2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl methanesulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl methanesulfonate
• 英文别名: 4-(4-butyl-1H-1,2,3-triazol-1-yl)phenethyl methanesulfonate；2-[4-(4-Butyltriazol-1-yl)phenyl]ethyl methanesulfonate；2-[4-(4-butyltriazol-1-yl)phenyl]ethyl methanesulfonate
• 化学式: C₁₅H₂₁N₃O₃S
• 分子量: 323.416
• InChiKey: DHCMXWMAXOLLKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基哌啶 、 2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl methanesulfonate 以 乙腈 为溶剂， 反应 12.0h， 以82%的产率得到1-(2-(4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl)ethyl)-1-methylpiperidin-1-ium methanesulfonate
  参考文献：
  名称：

  Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors

  摘要：

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.

  DOI：

  10.1021/jm401399c
• 作为产物：
  描述：

  4-氨基苯乙醇 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 54.5h， 生成 2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl methanesulfonate
  参考文献：
  名称：

  Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors

  摘要：

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.

  DOI：

  10.1021/jm401399c

文献信息

• [EN] SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS ET ACTIVATEURS ALLOSTÉRIQUES DE LA SPHINGOSINE KINASE
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2014118556A3

  公开（公告）日：2014-09-25