(2S,3S)-2-tert-Butoxycarbonylamino-3-[2-(3,3-diphenyl-propionyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-4-yl]-3-hydroxy-propionic acid methyl ester | 876404-32-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-tert-Butoxycarbonylamino-3-[2-(3,3-diphenyl-propionyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-4-yl]-3-hydroxy-propionic acid methyl ester
• CAS: 876404-32-9
• 化学式: C₃₁H₃₉N₃O₈
• 分子量: 581.666
• InChiKey: WJUZAWZPXQAKEP-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  138.21
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-tert-Butoxycarbonylamino-3-[2-(3,3-diphenyl-propionyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-4-yl]-3-hydroxy-propionic acid methyl ester 在 盐酸 、 甲醇 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 31.0h， 以75%的产率得到(2S,3S)-2-Amino-3-[2-(3,3-diphenyl-propionyl)-1H-imidazol-4-yl]-3-hydroxy-propionic acid methyl ester; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Side-chain modified analogues of histaprodifen: Asymmetric synthesis and histamine H1-receptor activity

  摘要：

  New analogues of histaprodifen with polar side chains have been stereo selectively synthesized and evaluated as histamine H-1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H-1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H-1-receptor agonism (relative potency 12%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.030
• 作为产物：
  描述：

  (E)-3-[1-(2-Methoxy-ethoxymethyl)-1H-imidazol-4-yl]-acrylic acid methyl ester 在 potassium dioxotetrahydroxoosmate(VI) 、 hydroquinidine anthraquinone-1,4-diyl diether 、 sodium [(benzyloxy)carbonyl]chloroamide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.0h， 生成 (2S,3S)-2-tert-Butoxycarbonylamino-3-[2-(3,3-diphenyl-propionyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-4-yl]-3-hydroxy-propionic acid methyl ester
  参考文献：
  名称：

  Side-chain modified analogues of histaprodifen: Asymmetric synthesis and histamine H1-receptor activity

  摘要：

  New analogues of histaprodifen with polar side chains have been stereo selectively synthesized and evaluated as histamine H-1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H-1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H-1-receptor agonism (relative potency 12%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.030