methyl o-methylsulfamoylbenzoate | 145889-95-8

• 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: methyl o-methylsulfamoylbenzoate
• 英文别名: methyl (2-methylsulfamoyl)benzoate；Methyl 2-(methylsulfamoyl)benzoate
• CAS: 145889-95-8
• 化学式: C₉H₁₁NO₄S
• mdl: MFCD11646542
• 分子量: 229.257
• InChiKey: NHEROJRIOMGQCA-UHFFFAOYSA-N

物化性质

• 沸点：
  372.6±44.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl o-methylsulfamoylbenzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以280 mg的产率得到2-(hydroxymethyl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Kinase Inhibition via Small Molecule‐Induced Intramolecular Protein Cross‐Linking

  摘要：

  Remarkable progress has been made in the development of cysteine‐targeted covalent inhibitors. In kinase drug discovery, covalent inhibitors capable of targeting other nucleophilic residues (i.e. lysine, or K) have emerged in recent years. Besides a highly conserved catalytic lysine, almost all human protein kinases possess an equally conserved glutamate/aspartate (e.g. E/D) that forms a K–E/D salt bridge within the enzyme's active site. Electrophilic ynamides were previously used as effective peptide coupling reagents and to develop E/D‐targeting covalent protein inhibitors/probes. In the present study, we report the first ynamide‐based small‐molecule inhibitors capable of inducing intramolecular cross‐linking of various protein kinases, leading to subsequent irreversible inhibition of kinase activity. Our strategy took advantage of the close distance between the highly conserved catalytic K and E/D residues in a targeted kinase, thus providing a conceptually general approach to achieve irreversible kinase inhibition with high specificity and desirable cellular potency. Finally, this ynamide‐facilitated, ligand‐induced mechanism leading to intramolecular kinase cross‐linking and inhibition was unequivocally established by using recombinant ABL kinase as a representative.

  DOI：

  10.1002/anie.202404195
• 作为产物：
  描述：

  甲胺 、 2-(氯磺酰基)苯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl o-methylsulfamoylbenzoate
  参考文献：
  名称：

  Kinase Inhibition via Small Molecule‐Induced Intramolecular Protein Cross‐Linking

  摘要：

  Remarkable progress has been made in the development of cysteine‐targeted covalent inhibitors. In kinase drug discovery, covalent inhibitors capable of targeting other nucleophilic residues (i.e. lysine, or K) have emerged in recent years. Besides a highly conserved catalytic lysine, almost all human protein kinases possess an equally conserved glutamate/aspartate (e.g. E/D) that forms a K–E/D salt bridge within the enzyme's active site. Electrophilic ynamides were previously used as effective peptide coupling reagents and to develop E/D‐targeting covalent protein inhibitors/probes. In the present study, we report the first ynamide‐based small‐molecule inhibitors capable of inducing intramolecular cross‐linking of various protein kinases, leading to subsequent irreversible inhibition of kinase activity. Our strategy took advantage of the close distance between the highly conserved catalytic K and E/D residues in a targeted kinase, thus providing a conceptually general approach to achieve irreversible kinase inhibition with high specificity and desirable cellular potency. Finally, this ynamide‐facilitated, ligand‐induced mechanism leading to intramolecular kinase cross‐linking and inhibition was unequivocally established by using recombinant ABL kinase as a representative.

  DOI：

  10.1002/anie.202404195

文献信息

• First domino radical cyclisation/Smiles rearrangement combination
  作者：Marc Pudlo、Ingrid Allart-Simon、Bernard Tinant、Stéphane Gérard、Janos Sapi

  DOI：10.1039/c2cc15670a

  日期：——

  An unprecedented domino radical cyclisation–Smiles rearrangement process affording 3-(2′-aryl-N-methyl acetamido)indolin-2-ones is presented. Experimental rationalisation of this approach and description of an unexpected tricyclic core are also handled.

  提出了一种前所未有的多米诺自由基环化–斯迈尔斯重排过程，生成3-(2′-芳基-N-甲基乙酰胺)吲哚-2-酮。还对该方法的实验合理性进行了阐述，并描述了一个意想不到的三环核心结构。
• STILBENE DERIVATIVE AND METHOD FOR PREPARING SAME
  申请人：Ozchela Inc.

  公开号：US20190248729A1

  公开（公告）日：2019-08-15

  This invention relates to a stilbene derivative and a method of preparing the same, and more particularly to a novel stilbene derivative for inhibiting the function of cyclophilin, which is effective at the prevention of cyclophilin-related diseases or at the treatment of symptoms of such diseases, and to a method of preparing the same.