4-(4'-sulphanilyl)-1-phenylpiperazine | 150558-10-4

• 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'-sulphanilyl)-1-phenylpiperazine
• 英文别名: 1-phenyl-4-sulfanilyl-piperazine；1-Phenyl-4-sulfanilyl-piperazin；1-(4-aminophenylsulfonyl)-4-phenylpiperazine；Piperazine, 1-[(4-aminophenyl)sulfonyl]-4-phenyl-；4-(4-phenylpiperazin-1-yl)sulfonylaniline
• CAS: 150558-10-4
• 化学式: C₁₆H₁₉N₃O₂S
• 分子量: 317.412
• InChiKey: LJNHEZGUNDGDNF-UHFFFAOYSA-N

物化性质

• 沸点：
  529.1±60.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 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：
  5

反应信息

• 作为反应物：
  描述：

  4-(4'-sulphanilyl)-1-phenylpiperazine 在 哌啶 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.0h， 生成 2-(4-Methoxy-phenyl)-3-[4-(4-phenyl-piperazine-1-sulfonyl)-phenyl]-thiazolidin-4-one
  参考文献：
  名称：

  新型磺胺类药物的合成及其抗菌功效评价

  摘要：

  4-(4'-磺胺基)-1-苯基哌嗪 (2) 已通过 N-乙酰磺胺基氯 (ASC) 与 1-苯基哌嗪反应，然后用 HCl 乙醇水解产物来制备。水解产物与芳香醛轻松缩合反应生成席夫碱/苯胺/偶氮甲碱 (3a-h)。这些苯胺与氯乙酰氯和硫代乙醇酸（巯基乙酸）发生环缩缩合反应，分别生成 2-氮杂环丁酮和 4-噻唑烷酮。制备的化合物的生物筛选已经在一些细菌菌株上进行了筛选。

  DOI：

  10.1080/10426500490459704
• 作为产物：
  描述：

  1-[(4-nitrobenzene)sulfonyl]-4-phenylpiperazine 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 4-(4'-sulphanilyl)-1-phenylpiperazine
  参考文献：
  名称：

  Discovery and Structure–Activity Relationship of Potent and Selective Covalent Inhibitors of Transglutaminase 2 for Huntington’s Disease

  摘要：

  Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.

  DOI：

  10.1021/jm201310y

文献信息

• Antiviral agent
  申请人：SANWA KAGAKU KENKYUSHO CO., LTD.

  公开号：EP0548798A1

  公开（公告）日：1993-06-30

  An antiviral agent containing a compound represented by formula (I): wherein R₁ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group; R₂, R₃, and R₄, which may be the same or different, each represent a hydrogen atom, an amino group, a substituted or unsubstituted alkylamino group, an acylamino group, a substituted or unsubstituted alkyl group, a hydroxyl group, a substituted or unsubstituted alkyloxy group, a halogen atom, a carboxyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted carbamoyl group, a nitro group, a cyano group, a thiol group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group; A represents a nitrogen group or a methylene group; m represents 0 or a natural number; and n represents a natural number, or a pharmaceutically acceptable salt thereof, are disclosed.

  一种抗病毒剂，含有以下式（I）表示的化合物：其中R₁代表取代或未取代的烷基基团，取代或未取代的酰基团，取代或未取代的芳基磺酰基团，取代或未取代的烷基磺酰基团，取代或未取代的苯基，或取代或未取代的杂环基团；R₂、R₃和R₄，可以相同也可以不同，每个代表氢原子，氨基，取代或未取代的烷基氨基基团，酰胺基团，取代或未取代的烷基基团，羟基，取代或未取代的烷氧基团，卤素原子，羧基，取代或未取代的烷基羰基基团，取代或未取代的烷氧羰基基团，取代或未取代的芳基氧羰基基团，取代或未取代的氨基甲酰基团，硝基基团，氰基团，硫基团，取代或未取代的烷硫基团，取代或未取代的苯基，或取代或未取代的杂环基团；A代表氮基团或亚甲基团；m表示0或自然数；n表示自然数，或其药学上可接受的盐。
• 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：2024.4

  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。
• Kohlbach, 1937, vol. 11, p. 99,116
  作者：Kohlbach

  DOI：——

  日期：——
• Discovery and Structure–Activity Relationship of Potent and Selective Covalent Inhibitors of Transglutaminase 2 for Huntington’s Disease
  作者：Michael E. Prime、Ole A. Andersen、John J. Barker、Mark A. Brooks、Robert K. Y. Cheng、Ian Toogood-Johnson、Stephen M. Courtney、Frederick A. Brookfield、Christopher J. Yarnold、Richard W. Marston、Peter D. Johnson、Siw F. Johnsen、Jordan J. Palfrey、Darshan Vaidya、Sayeh Erfan、Osamu Ichihara、Brunella Felicetti、Shilpa Palan、Anna Pedret-Dunn、Sabine Schaertl、Ina Sternberger、Andreas Ebneth、Andreas Scheel、Dirk Winkler、Leticia Toledo-Sherman、Maria Beconi、Douglas Macdonald、Ignacio Muñoz-Sanjuan、Celia Dominguez、John Wityak

  DOI：10.1021/jm201310y

  日期：2012.2.9

  Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.
• SYNTHESIS OF NOVEL SULPHONAMIDES AND EVALUATION OF THEIR ANTIBACTERIAL EFFICACY
  作者：H. S. Patel、H. J. Mistry

  DOI：10.1080/10426500490459704

  日期：2004.6

  4-(4′-sulphanilyl)-1-phenyl pipearzine (2) has been prepared by ther reaction of N-acetyl sulphanilyl chloride (ASC) with 1-phenyl piperazine followed by the hydrolysis of the product by ethanolic HCl. The hydrolyze product on facile condensation reaction with aromatic aldehydes yields Schiff bases/anils/azomethines (3a–h). These anils on cyclo condensation reaction with chloro acetyl chloride and

  4-(4'-磺胺基)-1-苯基哌嗪 (2) 已通过 N-乙酰磺胺基氯 (ASC) 与 1-苯基哌嗪反应，然后用 HCl 乙醇水解产物来制备。水解产物与芳香醛轻松缩合反应生成席夫碱/苯胺/偶氮甲碱 (3a-h)。这些苯胺与氯乙酰氯和硫代乙醇酸（巯基乙酸）发生环缩缩合反应，分别生成 2-氮杂环丁酮和 4-噻唑烷酮。制备的化合物的生物筛选已经在一些细菌菌株上进行了筛选。