N-(2-(5-(furan-2-yl)-1H-pyrazol-3-yl)phenyl)methanesulfonamide | 1548752-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-(5-(furan-2-yl)-1H-pyrazol-3-yl)phenyl)methanesulfonamide
• 英文别名: N-[2-[5-(furan-2-yl)-1H-pyrazol-3-yl]phenyl]methanesulfonamide
• CAS: 1548752-97-1
• 化学式: C₁₄H₁₃N₃O₃S
• 分子量: 303.342
• InChiKey: WTZMVLGEAARCSN-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 一水合肼 作用下， 以 乙腈 为溶剂， 生成 N-(2-(5-(furan-2-yl)-1H-pyrazol-3-yl)phenyl)methanesulfonamide
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

  DOI：

  10.1021/acschembio.5b00934

文献信息

• METHODS FOR USE OF SMALL MOLECULE ACTIVATORS OF HEM-Y / PROTOPORPHYRINOGEN OXIDASE (PPO)
  申请人：Vanderbilt University

  公开号：US20160213780A1

  公开（公告）日：2016-07-28

  A method for treating a microbial infection involves administering an effective amount of a compound of the formula: wherein R 1 is H, alkyl, aryl, heteroaryl, R 2 is H, halogen, alkyl, aryl, heteroaryl, R 3 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 4 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 5 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 6 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 7 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 8 is —CR 3 , O, S, wherein R 5 and R 6 , R 7 and R 6 , R 5 and R 4 , R 4 and R 3 can cyclize forming a 3-10 member ring comprising C, O, S, and/or N optionally substituted with one or more R 3 ; and administering light therapy, such as a photodynamic therapy (PDT) light source.

  一种治疗微生物感染的方法包括给予一定量的化合物，其化学式为：其中R1为H，烷基，芳基，杂环芳基，R2为H，卤素，烷基，芳基，杂环芳基，R3为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R4为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R5为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R6为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R7为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R8为—CR3，O，S，其中R5和R6，R7和R6，R5和R4，R4和R3可以环化形成一个由C，O，S和/或N组成的3-10成员环，可选地取代一个或多个R3；并且给予光疗法，例如光动力疗法（PDT）光源。
• COMPOSITIONS AND METHODS FOR TREATING MICROBIAL INFECTIONS
  申请人：Vanderbilt University

  公开号：US20150174130A1

  公开（公告）日：2015-06-25

  Embodiments of the presently-disclosed subject matter include activators of HssRS that induce endogenous heme biosynthesis by perturbing central metabolism. These molecules are toxic to fermenting S. aureus , including clinically relevant small colony variants (SCVs). The utility of targeting fermenting bacteria is exemplified by the fact that this compound prevents the emergence of antibiotic resistance, enhances phagocyte killing, and reduces S. aureus pathogenesis. This small molecule is a powerful tool not only for studying bacterial heme biosynthesis and central metabolism, but also establishes targeting of fermentation as a viable antibacterial strategy.
• US9867879B2
  申请人：——

  公开号：US9867879B2

  公开（公告）日：2018-01-16