benzyl 2-(benzyloxy)-4-(2-(4-chloro-N-methylphenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate | 1334493-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl 2-(benzyloxy)-4-(2-(4-chloro-N-methylphenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate
• CAS: 1334493-29-6
• 化学式: C₄₇H₄₆N₂O₆S
• 分子量: 766.958
• InChiKey: MXXYMEXDZQXPNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-(benzyloxy)-4-(2-(4-chloro-N-methylphenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以87%的产率得到4-(N-(4-cyclohexylbenzyl)-2-(N-methylnaphthalene-2-sulfonamido)acetamido)-2-hydroxybenzoic acid
  参考文献：
  名称：

  Identification of a non-phosphorylated, cell permeable, small molecule ligand for the Stat3 SH2 domain

  摘要：

  Signal transducer and activator of transcription 3 (Stat3) protein is a cytosolic transcription factor that is aberrantly activated in numerous human cancers. Inhibitors of activated Stat3-Stat3 protein complexes have been shown to hold therapeutic promise for the treatment of human cancers harboring activated Stat3. Herein, we report the design and synthesis of a focused library of salicylic acid containing Stat3 SH2 domain binders. The most potent inhibitor, 17o, effectively disrupted Stat3-phosphopeptide complexes (K(i) = 13 mu M), inhibited Stat3-Stat3 protein interactions (IC(50) = 19 mu M) and silenced intracellular Stat3 phosphorylation and Stat3-target gene expression profiles. Inhibition of Stat3 function in both breast and multiple myeloma (MM) tumor cells correlated with induced cell death (EC(50) = 10 and 16 mu M, respectively). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.056
• 作为产物：
  描述：

  4-氨基水杨酸 在 lithium hydroxide monohydrate 、 potassium tert-butylate 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基二氯化膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.42h， 生成 benzyl 2-(benzyloxy)-4-(2-(4-chloro-N-methylphenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate
  参考文献：
  名称：

  Identification of a non-phosphorylated, cell permeable, small molecule ligand for the Stat3 SH2 domain

  摘要：

  Signal transducer and activator of transcription 3 (Stat3) protein is a cytosolic transcription factor that is aberrantly activated in numerous human cancers. Inhibitors of activated Stat3-Stat3 protein complexes have been shown to hold therapeutic promise for the treatment of human cancers harboring activated Stat3. Herein, we report the design and synthesis of a focused library of salicylic acid containing Stat3 SH2 domain binders. The most potent inhibitor, 17o, effectively disrupted Stat3-phosphopeptide complexes (K(i) = 13 mu M), inhibited Stat3-Stat3 protein interactions (IC(50) = 19 mu M) and silenced intracellular Stat3 phosphorylation and Stat3-target gene expression profiles. Inhibition of Stat3 function in both breast and multiple myeloma (MM) tumor cells correlated with induced cell death (EC(50) = 10 and 16 mu M, respectively). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.056