N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide | 1016950-44-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide
• 英文别名: N-[7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]benzenesulfonamide
• CAS: 1016950-44-9
• 化学式: C₂₄H₂₇NO₉S
• 分子量: 505.546
• InChiKey: PDAGPFGPOIRXPH-KLJZETAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide 、 N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)-2-phenylacetamide 以 溶剂黄146 为溶剂， 生成 benzyl 8-ethyl-7-hydroxy-2-oxo-2H-chromen-3-ylcarbamate
  参考文献：
  名称：

  NOVOBIOCIN ANALOGUES AND TREATMENT OF POLYCYSTIC KIDNEY DISEASE

  摘要：

  新比奴霉素类似物在治疗、抑制和/或预防自体显性多囊肾病（ADPKD）中的囊肿形成方法中是有用的。本公开提供了治疗ADPKD的方法，包括给予香豆素-3-羧酰胺新比奴霉素类似物的治疗有效量。因此，该方法可以包括给予新比奴霉素类似物的治疗有效量，以降低mTOR途径磷酸化蛋白P-mTOR、P-Akt和P-S6K的水平，或其组合。此外，该方法可以包括给予新比奴霉素类似物的治疗有效量，以降低Hsp-90客体蛋白CFTR、ErbB2、c-Raf和Cdk4的水平，或其组合。

  公开号：

  US20110082098A1
• 作为产物：
  描述：

  N-(7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以79%的产率得到N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Development of Novobiocin Analogues That Manifest Anti-proliferative Activity against Several Cancer Cell Lines

  摘要：

  Recent studies have shown that the DNA gyrase inhibitor, novobiocin, binds to a previously unrecognized ATP-binding site located at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at similar to 700 mu M. As a result of these studies, several analogues of the coumarin family of antibiotics have been reported and shown to exhibit increased Hsp90 inhibitory activity; however, the monomeric species lacked the ability to manifest anti-proliferative activity against cancer cell lines at concentrations tested. In an effort to develop more efficacious compounds that produce growth inhibitory activity against cancer cell lines, structure-activity relationships; were investigated surrounding the prenylated benzamide side chain of the natural product. Results obtained from these studies have produced the first novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.

  DOI：

  10.1021/jo702191a

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 S. J.

  公开号：US09120774B2

  公开（公告）日：2015-09-01

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

  该披露提供了替代noviose的新比素类似物，可用于治疗癌症中的Hsp90抑制剂。
• 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