N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide | 721942-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide
• CAS: 721942-76-3
• 化学式: C₂₇H₃₃ClN₂O₁₂
• 分子量: 613.018
• InChiKey: LFTXASSVDPMVHM-GBESBMLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  198.52
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide 在 2,3,5-三甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到[(2R,3S,4R,5R,6R)-3-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-[(3-acetamido-4-chlorophenyl)methoxy]-4,5-dihydroxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049
• 作为产物：
  描述：

  3-amino-4-chlorobenzyl hepta-O-acetyl-β-maltoside 在 甲醇 、 硫酸 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049