N-(2-amino-2-methylpropyl)-2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetamide;4-methylbenzenesulfonic acid | 1101829-42-8

• 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: N-(2-amino-2-methylpropyl)-2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetamide;4-methylbenzenesulfonic acid
• CAS: 1101829-42-8
• 化学式: C₇H₈O₃S*C₁₅H₂₈N₂O₃
• 分子量: 456.604
• InChiKey: OTCVTIKVIPIUGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-diamino-2-methylpropane mono-p-toluenesulfonate 、 2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以58%的产率得到N-(2-amino-2-methylpropyl)-2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetamide;4-methylbenzenesulfonic acid
  参考文献：
  名称：

  Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum

  摘要：

  Artemisinin-derived compounds play an integral role in current malaria chemotherapy. Given the virtual certainty of emerging resistance, we have investigated spiro-1,2-dioxolanes as an alternative scaffold. The endoperoxide functionality was generated by the SnCl(4)-mediated annulation of a bis-silylperoxide and an alkene. The first set of eight analogs gave EC(50) values of 50-150 nM against Plasmodium falciparum 3D7 and Dd2 strains, except for the carboxylic acid analog. A second series, synthesized by coupling a spiro-1,2-dioxolane carboxylic acid to four separate amines, afforded the most potent compound ( EC50 similar to 5 nM). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.083

文献信息

• Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum
  作者：Derek C. Martyn、Armando P. Ramirez、Meaghan J. Beattie、Joseph F. Cortese、Vishal Patel、Margaret A. Rush、K.A. Woerpel、Jon Clardy

  DOI：10.1016/j.bmcl.2008.10.083

  日期：2008.12

  Artemisinin-derived compounds play an integral role in current malaria chemotherapy. Given the virtual certainty of emerging resistance, we have investigated spiro-1,2-dioxolanes as an alternative scaffold. The endoperoxide functionality was generated by the SnCl(4)-mediated annulation of a bis-silylperoxide and an alkene. The first set of eight analogs gave EC(50) values of 50-150 nM against Plasmodium falciparum 3D7 and Dd2 strains, except for the carboxylic acid analog. A second series, synthesized by coupling a spiro-1,2-dioxolane carboxylic acid to four separate amines, afforded the most potent compound ( EC50 similar to 5 nM). (C) 2008 Elsevier Ltd. All rights reserved.