3-[3-(2-methoxycarbonyl-2-prop-2-ynyloxycarbonylamino-ethyl)-phenyl]-2-prop-2-ynyloxycarbonylaminopropionic acid methyl ester | 904704-08-1

• 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: 3-[3-(2-methoxycarbonyl-2-prop-2-ynyloxycarbonylamino-ethyl)-phenyl]-2-prop-2-ynyloxycarbonylaminopropionic acid methyl ester
• CAS: 904704-08-1
• 化学式: C₂₂H₂₄N₂O₈
• 分子量: 444.441
• InChiKey: QCEVKPOGNUORDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-[3-(2-methoxycarbonyl-2-prop-2-ynyloxycarbonylamino-ethyl)-phenyl]-2-prop-2-ynyloxycarbonylaminopropionic acid methyl ester 、 2-azidoethyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以73%的产率得到methyl 2-[[1-[2-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]triazol-4-yl]methoxycarbonylamino]-3-[3-[2-[[1-[2-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]triazol-4-yl]methoxycarbonylamino]-3-methoxy-3-oxopropyl]phenyl]propanoate
  参考文献：
  名称：

  Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition

  摘要：

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.028
• 作为产物：
  描述：

  2-benzyloxycarbonylamino-3-[3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-phenyl]-propionic acid methyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 3-[3-(2-methoxycarbonyl-2-prop-2-ynyloxycarbonylamino-ethyl)-phenyl]-2-prop-2-ynyloxycarbonylaminopropionic acid methyl ester
  参考文献：
  名称：

  Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition

  摘要：

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.028