4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl)benzenamine | 71422-89-4

• 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: 4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl)benzenamine
• 英文别名: 1-[(p-aminophenyl)sulfonyl]-4-(p-fluorophenyl)piperazine；4-[4-(4-fluorophenyl)piperazin-1-yl]sulfonylaniline
• CAS: 71422-89-4
• 化学式: C₁₆H₁₈FN₃O₂S
• 分子量: 335.402
• InChiKey: BZISLBGNSPAWFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl)benzenamine 、 norcantharidin 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以70%的产率得到N-(4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl)phenyl)-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboximide
  参考文献：
  名称：

  Synthesis and biological evaluation of norcantharidin derivatives as protein phosphatase-1 inhibitors

  摘要：

  Cantharidin and norcantharidin display anticancer activity against a broad range of tumor cell lines. In this study, we have synthesized a series of norcantharidin derivatives and evaluated their cytotoxic effects on four human tumor cell lines together with the genetically normal human diploid fibroblast line WI-38. One of our compounds (1S,4R)-3-((4-(4-(4-fluorophenyl) piperazin-1-ylsulfonyl) phenyl) carbamoyl)-7-oxa-bicyclo[2.2.1] heptane-2-carboxylic acid (12) exhibited potent cytotoxic effects on the tumor cell lines A-549, HepG2, HeLa, and HCT-8, whereas it was less toxic to WI-38 cells than its parent compound, norcantharidin. In addition, this compound inhibited protein phosphatase-1 activity and microtubule formation in HeLa cells, and it also interacts with calf thymus DNA. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.032
• 作为产物：
  描述：

  1-(4-Fluorophenyl)-4-[(4-nitrophenyl)sulfonyl]piperazine 在 氧化铂 氢气 、 碳 、 二氯甲烷 、 Sodium sulfate-III 、 甲醇 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以to give 2.16 g of 1-[(p-aminophenyl)sulfonyl]-4-(p-fluorophenyl)piperazine containing a minor impurity的产率得到4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl)benzenamine
  参考文献：
  名称：

  Antihypertensive 4-aminoquinolines

  摘要：

  用于治疗高血压哺乳动物，包括人类的抗高血压化合物，其化学式为III：##STR1## 其中X为氯或三氟甲基；其中R为诸如三嗪基、吡嗪基、吡啶基、嘧啶基、苯基或上述基团中被一个或两个三氟甲基、卤、烷基、烷氧基、双烷基氨基或烷基硫基基团取代的基团；或R为以下基团##STR2## 其中R.sub.1为苯基、被一个或两个卤原子、烷氧基或烷基取代的苯基、三氟甲基，或R.sub.1为烷基苯基磺酰基；或R为--SO.sub.2R.sub.2基团，其中R.sub.2为双烷基氨基、苯基、被卤原子、烷基或烷氧基取代的苯基，或三氟甲基。这些化合物是从（7-氯）-或（7-三氟甲基）-4-氯喹啉或1-[[4-[[(7-氯）-或（7-三氟甲基）喹啉基]氨基]苯基]磺酰基]哌嗪制备的。

  公开号：

  US04159331A1

文献信息

• Exploration and structure–activity relationship research of benzenesulfonamide derivatives as potent TRPV4 inhibitors for treating acute lung injury
  作者：Mengyuan Wang、Yuehao Zhang、Xu Cai、Shangze Yang、Shiyang Sun、Sheng Zhou、Weizhen Lv、Na Du、Yan Li、Chao Ma、Kexin Ren、Mingliang Liu、Bowen Tang、Apeng Wang、Xingjuan Chen、Pengyun Li、Kai Lv、Zhibing Zheng

  DOI：10.1016/j.bioorg.2024.107396

  日期：2024.6

  RN-9893 in TRPV4 current inhibition rates (87.6 % and 83.2 % at 10 μM, against RN-9893′s 49.4 %). For the first time, these RN-9893 analogues were profiled in an mouse model, where intraperitoneal injections of or at 10 mg/kg notably mitigated symptoms of acute lung injury induced by lipopolysaccharide (LPS). These outcomes indicate that compounds and are promising candidates for acute lung injury treatment

  RN-9893 是 Renovis Inc. 鉴定的一种 TRPV4 拮抗剂，表现出对 TRPV4 通道的显着抑制作用。这项研究涉及合成和评估三个系列的 RN-9893 类似物的 TRPV4 抑制功效。值得注意的是，与 RN-9893 (IC = 2.07 ± 0.90 μM) 相比，化合物和对 TRPV4 的抑制效力增加了 2.9 至 4.5 倍 (IC = 0.71 ± 0.21 μM 和 0.46 ± 0.08 μM)。两种化合物的 TRPV4 当前抑制率也显着优于 RN-9893（10 μM 时为 87.6 % 和 83.2 %，而 RN-9893 为 49.4 %）。首次在小鼠模型中对这些 RN-9893 类似物进行了分析，腹腔注射 10 mg/kg 或 10 mg/kg 可显着减轻脂多糖 (LPS) 诱导的急性肺损伤症状。这些结果表明化合物和化合物是治疗急性肺损伤的有希望的候选者。
• Synthesis and evaluation of the cell cycle arrest and CT DNA interaction properties of 4β-amino-4′-O-demethyl-4-deoxypodophyllotoxins
  作者：Jian-Fei Liu、Chun-Yan Sang、Wen-Wen Qin、Jie Zhao、Lin Hui、Yi-Lan Ding、Shi-Wu Chen

  DOI：10.1016/j.bmc.2013.09.026

  日期：2013.11

  A series of 4 beta-amino-4'-O-demethyl-4-deoxypodophyllotoxin derivatives were synthesized, and their cytotoxicities against several human cancer cell lines, including HepG2, A549, HeLa and HCT-8 cells, evaluated. Some of these compounds exhibited higher levels of cytotoxicity than the anticancer drug etoposide. 4 beta-N-(4-Nitrophenyl piperazinyl)-4'-O-demethyl-4-deoxypodophyllotoxin (11) was found to be the most potent synthesized compound in the current study, and induced cell cycle arrest in the G2/M phase in HeLa cells, which was accompanied by apoptosis. Furthermore, this compound activated the expression of cdc2, cyclin B1, p53 and caspase-3 in HeLa cells, leading to changes in the conformation of calf thymus DNA from the B-form to a more compact C-form. (C) 2013 Elsevier Ltd. All rights reserved.
• US4159331A
  申请人：——

  公开号：US4159331A

  公开（公告）日：1979-06-26