3′-hydroxypacidamycin D | 1355240-68-4

• 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′-hydroxypacidamycin D
• 英文别名: 3'-OH-pacidamycin D；3'-Hydroxypacidamycin D；(2S)-2-[[(2S)-1-[[(2S,3S)-3-[[(2S)-2-aminopropanoyl]-methylamino]-1-[[(Z)-[(3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylidene]methyl]amino]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 1355240-68-4
• 化学式: C₃₂H₄₁N₉O₁₁
• 分子量: 727.731
• InChiKey: OOMGUJKOXVKRQJ-MNRPCKSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  298
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  在 三氯化硼 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 98.5h， 以22%的产率得到3′-hydroxypacidamycin D
  参考文献：
  名称：

  Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction

  摘要：

  The second-generation synthesis of 3'-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues of mureidomycins. Biological evaluations of these analogues indicated that the stereochemistry at the diaminobutylic acid residue has a crucial impact on both the MraY biochemical inhibition and whole-cell anti-bacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.050

文献信息

• Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction
  作者：Kazuya Okamoto、Masahiro Sakagami、Fei Feng、Fumiyo Takahashi、Kouichi Uotani、Hiroko Togame、Hiroshi Takemoto、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1016/j.bmcl.2012.05.050

  日期：2012.7

  The second-generation synthesis of 3'-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues of mureidomycins. Biological evaluations of these analogues indicated that the stereochemistry at the diaminobutylic acid residue has a crucial impact on both the MraY biochemical inhibition and whole-cell anti-bacterial activity. (C) 2012 Elsevier Ltd. All rights reserved.