tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-(3-hydroxypropyl)-6-(4-methoxyphenyl)-4-methylhex-3-enoate | 1361407-69-3

• 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: tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-(3-hydroxypropyl)-6-(4-methoxyphenyl)-4-methylhex-3-enoate
• 英文别名: tert-butyl (E,2R,5R)-2-(3-hydroxypropyl)-6-(4-methoxyphenyl)-4-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enoate
• CAS: 1361407-69-3
• 化学式: C₂₆H₄₁NO₆
• 分子量: 463.615
• InChiKey: CZJVTRDAAMTQIZ-KDVOGPTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-(3-hydroxypropyl)-6-(4-methoxyphenyl)-4-methylhex-3-enoate 在 potassium carbonate 、 苯硫酚 、 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 、 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 (2R,5R,3E)-2-{3-[N-(benzyloxycarbonyl)amino]propyl}-5-[N-(9-fluorenylmethoxycarbonyl)-amino]-6-(4-methoxyphenyl)-4-methylhex-3-enoic acid
  参考文献：
  名称：

  Structure–Activity Relationship Study of a CXC Chemokine Receptor Type 4 Antagonist, FC131, Using a Series of Alkene Dipeptide Isosteres

  摘要：

  A structure-activity relationship study on a highly potent CXC chemokine receptor type 4 (CXCR4) antagonist, FC131 [cyclo(-D-Tyr(1)-Arg(2)-Arg(3)-Nal(4)-Gly(5)-)], was carried out using a series of alkene isosteres of the D-Tyr(1)-L/D-Arg(2) dipeptide to investigate the binding mode of FC131 and its derivatives with CXCR4. The structure-activity relationships of isostere-containing FC131 analogues were similar to those of the parent FC131 and its derivatives, suggesting that a trans-conformer of the D-Tyt(1)-Arg(2) peptide bond is the dominant contributor to the bioactive conformations of FC131. Although NMR analysis demonstrated that the two conformations of the peptidomimetic containing the D-Tyr(1)-D-Arg(2) isostere are possible, binding-mode prediction indicated that the orientations of the alkene motif within D-Tyr(1)-MeArg(2) peptidomimetics depend on the chirality of Arg(2) and the beta-methyl group of the isostere unit, which makes the dominant contribution for binding to the receptor. The most potent FC122 [cyclo(-D-Tyr(1)-D-MeArg(2)-Arg(3)-Nal(4)-Gly(5)-)] bound with CXCR4 by a binding mode different from that of FC131.

  DOI：

  10.1021/jm2016914
• 作为产物：
  描述：

  (R)-N-(tert-butoxycarbonyl)-2-amino-3-(p-methyloxyphenyl)-N-methoxy-N-methylpropionamide 在 六氟合硅酸 、 cerium(III) chloride 、 二甲基硫 、 水 、 copper(l) cyanide 、 sodium hydride 、 臭氧 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 、 乙腈 、 mineral oil 、 正戊烷 为溶剂， 反应 27.5h， 生成 tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-(3-hydroxypropyl)-6-(4-methoxyphenyl)-4-methylhex-3-enoate
  参考文献：
  名称：

  Structure–Activity Relationship Study of a CXC Chemokine Receptor Type 4 Antagonist, FC131, Using a Series of Alkene Dipeptide Isosteres

  摘要：

  A structure-activity relationship study on a highly potent CXC chemokine receptor type 4 (CXCR4) antagonist, FC131 [cyclo(-D-Tyr(1)-Arg(2)-Arg(3)-Nal(4)-Gly(5)-)], was carried out using a series of alkene isosteres of the D-Tyr(1)-L/D-Arg(2) dipeptide to investigate the binding mode of FC131 and its derivatives with CXCR4. The structure-activity relationships of isostere-containing FC131 analogues were similar to those of the parent FC131 and its derivatives, suggesting that a trans-conformer of the D-Tyt(1)-Arg(2) peptide bond is the dominant contributor to the bioactive conformations of FC131. Although NMR analysis demonstrated that the two conformations of the peptidomimetic containing the D-Tyr(1)-D-Arg(2) isostere are possible, binding-mode prediction indicated that the orientations of the alkene motif within D-Tyr(1)-MeArg(2) peptidomimetics depend on the chirality of Arg(2) and the beta-methyl group of the isostere unit, which makes the dominant contribution for binding to the receptor. The most potent FC122 [cyclo(-D-Tyr(1)-D-MeArg(2)-Arg(3)-Nal(4)-Gly(5)-)] bound with CXCR4 by a binding mode different from that of FC131.

  DOI：

  10.1021/jm2016914