N-(4-nitrobenzyl)ethylenesulfonamide | 533938-05-5

• 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: N-(4-nitrobenzyl)ethylenesulfonamide
• 英文别名: Ethenesulfonic acid 4-nitro-benzylamide；N-[(4-nitrophenyl)methyl]ethenesulfonamide
• CAS: 533938-05-5
• 化学式: C₉H₁₀N₂O₄S
• 分子量: 242.255
• InChiKey: HBKSXXXCFJATJR-UHFFFAOYSA-N

物化性质

• 沸点：
  428.6±47.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-赖氨酸 、 N-(4-nitrobenzyl)ethylenesulfonamide 在 乙二胺四乙酸 作用下， 以 phosphate buffer 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  评估乙烯基磺酰胺作为蛋白质修饰中的巯基选择性烷基化试剂。

  摘要：

  描述了几种模型乙烯基磺酰胺的制备。通过模型乙烯基磺酰胺与半胱氨酸或赖氨酸在不同pH值之间的动力学研究，证明了它们对氨基而言对巯基的出色的选择性反应性。

  DOI：

  10.1016/s0960-894x(02)00950-2
• 作为产物：
  描述：

  2-氯乙烷磺酰氯 、 4-硝基苄胺 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以47%的产率得到N-(4-nitrobenzyl)ethylenesulfonamide
  参考文献：
  名称：

  评估乙烯基磺酰胺作为蛋白质修饰中的巯基选择性烷基化试剂。

  摘要：

  描述了几种模型乙烯基磺酰胺的制备。通过模型乙烯基磺酰胺与半胱氨酸或赖氨酸在不同pH值之间的动力学研究，证明了它们对氨基而言对巯基的出色的选择性反应性。

  DOI：

  10.1016/s0960-894x(02)00950-2

文献信息

• Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the <i>Acanthocheilonema viteae</i> Product ES-62 Prevents Development of Collagen-Induced Arthritis
  作者：Lamyaa Al-Riyami、Miguel A. Pineda、Justyna Rzepecka、Judith K. Huggan、Abedawn I. Khalaf、Colin J. Suckling、Fraser J. Scott、David T. Rodgers、Margaret M. Harnett、William Harnett

  DOI：10.1021/jm401251p

  日期：2013.12.27

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,
• Evaluation of vinylsulfamides as sulfhydryl selective alkylation reagents in protein modification
  作者：Min Li、Robert S. Wu、Jane S.C. Tsai、Salvatore J. Salamone

  DOI：10.1016/s0960-894x(02)00950-2

  日期：2003.2

  The preparation of several model vinylsulfamides is described. Their excellent selective reactivity towards sulfhydryl group with regards to amino group has been demonstrated by the kinetics study between a model vinylsulfamide and cysteine or lysine at different pHs.

  描述了几种模型乙烯基磺酰胺的制备。通过模型乙烯基磺酰胺与半胱氨酸或赖氨酸在不同pH值之间的动力学研究，证明了它们对氨基而言对巯基的出色的选择性反应性。