methyl 3-chloro-2-[2-(2,5-dihydroxy-4-methoxyphenylcarbamoyl)ethyl]-4,6-dihydroxybenzoate | 811788-21-3

• 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: methyl 3-chloro-2-[2-(2,5-dihydroxy-4-methoxyphenylcarbamoyl)ethyl]-4,6-dihydroxybenzoate
• 英文别名: Methyl 3-Chloro-2-{3-[(2,5-Dihydroxy-4-Methoxyphenyl)amino]-3-Oxopropyl}-4,6-Dihydroxybenzoate；methyl 3-chloro-2-[3-(2,5-dihydroxy-4-methoxyanilino)-3-oxopropyl]-4,6-dihydroxybenzoate
• CAS: 811788-21-3
• 化学式: C₁₈H₁₈ClNO₈
• 分子量: 411.796
• InChiKey: GUVWEHNRWHNDRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-chloro-2-[2-(2,5-dihydroxy-4-methoxyphenylcarbamoyl)ethyl]-4,6-dihydroxybenzoate 在 palladium on activated charcoal 作用下， 以69%的产率得到Radamide
  参考文献：
  名称：

  Heat shock protein 90 inhibitors

  摘要：

  新型化合物对抑制含有类似醌类结构和二羟基酚类结构的90千道尔顿热休克蛋白具有用途，类似于格尔德霉素和拉迪考尔。

  公开号：

  US20060089495A1
• 作为产物：
  描述：

  2-methoxy-1,4-bis(methoxymethoxy)benzene 在 palladium on activated charcoal 4-二甲氨基吡啶 、 三甲基氯硅烷 、 硝酸铵 、 四丁基氟化铵 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸酐 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 7.63h， 生成 methyl 3-chloro-2-[2-(2,5-dihydroxy-4-methoxyphenylcarbamoyl)ethyl]-4,6-dihydroxybenzoate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Radicicol and Geldanamycin Chimera, Radamide

  摘要：

  A chimera composed of the natural products radicicol and geldanamycin has been prepared through an amide linkage connecting the resorcinol moiety of radicicol to the quinone ring of geldanamycin. The inhibitory activity of these compounds was determined by their ability to inhibit Hsp90's inherent ATPase activity along with degradation of the Hsp90 client protein, HER-2 in MCF-7 breast cancer cells.

  DOI：

  10.1021/ol048266o

文献信息

• Heat shock protein 90 inhibitors
  申请人：Blagg Brian

  公开号：US20060089495A1

  公开（公告）日：2006-04-27

  Novel compounds useful for inhibiting the 90 kDa heat shock proteins containing a quinone-like moiety and a di-hydroxy phenol like moiety, similar to geldanamycin and radicicol.

  新型化合物对抑制含有类似醌类结构和二羟基酚类结构的90千道尔顿热休克蛋白具有用途，类似于格尔德霉素和拉迪考尔。
• Synthesis and Evaluation of Radamide Analogues, A Chimera of Radicicol and Geldanamycin
  作者：M. Kyle Hadden、Brian S. J. Blagg

  DOI：10.1021/jo900278g

  日期：2009.7.3

  Previously, we reported the Hsp90 inhibitory activity of radamide, an open chain amide chimera of geldanamycin and radicicol. Attempts to further expand upon structure-activity relationships for this class of Hsp90 inhibitors led to the preparation of a series of radamide analogues focused on differing tether lengths and quinone mimics. In addition, the cup-shaped conformation adopted by the two natural products when bound to the Hsp90 N-terminal ATP binding pocket suggests that conformationally biased compounds may demonstrate improved binding and inhibition. The preparation and evaluation of radamide analogues with cisltrans alpha,beta-unsaturated amides yielded compounds that exhibit improved antiproliferative activity. In addition, several analogues demonstrated the ability to induce degradation of Hsp90-dependent oncogenic signaling proteins in vitro, a hallmark of Hsp90 N-terminal inhibition.
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.
• Design, Synthesis, and Evaluation of a Radicicol and Geldanamycin Chimera, Radamide
  作者：Randell C. Clevenger、Brian S. J. Blagg

  DOI：10.1021/ol048266o

  日期：2004.11.1

  A chimera composed of the natural products radicicol and geldanamycin has been prepared through an amide linkage connecting the resorcinol moiety of radicicol to the quinone ring of geldanamycin. The inhibitory activity of these compounds was determined by their ability to inhibit Hsp90's inherent ATPase activity along with degradation of the Hsp90 client protein, HER-2 in MCF-7 breast cancer cells.