methyl 6-[(E)-2-[4-{(4-bis-ethoxycarbonylmethylene)cyclohexanecarbonylamino}phenyl]-N-(5-methylhexyl)ethenylsulfonamido]hexanoate | 389140-50-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 6-[(E)-2-[4-{(4-bis-ethoxycarbonylmethylene)cyclohexanecarbonylamino}phenyl]-N-(5-methylhexyl)ethenylsulfonamido]hexanoate
• 英文别名: diethyl 2-[4-[[4-[(E)-2-[(6-methoxy-6-oxohexyl)-(5-methylhexyl)sulfamoyl]ethenyl]phenyl]carbamoyl]cyclohexylidene]propanedioate
• CAS: 389140-50-5
• 化学式: C₃₆H₅₄N₂O₉S
• 分子量: 690.899
• InChiKey: GORPTTYXSCOLPM-WNAAXNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  48
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 6-[(E)-2-[4-{(4-bis-ethoxycarbonylmethylene)cyclohexanecarbonylamino}phenyl]-N-(5-methylhexyl)ethenylsulfonamido]hexanoate 在 sodium hydroxide 作用下， 以 丙醇 、 水 为溶剂， 反应 10.0h， 以47%的产率得到trisodium 6-[(E)-2-[4-{(4-bis-carboxymethyl)-3-cyclohexenecarbonylamino}phenyl]-N-(5-methylhexyl)ethenylsulfonamido]hexanoate
  参考文献：
  名称：

  Design and Synthesis of Non-peptidic Inhibitors for the Syk C-Terminal SH2 Domain Based on Structure-Based In-Silico Screening

  摘要：

  Structure-based in-silico screening was carried out for the Syk C-terminal SH2 domain. Fragments that could interact with the pY or pY+1 pockets were selected by our in-silico screening. After tethering two fragments bound to these pockets, we have designed and synthesized new compounds that show favorable interaction with the pY+3 pocket. One such compound, having a cyclohexylmalonic acid moiety identified as a novel potent phosphotyrosyl mimetic, exhibited an affinity comparable to that of the monophosphorylated ligand peptide.

  DOI：

  10.1021/jm010313k
• 作为产物：
  描述：

  4-羰基环己羧酸 在 吡啶 、 四氯化钛 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.08h， 生成 methyl 6-[(E)-2-[4-{(4-bis-ethoxycarbonylmethylene)cyclohexanecarbonylamino}phenyl]-N-(5-methylhexyl)ethenylsulfonamido]hexanoate
  参考文献：
  名称：

  Design and Synthesis of Non-peptidic Inhibitors for the Syk C-Terminal SH2 Domain Based on Structure-Based In-Silico Screening

  摘要：

  Structure-based in-silico screening was carried out for the Syk C-terminal SH2 domain. Fragments that could interact with the pY or pY+1 pockets were selected by our in-silico screening. After tethering two fragments bound to these pockets, we have designed and synthesized new compounds that show favorable interaction with the pY+3 pocket. One such compound, having a cyclohexylmalonic acid moiety identified as a novel potent phosphotyrosyl mimetic, exhibited an affinity comparable to that of the monophosphorylated ligand peptide.

  DOI：

  10.1021/jm010313k

文献信息

• Design and Synthesis of Non-peptidic Inhibitors for the Syk C-Terminal SH2 Domain Based on Structure-Based In-Silico Screening
  作者：Tatsuya Niimi、Masaya Orita、Miwa Okazawa-Igarashi、Hitoshi Sakashita、Kazumi Kikuchi、Evelyn Ball、Atsushi Ichikawa、Yoko Yamagiwa、Shuichi Sakamoto、Akihiro Tanaka、Shinichi Tsukamoto、Shigeo Fujita、Kuniaki Tatsuta、Yasuhide Maeda、Ken Chikauchi

  DOI：10.1021/jm010313k

  日期：2001.12.1

  Structure-based in-silico screening was carried out for the Syk C-terminal SH2 domain. Fragments that could interact with the pY or pY+1 pockets were selected by our in-silico screening. After tethering two fragments bound to these pockets, we have designed and synthesized new compounds that show favorable interaction with the pY+3 pocket. One such compound, having a cyclohexylmalonic acid moiety identified as a novel potent phosphotyrosyl mimetic, exhibited an affinity comparable to that of the monophosphorylated ligand peptide.