(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide | 269734-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide
• 英文别名: [(2R,3S,4R,5R,6R)-3-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-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
• CAS: 269734-51-2
• 化学式: C₃₀H₃₆ClNO₁₃
• 分子量: 654.068
• InChiKey: UDWNSNOEUSVNOR-ZCSMOAHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  192
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以66%的产率得到(R)-N-[2-chloro-5-[[[2,3-di-O-acetyl-6-O-benzoyl-4-O-(2,3-di-O-acetyl-4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]phenyl]acetamide
  参考文献：
  名称：

  Acetal benzylmaltosides as inhibitors of smooth muscle cell proliferation

  摘要：

  本发明提供了具有本文定义的变量结构的式I平滑肌细胞增殖抑制剂。

  公开号：

  US06340670B1
• 作为产物：
  描述：

  4-氯-3-硝基苯甲醇 在 2,3,5-三甲基吡啶 、 甲醇 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 、 三乙胺 、 mercury dibromide 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 29.5h， 生成 (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]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

文献信息

• ACETAL BENZYLMALTOSIDES AS INHIBITORS OF SMOOTH MUSCLE CELL PROLIFERATION
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1133509A1

  公开（公告）日：2001-09-19
• US6340670B1
  申请人：——

  公开号：US6340670B1

  公开（公告）日：2002-01-22
• [EN] ACETAL BENZYLMALTOSIDES AS INHIBITORS OF SMOOTH MUSCLE CELL PROLIFERATION<br/>[FR] BENZYLMALTOSIDES ACETAL UTILISES COMME INHIBITEURS DE LA PROLIFERATION CELLULAIRE DES MUSCLES LISSES
  申请人：AMERICAN HOME PROD

  公开号：WO2000031096A1

  公开（公告）日：2000-06-02

  This invention provides smooth muscle cell proliferation inhibitors of formula (I), having structure (I), wherein X, R?1, R2, R3, R4, R5, R6, R7, R8 and R9¿ have the meaning given in the claims and description.
• Acetal benzylmaltosides as inhibitors of smooth muscle cell proliferation
  申请人：American Home Products Corporation

  公开号：US06340670B1

  公开（公告）日：2002-01-22

  This invention provides smooth muscle cell proliferation inhibitors of formula I having the structure with the variables defined herein.

  本发明提供了具有本文定义的变量结构的式I平滑肌细胞增殖抑制剂。
• Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation
  作者：Scott C. Mayer、William Gallaway、John Kulishoff、Maisheng Yin、Vidya Gadamasetti、Robert Mitchell

  DOI：10.1016/j.bmcl.2004.03.049

  日期：2004.6

  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.