1-(萘-2-磺酰基)-哌嗪 | 179051-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(萘-2-磺酰基)-哌嗪
• 英文名称: 1-(naphthalen-2-ylsulfonyl)piperazine
• 英文别名: 1-(2-naphthalenesulfonyl)piperazine；1-(2-naphthylsulphonyl)piperazine；N-(2-napthylsulfonyl)piperazine；N-(2-naphthylsulfonyl)piperazine；1-(Naphthalene-2-sulfonyl)-piperazine；1-naphthalen-2-ylsulfonylpiperazine
• CAS: 179051-76-4
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: OJWPAXRMRPPQBG-UHFFFAOYSA-N

物化性质

• 沸点：
  471.7±55.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)
• 溶解度：
  32.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-(萘-2-磺酰基)-哌嗪 在 N-甲基吗啉 、 吡啶 、 TEA 、 硫化氢 、 ammonium acetate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 92.0h， 生成 3-{2-(Naphthalene-2-sulfonylamino)-3-[4-(naphthalene-2-sulfonyl)-piperazin-1-yl]-3-oxo-propyl}-benzamidine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potent Thrombin Inhibitors:  Piperazides of 3-Amidinophenylalanine

  摘要：

  Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N-alpha-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.

  DOI：

  10.1021/jm960668h
• 作为产物：
  描述：

  tert-butyl 4-(naphthalene-2-ylsulfonyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 1-(萘-2-磺酰基)-哌嗪
  参考文献：
  名称：

  Inhibitors of histone deacetylase

  摘要：

  揭示了抑制组蛋白去乙酰化酶（HDAC）酶活性的化合物。还揭示了包含这些化合物的药物组合物，以及治疗病症的方法，特别是至少部分由HDAC介导的增殖性病症。

  公开号：

  US20050234033A1

文献信息

• Sulfonamide derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06359134B1

  公开（公告）日：2002-03-19

  The present invention provides compounds which specifically inhibit FXa, which are effective when orally administered and which are useful as a safe medicine for the prevention or treatment of diseases caused by thrombus or infarction. Compounds of this invention are piperazinones of the formula: wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; the ring A is an optionally substituted divalent nitrogen-containing heterocyclic group, in addition to being substituted by the group of the formula: and the group of the formula: Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent heterocyclic group; X is a direct bond or an optionally substituted alkylene chain; Z is (1) an amino group substituted with an optionally substituted hydrocarbon group, (2) an optionally substituted imino group or (3) an optionally substituted nitrogen-containing heterocyclic group; provided that when X is a direct bond and Z is an optionally substituted 6-membered nitrogen-containing aromatic heterocyclic group, Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent unsaturated heterocyclic group; or a salt thereof.

  本发明提供了一种化合物，该化合物特异性地抑制FXa，口服给药有效，并且用作预防或治疗由血栓或梗死引起的疾病的药物是安全的。本发明的化合物是哌嗪酮的公式： 其中R1是可选地取代的烃基或可选地取代的杂环基；环A是除了被公式：的基团取代的之外的可选地取代的二价含氮杂环基： 和公式的基团： Y是可选地取代的二价烃基或可选地取代的二价杂环基；X是直接键或可选地取代的亚烷基链；Z是（1）与可选地取代的烃基取代的氨基，（2）可选地取代的亚氨基或（3）可选地取代的含氮杂环基；当X是直接键并且Z是可选地取代的6-成员含氮芳香杂环基时，Y是可选地取代的二价烃基或可选地取代的二价不饱和杂环基；或其盐。
• Inhibitors of histone deacetylase
  申请人：Anandan K. Sampath

  公开号：US20050250784A1

  公开（公告）日：2005-11-10

  Disclosed are compounds which inhibit histone deacetylase (HDAC) enzymatic activity. Also disclosed are pharmaceutical compositions comprising such compounds as well as methods to treat conditions, particularly proliferative conditions, mediated at least in part by HDAC.

