Carbonic acid 4-amino-2,6-dimethoxy-phenyl ester benzyl ester | 176915-27-8

• 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: Carbonic acid 4-amino-2,6-dimethoxy-phenyl ester benzyl ester
• CAS: 176915-27-8
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: ITLBGNXMZWVGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid 4-amino-2,6-dimethoxy-phenyl ester benzyl ester 在 palladium on activated charcoal 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3aS,4R,10R)-10-(4-Hydroxy-3,5-dimethoxy-phenyl)-4-(4-hydroxy-3,5-dimethoxy-phenylamino)-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-1-one
  参考文献：
  名称：

  Inhibition of DNA Topoisomerase II by Azaelliptitoxins Functionalized in the Variable Substituent Domain

  摘要：

  A series of novel C-11-substituted derivatives of azaelliptitoxin (azatoxin) have been synthesized and tested for their inhibitory activity against human DNA topoisomerase II. Incorporation of a C-11 polyamine pr amine resulted in an increase in the intercalation properties of the drug and a decrease of topoisomerase II activity. The structure-activity relationship (SAR) profile of the nonintercalating C-11 anilino azatoxin class follows the SAR of the (anilino)acridine family. 11-(4-Cyanoanilino)azatoxin (14) was found to be the most active analog in this series, exhibiting similar to 10-fold higher activity than azatoxin 12 and etoposide.

  DOI：

  10.1021/jm9508806
• 作为产物：
  描述：

  1,2,3-三甲氧基-5-硝基苯 在 氢氧化钾 、 TEA 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 Carbonic acid 4-amino-2,6-dimethoxy-phenyl ester benzyl ester
  参考文献：
  名称：

  Inhibition of DNA Topoisomerase II by Azaelliptitoxins Functionalized in the Variable Substituent Domain

  摘要：

  A series of novel C-11-substituted derivatives of azaelliptitoxin (azatoxin) have been synthesized and tested for their inhibitory activity against human DNA topoisomerase II. Incorporation of a C-11 polyamine pr amine resulted in an increase in the intercalation properties of the drug and a decrease of topoisomerase II activity. The structure-activity relationship (SAR) profile of the nonintercalating C-11 anilino azatoxin class follows the SAR of the (anilino)acridine family. 11-(4-Cyanoanilino)azatoxin (14) was found to be the most active analog in this series, exhibiting similar to 10-fold higher activity than azatoxin 12 and etoposide.

  DOI：

  10.1021/jm9508806