3-tert-butoxycarbonylamino-2-hydroxy-propionaldehyde diethyl acetal | 182680-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-tert-butoxycarbonylamino-2-hydroxy-propionaldehyde diethyl acetal
• 英文别名: tert-butyl N-(3,3-diethoxy-2-hydroxypropyl)carbamate
• CAS: 182680-63-3
• 化学式: C₁₂H₂₅NO₅
• 分子量: 263.334
• InChiKey: HKVLCCKDWSMXFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-tert-butoxycarbonylamino-2-hydroxy-propionaldehyde diethyl acetal 在 盐酸 作用下， 反应 0.03h， 以20%的产率得到3-amino-1-hydroxypropan-2-one hydrochloride
  参考文献：
  名称：

  3-Amino-2-hydroxy-propionaldehyde and 3-amino-1-hydroxypropan-2-one derivatives: New classes of aminopeptidase inhibitors

  摘要：

  3-Amino-2-hydroxy-propionaldehydes [H2NCH(R)CHOHCHO with R = H, i-Bu, CH(2)Ph] were designed as metallo-aminopeptidase inhibitors based on the metal active site chelation concept. These compounds were found to be micromolar inhibitors of aminopeptidase-M (AP-M, EC 3.4.11.2) with potencies similar to bestatin (K-i = 3.5 mu M). Notably, compound 5a (R = H) is a selective inhibitor of AP-M (K-i = 7 mu M) with respect to cytosolic leucine aminopeptidase (LAPc, EC 3.4.11.1) (K-i = 385 mu M). However, due to their easy oligomerization, these compounds are of low practical value. In contrast, the corresponding isomeric 3-amino-1-hydroxy-propan-2-one derivatives [H2NCH(R)COCH2OH with R = H, i-Bu, CH(2)Ph, i-Pr, CH(2)Biph] are well defined structures. These hydroxymethylketones also exhibit micromolar affinities on AP-M. Compound 6c (R = CH,Ph) was the most potent (K-i = 1 mu M). Selectivity studies of 6a (R = H) and 6b (R = i-Bu) show a preference for AP-M. Compound 6a is moderately active on AP-M (K-i = 25 mu M) and inactive on LAPc. This new class of inhibitors is proposed to bind as bidentates, analogous to hydroxamates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00115-0
• 作为产物：
  描述：

  1,1-diethoxy-3-nitro-propan-2-ol 在 镍 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 3-tert-butoxycarbonylamino-2-hydroxy-propionaldehyde diethyl acetal
  参考文献：
  名称：

  3-Amino-2-hydroxy-propionaldehyde and 3-amino-1-hydroxypropan-2-one derivatives: New classes of aminopeptidase inhibitors

  摘要：

  3-Amino-2-hydroxy-propionaldehydes [H2NCH(R)CHOHCHO with R = H, i-Bu, CH(2)Ph] were designed as metallo-aminopeptidase inhibitors based on the metal active site chelation concept. These compounds were found to be micromolar inhibitors of aminopeptidase-M (AP-M, EC 3.4.11.2) with potencies similar to bestatin (K-i = 3.5 mu M). Notably, compound 5a (R = H) is a selective inhibitor of AP-M (K-i = 7 mu M) with respect to cytosolic leucine aminopeptidase (LAPc, EC 3.4.11.1) (K-i = 385 mu M). However, due to their easy oligomerization, these compounds are of low practical value. In contrast, the corresponding isomeric 3-amino-1-hydroxy-propan-2-one derivatives [H2NCH(R)COCH2OH with R = H, i-Bu, CH(2)Ph, i-Pr, CH(2)Biph] are well defined structures. These hydroxymethylketones also exhibit micromolar affinities on AP-M. Compound 6c (R = CH,Ph) was the most potent (K-i = 1 mu M). Selectivity studies of 6a (R = H) and 6b (R = i-Bu) show a preference for AP-M. Compound 6a is moderately active on AP-M (K-i = 25 mu M) and inactive on LAPc. This new class of inhibitors is proposed to bind as bidentates, analogous to hydroxamates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00115-0

文献信息

• 3-Amino-2-hydroxy-propionaldehyde and 3-amino-1-hydroxypropan-2-one derivatives: New classes of aminopeptidase inhibitors
  作者：Céline Tarnus、Jean-Marc Rémy、Hugues d'Orchymont

  DOI：10.1016/0968-0896(96)00115-0

  日期：1996.8

  3-Amino-2-hydroxy-propionaldehydes [H2NCH(R)CHOHCHO with R = H, i-Bu, CH(2)Ph] were designed as metallo-aminopeptidase inhibitors based on the metal active site chelation concept. These compounds were found to be micromolar inhibitors of aminopeptidase-M (AP-M, EC 3.4.11.2) with potencies similar to bestatin (K-i = 3.5 mu M). Notably, compound 5a (R = H) is a selective inhibitor of AP-M (K-i = 7 mu M) with respect to cytosolic leucine aminopeptidase (LAPc, EC 3.4.11.1) (K-i = 385 mu M). However, due to their easy oligomerization, these compounds are of low practical value. In contrast, the corresponding isomeric 3-amino-1-hydroxy-propan-2-one derivatives [H2NCH(R)COCH2OH with R = H, i-Bu, CH(2)Ph, i-Pr, CH(2)Biph] are well defined structures. These hydroxymethylketones also exhibit micromolar affinities on AP-M. Compound 6c (R = CH,Ph) was the most potent (K-i = 1 mu M). Selectivity studies of 6a (R = H) and 6b (R = i-Bu) show a preference for AP-M. Compound 6a is moderately active on AP-M (K-i = 25 mu M) and inactive on LAPc. This new class of inhibitors is proposed to bind as bidentates, analogous to hydroxamates. Copyright (C) 1996 Elsevier Science Ltd