(R)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-2-(1-(phenylamino)ethylidene)dibenzo[b,d]furan-1,3(2H,9bH)-dione | 454464-40-5

• 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: (R)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-2-(1-(phenylamino)ethylidene)dibenzo[b,d]furan-1,3(2H,9bH)-dione
• CAS: 454464-40-5
• 化学式: C₂₄H₂₁NO₆
• 分子量: 419.4
• InChiKey: XPFSFYYQNTXFRI-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+)-usnic acid 、 苯胺 以 乙醇 为溶剂， 反应 3.0h， 生成 (R)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-2-(1-(phenylamino)ethylidene)dibenzo[b,d]furan-1,3(2H,9bH)-dione
  参考文献：
  名称：

  Tyrosyl-DNA Phosphodiesterase 1 Inhibitors: Usnic Acid Enamines Enhance the Cytotoxic Effect of Camptothecin

  摘要：

  Tyrosyl-DNA phosphodiesterase 1 (TDP1) is a repair enzyme for stalled DNA-topoisomerase 1 (Topl) cleavage complexes and other 3'-end DNA lesions. TDP1 is a perspective target for anticancer therapy based on Topl-poison-mediated DNA damage. Several novel usnic acid derivatives with an enamine moiety have been synthesized and tested as inhibitors of TDP1. The enamines of usnic acid showed IC50 values in the range of 0.16 to 2.0 mu M. These compounds revealed moderate cytotoxicity against human tumor MCF-7 cells. These new compounds enhanced the cytotoxicity of the established Topl poison camptothecin by an order of magnitude.

  DOI：

  10.1021/acs.jnatprod.6b00979

文献信息

• Tyrosyl-DNA Phosphodiesterase 1 Inhibitors: Usnic Acid Enamines Enhance the Cytotoxic Effect of Camptothecin
  作者：Alexandra Zakharenko、Olga Luzina、Olga Koval、Dmitry Nilov、Irina Gushchina、Nadezhda Dyrkheeva、Vytas Švedas、Nariman Salakhutdinov、Olga Lavrik

  DOI：10.1021/acs.jnatprod.6b00979

  日期：2016.11.23

  Tyrosyl-DNA phosphodiesterase 1 (TDP1) is a repair enzyme for stalled DNA-topoisomerase 1 (Topl) cleavage complexes and other 3'-end DNA lesions. TDP1 is a perspective target for anticancer therapy based on Topl-poison-mediated DNA damage. Several novel usnic acid derivatives with an enamine moiety have been synthesized and tested as inhibitors of TDP1. The enamines of usnic acid showed IC50 values in the range of 0.16 to 2.0 mu M. These compounds revealed moderate cytotoxicity against human tumor MCF-7 cells. These new compounds enhanced the cytotoxicity of the established Topl poison camptothecin by an order of magnitude.