11-(4-(ethylcarboxy)phenyl)cinchonine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: 11-(4-(ethylcarboxy)phenyl)cinchonine
• 化学式: C₂₈H₃₀N₂O₃
• 分子量: 442.558
• InChiKey: MKSXYWBZRZBLAV-ABMRFVCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  辛可宁 、 4-溴苯甲酸乙酯 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以65%的产率得到11-(4-(ethylcarboxy)phenyl)cinchonine
  参考文献：
  名称：

  Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum

  摘要：

  Plasmodium falciparum, the deadliest malarial parasite species, has developed resistance against nearly all man-made antimalarial drugs within the past century. However, quinine (QN), the first antimalarial drug, remains efficacious worldwide. Some chloroquine resistant (CQR) P. falciparum strains or isolates show mild cross resistance to QN, but many do not. Further optimization of QN may provide a well-tolerated therapy with improved activity versus CQR malaria. Thus, using the Heck reaction, we have pursued a structure-activity relationship study, including vinyl group modifications of QN. Certain derivatives show good antiplasmodial activity in QN-resistant and QN-sensitive strains, with lower IC50 values relative to QN. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.042

文献信息

• Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum
  作者：Theresa Dinio、Alexander P. Gorka、Andrew McGinniss、Paul D. Roepe、Jeremy B. Morgan

  DOI：10.1016/j.bmc.2012.03.042

  日期：2012.5

  Plasmodium falciparum, the deadliest malarial parasite species, has developed resistance against nearly all man-made antimalarial drugs within the past century. However, quinine (QN), the first antimalarial drug, remains efficacious worldwide. Some chloroquine resistant (CQR) P. falciparum strains or isolates show mild cross resistance to QN, but many do not. Further optimization of QN may provide a well-tolerated therapy with improved activity versus CQR malaria. Thus, using the Heck reaction, we have pursued a structure-activity relationship study, including vinyl group modifications of QN. Certain derivatives show good antiplasmodial activity in QN-resistant and QN-sensitive strains, with lower IC50 values relative to QN. (C) 2012 Elsevier Ltd. All rights reserved.