3-((2S,5R)-5-Carboxymethyl-3,6-dioxo-piperazin-2-yl)-propionic acid benzyl ester | 325481-59-2

• 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: 3-((2S,5R)-5-Carboxymethyl-3,6-dioxo-piperazin-2-yl)-propionic acid benzyl ester
• 英文别名: 2-[(2R,5S)-3,6-dioxo-5-(3-oxo-3-phenylmethoxypropyl)piperazin-2-yl]acetic acid
• CAS: 325481-59-2
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: CKOOVGTUAAMQFT-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-((2S,5R)-5-Carboxymethyl-3,6-dioxo-piperazin-2-yl)-propionic acid benzyl ester 在 palladium on activated charcoal 氢气 、 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 作用下， 以 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
• 作为产物：
  描述：

  谷氨酸二甲酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 caesium carbonate 、 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 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 生成 3-((2S,5R)-5-Carboxymethyl-3,6-dioxo-piperazin-2-yl)-propionic acid benzyl 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

文献信息

• Bivalent inhibition of β-Tryptase: distance scan of neighboring subunits by dibasic inhibitors
  作者：Norbert Schaschke、Andreas Dominik、Gabriele Matschiner、Christian P. Sommerhoff

  DOI：10.1016/s0960-894x(02)00063-x

  日期：2002.3

  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.