4-(((4-fluorobenzyl)(pyridin-2-ylmethyl)amino)methyl)-N-((S)-5-(3-(mesitylsulfonyl)guanidino)-1-(((S)-1-(naphthalen-1-yl)ethyl)amino)-1-oxopentan-2-yl)benzamide | 1383122-98-2

• 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: 4-(((4-fluorobenzyl)(pyridin-2-ylmethyl)amino)methyl)-N-((S)-5-(3-(mesitylsulfonyl)guanidino)-1-(((S)-1-(naphthalen-1-yl)ethyl)amino)-1-oxopentan-2-yl)benzamide
• CAS: 1383122-98-2
• 化学式: C₄₈H₅₂FN₇O₄S
• 分子量: 842.05
• InChiKey: HESDDRJBLXVAPD-BTDRIEDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  156.38
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(((4-fluorobenzyl)(pyridin-2-ylmethyl)amino)methyl)-N-((S)-5-(3-(mesitylsulfonyl)guanidino)-1-(((S)-1-(naphthalen-1-yl)ethyl)amino)-1-oxopentan-2-yl)benzamide 在 三甲基溴硅烷 、 茴香硫醚 、 1,2-乙二硫醇 、 间甲酚 、 三氟乙酸 作用下， 反应 3.5h， 以13%的产率得到4-[[(4-fluorophenyl)methyl-(2-pyridylmethyl)amino]methyl]-N-[(1S)-4-guanidino-1-[[(1S)-1-(1-naphthyl)ethyl]carbamoyl]butyl]benzamide
  参考文献：
  名称：

  Pharmacophore-based small molecule CXCR4 ligands

  摘要：

  Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure-activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.032
• 作为产物：
  描述：

  4-氨甲基苯甲酸 在 硫酸 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 苯硫酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 4-(((4-fluorobenzyl)(pyridin-2-ylmethyl)amino)methyl)-N-((S)-5-(3-(mesitylsulfonyl)guanidino)-1-(((S)-1-(naphthalen-1-yl)ethyl)amino)-1-oxopentan-2-yl)benzamide
  参考文献：
  名称：

  Pharmacophore-based small molecule CXCR4 ligands

  摘要：

  Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure-activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.032