期为 143 分钟。在药代动力学研究中，化合物11r表现出适度的吸收（Tmax

  DOI：

  10.1016/j.bioorg.2023.106442
• 作为产物：
  描述：

  1-(4-硝基苯基)哌嗪 、 3-溴-1-丙醇 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以54%的产率得到3-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-ol
  参考文献：
  名称：

  Synthesis of a novel series of 4-arylpiperazinyl derivatives linked to a 2-(pyridin-3-yl)-1H-benzimidazole as new Delavirdine analogues

  摘要：

  The synthesis of a series of substituted arylpiperazines linked to a 2-(pyridin-3-yl)-1H-benzo[d]imidazole scaffold through an alkylic linker is reported. The novel 1-(2-(4-arylpiperazin-1-yl)alkyl)-2-(pyridin-3-yl)-1H-benzimidazole derivatives are structurally related to the anti-HIV-1 drug Delavirdine and belong to the bis(heteroaryl)piperazines family (BHAPs), a well known HIV-1 reverse transcriptase inhibitors group.

  DOI：

  10.1590/s0103-50532010000100011

文献信息

• Diaminothiazoles having antiproliferative activity
  申请人：——

  公开号：US20020151554A1

  公开（公告）日：2002-10-17

  Disclosed are novel diaminothiazoles that are selective inhibitors of Cdk4. These compounds and their pharmaceutically acceptable salts and esters are anti-proliferative agents useful in the treatment or control of solid tumors, in particular breast, colon, lung and prostate tumors. Also disclosed are pharmaceutical compositions containing these compounds as well as intermediates useful in the preparation of the compounds.

  揭示了一种新型的二氨基噻唑，它们是Cdk4的选择性抑制剂。这些化合物及其药学上可接受的盐和酯是抗增殖剂，在治疗或控制实体肿瘤，特别是乳腺、结肠、肺和前列腺肿瘤方面非常有用。还公开了含有这些化合物的药物组合物，以及制备这些化合物的中间体。
• Intermediates useful in the preparation of diaminothiazoles
  申请人：——

  公开号：US20040082595A1

  公开（公告）日：2004-04-29

  Disclosed are novel diaminothiazoles that are selective inhibitors of Cdk4. These compounds and their pharmaceutically acceptable salts and esters are anti-proliferative agents useful in the treatment or control of solid tumors, in particular breast, colon, lung and prostate tumors. Also disclosed are pharmaceutical compositions containing these compounds as well as intermediates useful in the preparation of the compounds.

  本发明涉及新型二氨基噻唑，它们是Cdk4的选择性抑制剂。这些化合物及其药学上可接受的盐和酯是抗增殖剂，可用于治疗或控制实体肿瘤，特别是乳腺、结肠、肺和前列腺肿瘤。还公开了包含这些化合物的药物组合物以及用于制备这些化合物的中间体。
• Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
  作者：Thuy Nguyen、Tianming Yang、Mei-Lin Go

  DOI：10.1016/j.bmcl.2014.02.006

  日期：2014.4

  The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl(1)-NH-Aryl(2) scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• DIAMINOTHIAZOLES AND THEIR USE AS INHIBITORS OF CYCLIN-DEPENDENT KINASE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1358169A2

  公开（公告）日：2003-11-05
• US6756374B2
  申请人：——

  公开号：US6756374B2

  公开（公告）日：2004-06-29