N-(4-methoxybenzyl)-N-{6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy]naphthalen-2-yl}-4-methoxy-3-(3-methoxyphenyl)benzamide | 1083314-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-methoxybenzyl)-N-{6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy]naphthalen-2-yl}-4-methoxy-3-(3-methoxyphenyl)benzamide
• 英文别名: N-[6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxynaphthalen-2-yl]-4-methoxy-3-(3-methoxyphenyl)-N-[(4-methoxyphenyl)methyl]benzamide
• CAS: 1083314-03-7
• 化学式: C₄₁H₄₃NO₉
• 分子量: 693.794
• InChiKey: BBCDBJCKFPIDCF-VVQBALQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-[6-[[(3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]naphthalen-2-yl]-4-methoxy-3-(3-methoxyphenyl)-N-[(4-methoxyphenyl)methyl]benzamide 在 甲醇 、 三乙胺 作用下， 反应 18.0h， 以27 mg的产率得到N-(4-methoxybenzyl)-N-{6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy]naphthalen-2-yl}-4-methoxy-3-(3-methoxyphenyl)benzamide
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold that Exhibit Antiproliferative Activity

  摘要：

  Novobiocin, a known DNA gyrase inhibitor, binds to a nucleotide-binding site located on the Hsp90 C-terminus and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M in breast cancer cells (SKBr3). Although many analogues of novobiocin have been synthesized, it was only recently demonstrated that monomeric species exhibit antiproliferative activity against various cancer cell lines. To further refine the essential elements of the coumarin core, a series of modified coumarin derivatives was, synthesized and evaluated to elucidate structure-activity relationships for novobiocin as an anticancer agent. Results obtained from these studies have produced novobiocin analogues that manifest low micromolar activity against several cancer cell lines.

  DOI：

  10.1021/jo801312r

文献信息

• NOVOBIOCIN ANALOGUES HAVING MODIFIED SUGAR MOIETIES
  申请人：Blagg Brian S. J.

  公开号：US20120252745A1

  公开（公告）日：2012-10-04

  The disclosure provides novobiocin analogues with noviose replacements which are useful as Hsp90 inhibitors in the treatment of cancer.

  本公开提供了具有替代noviose的诺维菌素类似物，其在癌症治疗中作为Hsp90抑制剂是有用的。
• Novobiocin Analogues Having Modified Sugar Moieties
  申请人：Blagg Brian

  公开号：US20090163709A1

  公开（公告）日：2009-06-25

  Novobiocin analogues useful as Hsp90 inhibitors in the treatment of cancer, neuroprotection, and autoimmune disorders.

  诺伐霉素类似物在癌症、神经保护和自身免疫性疾病的治疗中作为Hsp90抑制剂有用。
• Novobiocin Analogues
  申请人：Blagg Brian

  公开号：US20090187014A1

  公开（公告）日：2009-07-23

  Novobiocin analogues and pharmaceutical composition containing such compounds useful for the treatment and/or prevention of neurodegenerative disorders and autoimmune disorders, as well as cancer.

  Novobiocin类似物和含有这些化合物的药物组合物，可用于治疗和/或预防神经退行性疾病、自身免疫性疾病以及癌症。
• US8212012B2
  申请人：——

  公开号：US8212012B2

  公开（公告）日：2012-07-03
• US8212011B2
  申请人：——

  公开号：US8212011B2

  公开（公告）日：2012-07-03