sodium 4-(benzyloxy)naphthalene-1-sulfonate | 1429766-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: sodium 4-(benzyloxy)naphthalene-1-sulfonate
• 英文别名: Sodium 4-(benzyloxy)naphthalene-1-sulfonate；sodium;4-phenylmethoxynaphthalene-1-sulfonate
• CAS: 1429766-01-7
• 化学式: C₁₇H₁₃O₄S*Na
• 分子量: 336.344
• InChiKey: BRDBUYUSNJTTBI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium 4-(benzyloxy)naphthalene-1-sulfonate 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 palladium on activated charcoal 、 氢气 、 potassium carbonate 、 1,2-二氯乙烷 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  [EN] SMALL MOLECULE COMPOUNDS TARGETING PBX1 TRANSCRIPTIONAL COMPLEX
  [FR] COMPOSÉS À PETITES MOLÉCULES CIBLANT LE COMPLEXE TRANSCRIPTIONNEL PBX1

  摘要：

  公开号：

  WO2016172437A3
• 作为产物：
  描述：

  sodium 1-naphthol-4-sulfonate 、 溴甲苯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 sodium 4-(benzyloxy)naphthalene-1-sulfonate
  参考文献：
  名称：

  Identification of new dual FABP4/5 inhibitors based on a naphthalene-1-sulfonamide FABP4 inhibitor

  摘要：

  Fatty acid binding protein 4 (FABP4) and fatty acid binding protein 5 (FABP5) are mainly expressed in adipocytes and/or macrophages and play essential roles in energy metabolism and inflammation. When FABP4 function is diminished, FABP5 expression is highly increased possibly as a functional compensation. Dual FABP4/5 inhibitors are expected to provide beneficial synergistic effect on treating diabetes, atherosclerosis, and inflammation-related diseases. Starting from our previously reported selective FABP4 inhibitor 8, structural biology information was used to modulate the selectivity profile and to design potent dual FABP4/5 inhibitors with good selectivity against FABP3. Two compounds A16 and B8 were identified to show inhibitory activities against both FABP4/5 and good selectivity over FABP3, which could also reduce the level of forskolin-stimulated lipolysis in mature 3T3-L1 adipocytes. Compared with compound 8, these two compounds exhibited better anti-inflammatory effects in lipopolysaccharide-stimulated RAW264.7 murine macrophages, with decreased levels of pro-inflammatory cytokines TNF alpha and MCP-1 and apparently inhibited IKK/NF-kappa B pathway.

  DOI：

  10.1016/j.bmc.2019.07.031

文献信息

• SMALL MOLECULE INHIBITORS OF MCL-1 AND THE USES OF THEREOF
  申请人：WAYNE STATE UNIVERSITY

  公开号：US20140235702A1

  公开（公告）日：2014-08-21

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having sulfonamido-1-hydroxynaphthalene structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

  这项发明涉及药物化学领域。具体而言，该发明涉及一类新型小分子，具有磺酰胺基-1-羟基萘结构，可作为Mcl-1蛋白酶抑制剂，并可用作治疗癌症和其他疾病的治疗剂。
• [EN] SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE MCL-1 ET LEURS UTILISATIONS
  申请人：UNIV MICHGIAN

  公开号：WO2013052943A3

  公开（公告）日：2013-06-20
• US9486422B2
  申请人：——

  公开号：US9486422B2

  公开（公告）日：2016-11-08
• Identification of new dual FABP4/5 inhibitors based on a naphthalene-1-sulfonamide FABP4 inhibitor
  作者：Yulong He、Huixia Dou、Dingding Gao、Ting Wang、Mingming Zhang、Heyao Wang、Yingxia Li

  DOI：10.1016/j.bmc.2019.07.031

  日期：2019.10

  Fatty acid binding protein 4 (FABP4) and fatty acid binding protein 5 (FABP5) are mainly expressed in adipocytes and/or macrophages and play essential roles in energy metabolism and inflammation. When FABP4 function is diminished, FABP5 expression is highly increased possibly as a functional compensation. Dual FABP4/5 inhibitors are expected to provide beneficial synergistic effect on treating diabetes, atherosclerosis, and inflammation-related diseases. Starting from our previously reported selective FABP4 inhibitor 8, structural biology information was used to modulate the selectivity profile and to design potent dual FABP4/5 inhibitors with good selectivity against FABP3. Two compounds A16 and B8 were identified to show inhibitory activities against both FABP4/5 and good selectivity over FABP3, which could also reduce the level of forskolin-stimulated lipolysis in mature 3T3-L1 adipocytes. Compared with compound 8, these two compounds exhibited better anti-inflammatory effects in lipopolysaccharide-stimulated RAW264.7 murine macrophages, with decreased levels of pro-inflammatory cytokines TNF alpha and MCP-1 and apparently inhibited IKK/NF-kappa B pathway.
• [EN] SMALL MOLECULE COMPOUNDS TARGETING PBX1 TRANSCRIPTIONAL COMPLEX<br/>[FR] COMPOSÉS À PETITES MOLÉCULES CIBLANT LE COMPLEXE TRANSCRIPTIONNEL PBX1
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2016172437A3

  公开（公告）日：2017-02-16