3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester | 325774-13-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester
• CAS: 325774-13-8
• 化学式: C₂₇H₃₇N₅O₁₀
• 分子量: 591.618
• InChiKey: JJMNDBMYQFVIBX-PAMZHZACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  218.33
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(3-Aminomethyl-phenyl)-2-{2-[2-((2R,5S)-5-{2-[2-(3-aminomethyl-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-ethyl}-3,6-dioxo-piperazin-2-yl)-acetylamino]-acetylamino}-propionic acid methyl ester
  参考文献：
  名称：

  Bivalent inhibition of β-Tryptase: distance scan of neighboring subunits by dibasic inhibitors

  摘要：

  Based on bifunctional diketopiperazines as templates and m-aminomethyl-phenylalanine as arginine mimetic, we have synthesized a new class of structurally related dibasic tryptase inhibitors with systematically increasing spacer length. These compounds were used to scan the distance between the active sites of two neighboring subunits of the beta-tryptase tetramer. The K-i-values obtained are a function of the distance between the terminal amino groups and indicate optimal binding of inhibitors with 29-31 bonds between the amino groups. These experimental data are in full agreement with predictions derived from a novel modeling program that allows the docking of bivalent ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00063-x
• 作为产物：
  描述：

  3-(3-Cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester 在 palladium on activated charcoal 氢气 、 乙酸肼 、 碳酸氢钠 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Bivalent inhibition of β-Tryptase: distance scan of neighboring subunits by dibasic inhibitors

  摘要：

  Based on bifunctional diketopiperazines as templates and m-aminomethyl-phenylalanine as arginine mimetic, we have synthesized a new class of structurally related dibasic tryptase inhibitors with systematically increasing spacer length. These compounds were used to scan the distance between the active sites of two neighboring subunits of the beta-tryptase tetramer. The K-i-values obtained are a function of the distance between the terminal amino groups and indicate optimal binding of inhibitors with 29-31 bonds between the amino groups. These experimental data are in full agreement with predictions derived from a novel modeling program that allows the docking of bivalent ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00063-x