癸二酸聚合氮杂环十三烷-2-酮,六氢-2H-吖庚英-2-酮,1,6-己二胺,己二酸,壬烷二酸和哌嗪 | 258834-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 癸二酸聚合氮杂环十三烷-2-酮,六氢-2H-吖庚英-2-酮,1,6-己二胺,己二酸,壬烷二酸和哌嗪
• 英文名称: N-tert-butoxycarbonyl-6-O-tert-butyldimethylsilyl-1-(6-chloropurin-9-yl)-1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-D-allitol
• 英文别名: tert-butyl (3aR,4R,6S,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-[(6-chloropurin-9-yl)methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 258834-91-2
• 化学式: C₂₅H₄₀ClN₅O₅Si
• 分子量: 554.162
• InChiKey: QQPIQHSNHLSTOQ-OGWHTMIXSA-N

物化性质

• 沸点：
  612.1±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  100.83
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  癸二酸聚合氮杂环十三烷-2-酮,六氢-2H-吖庚英-2-酮,1,6-己二胺,己二酸,壬烷二酸和哌嗪 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 16.0h， 以51%的产率得到(2R,3R,4S,5S)-2-Hydroxymethyl-5-(6-hydroxy-purin-9-ylmethyl)-pyrrolidine-3,4-diol
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2
• 作为产物：
  描述：

  5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 sodium tetrahydroborate 、 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 、 mercuric triflate 、 potassium carbonate 、 calcium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 55.0h， 生成 癸二酸聚合氮杂环十三烷-2-酮,六氢-2H-吖庚英-2-酮,1,6-己二胺,己二酸,壬烷二酸和哌嗪
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2