(S)-6-benzyloxycarbonylamino-2-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetylamino]hexanoic acid | 1067665-27-3

• 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: (S)-6-benzyloxycarbonylamino-2-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetylamino]hexanoic acid
• 英文别名: N^α-[(thymin-1-yl)acetyl]-N^ε-(benzyloxycarbonyl)-L-lysine；(2S)-2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]-6-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 1067665-27-3
• 化学式: C₂₁H₂₆N₄O₇
• 分子量: 446.46
• InChiKey: WEUKBYHMZXFRLF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-6-benzyloxycarbonylamino-2-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetylamino]hexanoic acid 在 三氟甲磺酸三甲基硅酯 茴香硫醚 、 WSC*HCl 、 间甲酚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 6'-N-[N^α-[(thymin-1-yl)acetyl]-DL-lysyl]neamine
  参考文献：
  名称：

  Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR–Tat

  摘要：

  Neamine derivatives hearing a nucleobase, adenine, cytosine. guanine or thymine with a lysine or an arginine as a linker have been synthesized and its potential as the inhibitor for HIV TAR-Tat interaction examined. Among them, modified neamine having an arginine-nucleobase showed a higher inhibition than that of the one having a lysine-nuclcobase. The difference of the nucleobase anchor did not characterize inhibition specificity. Also, stereochemistry of the amino acid in the compounds causes no difference in the inhibition for TAR-Tat. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.056
• 作为产物：
  描述：

  tert-butyl N^α-[(thymin-1-yl)acetyl]-N^ε-(benzyloxycarbonyl)-L-lysinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以99.2%的产率得到(S)-6-benzyloxycarbonylamino-2-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetylamino]hexanoic acid
  参考文献：
  名称：

  Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR–Tat

  摘要：

  Neamine derivatives hearing a nucleobase, adenine, cytosine. guanine or thymine with a lysine or an arginine as a linker have been synthesized and its potential as the inhibitor for HIV TAR-Tat interaction examined. Among them, modified neamine having an arginine-nucleobase showed a higher inhibition than that of the one having a lysine-nuclcobase. The difference of the nucleobase anchor did not characterize inhibition specificity. Also, stereochemistry of the amino acid in the compounds causes no difference in the inhibition for TAR-Tat. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.056

文献信息

• Chiral peptide nucleic acid monomers (PNAM) with modified backbones
  作者：Alan Roy Katritzky、Tamari Narindoshvili

  DOI：10.1039/b806141f

  日期：——

  of optically pure PNAMs comprising l- or d-serine, l-lysine and l-arginine units linked to thymine or Cbz-cytosine are described. Simple workup and inexpensive reagents are employed and free amino acids are used as coupling components.

  描述了包含与胸腺嘧啶或Cbz-胞嘧啶连接的1-或d-丝氨酸，1-赖氨酸和1-精氨酸单元的光学纯PNAM的方便的高产率合成。使用简单的后处理和廉价的试剂，并且将游离氨基酸用作偶联组分。
• Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR–Tat
  作者：Saki Yajima、Hirohito Shionoya、Takashi Akagi、Keita Hamasaki

  DOI：10.1016/j.bmc.2005.11.056

  日期：2006.4

  Neamine derivatives hearing a nucleobase, adenine, cytosine. guanine or thymine with a lysine or an arginine as a linker have been synthesized and its potential as the inhibitor for HIV TAR-Tat interaction examined. Among them, modified neamine having an arginine-nucleobase showed a higher inhibition than that of the one having a lysine-nuclcobase. The difference of the nucleobase anchor did not characterize inhibition specificity. Also, stereochemistry of the amino acid in the compounds causes no difference in the inhibition for TAR-Tat. (c) 2005 Elsevier Ltd. All rights reserved.