(4-Amino-2-methoxyphenyl) benzyl carbonate | 176915-26-7

• 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: (4-Amino-2-methoxyphenyl) benzyl carbonate
• CAS: 176915-26-7
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: NOYQRUBQOQNICM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-Amino-2-methoxyphenyl) benzyl carbonate 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 (10R,15S,16R)-10-(4-hydroxy-3,5-dimethoxyphenyl)-16-(4-hydroxy-3-methoxyanilino)-13-oxa-8,11-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraen-12-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：

  4-硝基愈创木酚 在 TEA 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (4-Amino-2-methoxyphenyl) benzyl carbonate
  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