meridoquin | 1342901-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: meridoquin
• 英文别名: 4-(6-chloro-1H-indol-3-yl)-N,N-diethyl-pyrimidin-2-amine；4-(6-chloro-1H-indol-3-yl)-N,N-diethylpyrimidin-2-amine
• CAS: 1342901-70-5
• 化学式: C₁₆H₁₇ClN₄
• 分子量: 300.791
• InChiKey: SKDZMQCQPCAWQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯吲哚 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 叔丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 正戊烷 、 苯 为溶剂， 反应 25.33h， 生成 meridoquin
  参考文献：
  名称：

  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs

  摘要：

  The marine invertebrate-derived meridianin A. the originally proposed structure for psammopemmin A. and several related 3-pyrimidylindole analogs were synthesized and subsequently investigated for central nervous system, antimalarial, and cytotoxic activity. A Suzuki coupling of an indoleborate ester to the pyrimidine electrophile was utilized to form the natural product and derivatives thereof. The 3-pyrimidineindoles were found to prevent radioligand binding to several CNS receptors and transporters, most notably, serotonin receptors (<0.2 mu M K-i for 5HT(2B)). Two compounds also inhibited the human malaria parasite Plasmodium falciparum (IC50 <50 mu M). Only the natural product was cytotoxic toward A549 cells (IC50 = 15 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.033

文献信息

• CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs
  作者：Matthew D. Lebar、Kristopher N. Hahn、Tina Mutka、Patrick Maignan、James B. McClintock、Charles D. Amsler、Alberto van Olphen、Dennis E. Kyle、Bill J. Baker

  DOI：10.1016/j.bmc.2011.08.033

  日期：2011.10

  The marine invertebrate-derived meridianin A. the originally proposed structure for psammopemmin A. and several related 3-pyrimidylindole analogs were synthesized and subsequently investigated for central nervous system, antimalarial, and cytotoxic activity. A Suzuki coupling of an indoleborate ester to the pyrimidine electrophile was utilized to form the natural product and derivatives thereof. The 3-pyrimidineindoles were found to prevent radioligand binding to several CNS receptors and transporters, most notably, serotonin receptors (<0.2 mu M K-i for 5HT(2B)). Two compounds also inhibited the human malaria parasite Plasmodium falciparum (IC50 <50 mu M). Only the natural product was cytotoxic toward A549 cells (IC50 = 15 mu M). (C) 2011 Elsevier Ltd. All rights reserved.