(2-trimethylsilanylethyl)-3-cyano-5-(4-methoxybenzyl)benzoate | 869096-85-5

• 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: (2-trimethylsilanylethyl)-3-cyano-5-(4-methoxybenzyl)benzoate
• 英文别名: 2-Trimethylsilylethyl 3-cyano-5-[(4-methoxyphenyl)methyl]benzoate
• CAS: 869096-85-5
• 化学式: C₂₁H₂₅NO₃Si
• 分子量: 367.52
• InChiKey: DDLCWONFLQBQLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-trimethylsilanylethyl)-3-cyano-5-(4-methoxybenzyl)benzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.33h， 生成 3-aminomethyl-5-(4-methoxy-benzyl)-benzoic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Angiotensin II Pseudopeptides Containing 1,3,5-Trisubstituted Benzene Scaffolds with High AT₂ Receptor Affinity

  摘要：

  Two 1,3,5-trisubstituted aromatic scaffolds intended to serve as gamma-turn mimetics have been synthesized and incorporated in five pseudopeptide analogues of angiotensin II (Asp-Arg-Val-Tyr-Ile-His-Pro-Phe), replacing Val-Tyr-Ile, Val-Tyr, or Tyr-Ile. All the tested compounds exhibited nanomolar affinity for the AT(2) receptor with the best compound (3) having a K-i of 1.85 nM. Four pseudopeptides were AT(2) selective, while one (5) also exhibited good affinity for the AT(1) receptor (K-i = 30.3 nM). This pseudopeptide exerted full agonistic activity in an AT(2) receptor induced neurite outgrowth assay but displayed no agonistic effect in an AT(2) receptor functional assay. Molecular modeling, using the program DISCOtech, showed that the high-affinity ligands could interact similarly with the AT(2) receptor as other ligands with high affinity for this receptor. A tentative agonist model is proposed for AT(2) receptor activation by angiotensin 11 analogues. We conclude that the 1,3,5-trisubstituted benzene rings can be conveniently prepared and are suitable as gamma-turn mimics.

  DOI：

  10.1021/jm050280z
• 作为产物：
  描述：

  3-bromo-5-iodobenzoyl chloride 在 palladium on activated charcoal 、 钯 三乙基硅烷 、 4-二甲氨基吡啶 、 三氯化铝 、 三氟甲磺酸 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.42h， 生成 (2-trimethylsilanylethyl)-3-cyano-5-(4-methoxybenzyl)benzoate
  参考文献：
  名称：

  Angiotensin II Pseudopeptides Containing 1,3,5-Trisubstituted Benzene Scaffolds with High AT₂ Receptor Affinity

  摘要：

  Two 1,3,5-trisubstituted aromatic scaffolds intended to serve as gamma-turn mimetics have been synthesized and incorporated in five pseudopeptide analogues of angiotensin II (Asp-Arg-Val-Tyr-Ile-His-Pro-Phe), replacing Val-Tyr-Ile, Val-Tyr, or Tyr-Ile. All the tested compounds exhibited nanomolar affinity for the AT(2) receptor with the best compound (3) having a K-i of 1.85 nM. Four pseudopeptides were AT(2) selective, while one (5) also exhibited good affinity for the AT(1) receptor (K-i = 30.3 nM). This pseudopeptide exerted full agonistic activity in an AT(2) receptor induced neurite outgrowth assay but displayed no agonistic effect in an AT(2) receptor functional assay. Molecular modeling, using the program DISCOtech, showed that the high-affinity ligands could interact similarly with the AT(2) receptor as other ligands with high affinity for this receptor. A tentative agonist model is proposed for AT(2) receptor activation by angiotensin 11 analogues. We conclude that the 1,3,5-trisubstituted benzene rings can be conveniently prepared and are suitable as gamma-turn mimics.

  DOI：

  10.1021/jm050280z

文献信息

• Angiotensin II Pseudopeptides Containing 1,3,5-Trisubstituted Benzene Scaffolds with High AT₂ Receptor Affinity
  作者：Jennie Georgsson、Christian Sköld、Bianca Plouffe、Gunnar Lindeberg、Milad Botros、Mats Larhed、Fred Nyberg、Nicole Gallo-Payet、Adolf Gogoll、Anders Karlén、Anders Hallberg

  DOI：10.1021/jm050280z

  日期：2005.10.1

  Two 1,3,5-trisubstituted aromatic scaffolds intended to serve as gamma-turn mimetics have been synthesized and incorporated in five pseudopeptide analogues of angiotensin II (Asp-Arg-Val-Tyr-Ile-His-Pro-Phe), replacing Val-Tyr-Ile, Val-Tyr, or Tyr-Ile. All the tested compounds exhibited nanomolar affinity for the AT(2) receptor with the best compound (3) having a K-i of 1.85 nM. Four pseudopeptides were AT(2) selective, while one (5) also exhibited good affinity for the AT(1) receptor (K-i = 30.3 nM). This pseudopeptide exerted full agonistic activity in an AT(2) receptor induced neurite outgrowth assay but displayed no agonistic effect in an AT(2) receptor functional assay. Molecular modeling, using the program DISCOtech, showed that the high-affinity ligands could interact similarly with the AT(2) receptor as other ligands with high affinity for this receptor. A tentative agonist model is proposed for AT(2) receptor activation by angiotensin 11 analogues. We conclude that the 1,3,5-trisubstituted benzene rings can be conveniently prepared and are suitable as gamma-turn mimics.