thioacetic acid S-[2-(3-nitrophenyl)ethyl] ester | 402508-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: thioacetic acid S-[2-(3-nitrophenyl)ethyl] ester
• 英文别名: S-[2-(3-nitrophenyl)ethyl] ethanethioate
• CAS: 402508-77-4
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: SXBQZQUYIIJFFB-UHFFFAOYSA-N

物化性质

• 沸点：
  366.0±25.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-[2-(3-nitrophenyl)ethyl] ester 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 以97%的产率得到2-(3-nitrophenyl)ethanesulfonic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500
• 作为产物：
  描述：

  3-硝基苯乙醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 80.0h， 生成 thioacetic acid S-[2-(3-nitrophenyl)ethyl] ester
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500

文献信息

• Controlling the Structure, Properties and Surface Reactivity of Clickable Azide‐Functionalized Au ₂₅ (SR) ₁₈ Nanocluster Platforms Through Regioisomeric Ligand Modifications
  作者：Praveen N. Gunawardene、Julia Martin、Jonathan M. Wong、Zhifeng Ding、John F. Corrigan、Mark S. Workentin

  DOI：10.1002/anie.202205194

  日期：2022.7.18

  The correlational properties of regioisomeric, azide-functionalized Au25(SR)18 nanoclusters have been explored, and the molecular structures of the neutral forms of these clusters have been obtained. Although the optical properties are similar, alterations to electrochemical profiles and cluster–surface reactivity with a strained-alkyne have been observed that appear to change as the position of the

  研究了区域异构、叠氮化物功能化的Au 25 (SR) 18纳米团簇的相关性质，并获得了这些团簇的中性形式的分子结构。尽管光学性质相似，但已观察到电化学曲线和与应变炔烃的簇表面反应性的变化，这些变化似乎随着表面叠氮基部分位置的变化而变化。