2-methoxy-3,6-bis(methoxymethoxy)-5-nitrophenethyl 3-chloro-4,6-dihydroxy-2-(pent-4-enyl)benzoate | 913622-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-3,6-bis(methoxymethoxy)-5-nitrophenethyl 3-chloro-4,6-dihydroxy-2-(pent-4-enyl)benzoate
• 英文别名: 2-[2-Methoxy-3,6-bis(methoxymethoxy)-5-nitrophenyl]ethyl 3-chloro-4,6-dihydroxy-2-pent-4-enylbenzoate
• CAS: 913622-86-3
• 化学式: C₂₅H₃₀ClNO₁₁
• 分子量: 555.966
• InChiKey: OHVOHAVRAYSPGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-methoxy-3,6-bis(methoxymethoxy)-5-nitrophenethyl 3-chloro-4,6-dihydroxy-2-(pent-4-enyl)benzoate 在 palladium on activated charcoal 2,6-二甲基吡啶 、 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 四氧化锇 、 三甲基氯硅烷 、 2-甲基-2-丁烯 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium iodide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 20.83h， 生成 10-Chloro-7,9,19,21-tetrahydroxy-20-methoxy-4-oxa-16-aza-tricyclo[15.3.1.0^6,11]henicosa-1(21),6(11),7,9,17,19-hexaene-5,15-dione
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f
• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 硝酸铵 、 正丁基锂 、 四甲基乙二胺 、 偶氮二甲酸二异丙酯 、 sodium hydride 、 三苯基膦 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 16.33h， 生成 2-methoxy-3,6-bis(methoxymethoxy)-5-nitrophenethyl 3-chloro-4,6-dihydroxy-2-(pent-4-enyl)benzoate
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f