  揭示了抑制组蛋白去乙酰化酶（HDAC）酶活性的化合物。还揭示了包含这些化合物的药物组合物，以及治疗由HDAC至少部分介导的疾病的方法，特别是增殖性疾病。
• Diphenyl triazine hybrids inhibit α-synuclein fibrillogenesis: Design, synthesis and in vitro efficacy studies
  作者：Mudasir Maqbool、Joshna Gadhavi、Pravin Hivare、Sharad Gupta、Nasimul Hoda

  DOI：10.1016/j.ejmech.2020.112705

  日期：2020.12

  hypotheses for Parkinson’s disease (PD), therefore, its inhibition and disaggregation is an optimistic approach for the treatment of PD. Here, we report design, synthesis and in-vitro efficacy studies of a series of diphenyl triazine hybrids as potential inhibitors of α-syn fibrillogenesis. From the docking studies, we concluded that compounds A1, A2, A4, A8 and A9 display promising binding affinity with the

  α-突触核蛋白（α-syn）的聚集是帕金森氏病（PD）的主要假设之一，因此，其抑制和分解是治疗PD的一种乐观方法。在这里，我们报告一系列二苯基三嗪杂种作为α-syn原纤维形成的潜在抑制剂的设计，合成和体外功效研究。从对接研究中，我们得出结论，化合物A1，A2，A4，A8和A9与具有-6.0，-7.0，-6.3，-6.6和-6.7 Kcal结合能的α-syn必需残基显示出有希望的结合亲和力。 / mol。使用多步有机合成反应合成目标化合物。化合物A1，A2，A4，A8和A9硫黄素-T分析和荧光显微镜观察到α-syn原纤维形成明显减少。另外，这些化合物A1，A2，A4，A8和A9也被证明是预聚集形式的α-syn的良好分解剂。除A2外，大多数化合物对小鼠胚胎成纤维细胞（MEF）和人腺癌肺泡基底上皮细胞（A549）均无细胞毒性。总体而言，可以进一步研究基于二苯三嗪的化合物治疗突触核蛋白病和主要观察到α-syn的路易体痴呆。
• Synthesis and structure-activity relationship study of 8-hydroxyquinoline-derived Mannich bases as anticancer agents
  作者：Arthur Y. Shaw、Chun-Yi Chang、Mei-Yuan Hsu、Pei-Jung Lu、Chia-Ning Yang、Hui-Ling Chen、Cheng-Wei Lo、Chung-Wai Shiau、Ming-Kai Chern

  DOI：10.1016/j.ejmech.2010.03.008

  日期：2010.7

  early study on the structural modifications of clioquinol, more 8-hydroxyquinoline-derived Mannich bases were synthesized and examined for growth-inhibitory effect. Taken Mannich base 1 as our lead compound, upon replacement of either sulfonyl group with methylene group or piperazine ring with ethylenediamine group resulted in an appreciable increase in potency. On the other hand, as 8-hydroxyquinoline

  为了继续我们对氯喹醇的结构修饰的早期研究，合成了更多的8-羟基喹啉衍生的曼尼希碱，并检查了其抑制生长的作用。以曼尼希碱1为先导化合物，用亚甲基取代磺酰基或用乙二胺基取代哌嗪环后，效力显着提高。另一方面，当用酚，3-羟基吡啶和1-萘酚代替8-羟基喹啉时，观察到活性急剧下降，表明8-羟基喹啉是活性的关键支架。对HeLa细胞的进一步3D-QSAR分析表明，空间效应和电子效应均对生长抑制有同等作用。两者合计，从两者获得的结构-活性关系体外数据和CoMFA模型值得进一步研究提供有价值的参考。
• [EN] TG2 INHIBITOR COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBITEURS DE TG2 ET UTILISATIONS DE CES DERNIERS
  申请人：UNIV OTTAWA

  公开号：WO2017179018A1

  公开（公告）日：2017-10-19

  There are provided Tissue Transglutaminase (TG2) inhibitor compounds, and compositions and methods of use thereof for the prevention or treatment of a cancer. Compounds of Formula I, and pharmaceutically acceptable salts thereof, are provided: Formula (I).

  提供了组织转谷氨酰胺酶（TG2）抑制剂化合物，以及其用于预防或治疗癌症的组合物和使用方法。提供了化合物I的公式，以及其药用盐：公式（I）。