3-(4-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide | 632329-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide
• 英文别名: 3-(4-phenyltriazol-1-yl)benzenesulfonamide
• CAS: 632329-80-7
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: XHKOQCNHXYRHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间氨基苯磺酰胺 在 亚硝酸特丁酯 、 copper(ll) sulfate pentahydrate 、 叠氮基三甲基硅烷 、 sodium ascorbate 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 34.0h， 生成 3-(4-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Metallocene-Based Inhibitors of Cancer-Associated Carbonic Anhydrase Enzymes IX and XII

  摘要：

  In this study, 20 metallocene-based compounds comprising extensive structural diversity were synthesized and evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. These compounds proved moderate to good CA inhibitors in vitro, with several compounds displaying selectivity for cancer-associated isozymes CA IX and CA XII compared to off-target CA I and CA II. Compound 6 was the most potent ferrocene-based inhibitor with K(i)s of 5.9 and 6.8 nM at CA IX and XII, respectively. A selection of key drug-like parameters comprising Log P, Log D, solubility, and in vitro metabolic stability and permeability were measured for two of the ferrocene-based compounds, regioisomers 1 and S. Compounds.1 and 5 were found to have characteristics consistent with lipophilic compounds, however, our findings show that the lipophilicity of the ferrocene moiety is not well modeled by replacement with either a naphthyl or a phenyl moiety in software prediction tools.

  DOI：

  10.1021/jm300427m

文献信息

• [EN] SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME<br/>[FR] SULFONYLURÉES ET COMPOSÉS APPARENTÉS ET LEUR UTILISATION
  申请人：UNIV QUEENSLAND

  公开号：WO2017140778A1

  公开（公告）日：2017-08-24

  The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts, solvates and prodrugs thereof: Formula (I) wherein Q is selected from O, S and Se; J is S or Se; W1 and W2, when present, are independently selected from N and C; R1 and R2 are independently selected from the group consisting of hydrogen, C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, cycloalkenyl, amino, amido, alkylthio, acyl, arylalkyl and acylamido, all of which may be optionally substituted; and wherein at least one of W1 and W2 is present and is a nitrogen atom and when R1 and R2 are cyclic then the respective W1 or W2 may form part of the ring structure. The present invention also relates to pharmaceutical compositions including such compounds, to methods of treatment using such compounds, in particular in relation to NLRP3 inflammasome mediated disorders, and to associated diagnostic uses.

  本发明涉及化合物的公式（I），以及其药学上可接受的盐、溶剂化合物和前药：公式（I）其中Q从O、S和Se中选择；J为S或Se；当存在时，W1和W2独立地从N和C中选择；R1和R2独立地从氢、C1-C12烷基、C2-C12烯基、C2-C12炔基、芳基、杂环烷基、杂芳基、环烷基、环烯基、氨基、酰胺基、烷基硫基、酰基、芳基烷基和酰胺基中选择，其中所有这些基团可能是可选地取代的；其中W1和W2中至少有一个存在且为氮原子，当R1和R2为环时，相应的W1或W2可能构成环结构的一部分。本发明还涉及包括这些化合物的药物组合物，使用这些化合物的治疗方法，特别是与NLRP3炎症小体介导的疾病相关的治疗方法，以及相关的诊断用途。
• Copper-catalysed ligation of azides and acetylenes
  申请人：The Scripps Research Institute

  公开号：EP2226316A1

  公开（公告）日：2010-09-08

  The present invention provides a process of catalyzing a click chemistry ligation reaction between a first reactant having a terminal alkyne moiety and second reactant having an azide moiety for forming a product having a triazole moiety, the click chemistry ligation reaction being performed in a solution in contact with metallic copper, said metallic copper contributing directly or indirectly to the catalysis of the click chemistry ligation reaction.

  本发明提供了一种催化具有末端炔基的第一反应物与具有叠氮基的第二反应物之间的点击化学连接反应以形成具有三唑基的产物的工艺，该点击化学连接反应在与金属铜接触的溶液中进行，所述金属铜直接或间接地促进了点击化学连接反应的催化。
• Sulfonylureas and related compounds and use of same
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：US11130731B2

  公开（公告）日：2021-09-28

  The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.

  本发明提供了某些磺酰脲类及相关化合物，它们在抑制 NLRP3 炎性体活化方面具有优势特性并显示出有用的活性。此类化合物可用于治疗多种疾病，在这些疾病中，炎症过程或更具体地说是 NLRP3 炎症体被认为是一个关键因素。
• [EN] SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME<br/>[FR] SULFONYLURÉES, COMPOSÉS APPARENTÉS, ET LEUR UTILISATION
  申请人：UNIV QUEENSLAND

  公开号：WO2016131098A8

  公开（公告）日：2017-03-16
• COPPER-CATALYSED LIGATION OF AZIDES AND ACETYLENES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1507769B2

  公开（公告）日：2017-10-11