(6S)-N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride | 1321624-39-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (6S)-N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride
• 英文别名: [(6S)-2,6-dimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]-(4-methoxyphenyl)-methylazanium;chloride
• CAS: 1321624-39-8
• 化学式: C₁₇H₂₁N₃O*ClH
• 分子量: 319.834
• InChiKey: NDXKJZRXESTNKZ-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-(S)-3-methylhexanedioic acid 在 盐酸 、 硫酸 、 potassium tert-butylate 、 sodium 、 三氯氧磷 作用下， 以 水 、 异丙醇 、 甲苯 、 叔丁醇 为溶剂， 反应 14.0h， 生成 (6S)-N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium Chloride as Potent Cytotoxic Antitubulin Agents

  摘要：

  (R,S)-1 is a potent antimitotic compound. (R)-1 center dot HCl and (S)-1 center dot HCl were synthesized from (R)- and (S)-3-methyladipic acid. Both enantiomers were potent inhibitors of cell proliferation and caused cellular microtubule loss and mitotic arrest. They inhibited purified tubulin assembly and the binding of [H-3]colchicine to tubulin, with (S)-1 being about twice as potent. Cytotoxicity against 60 tumor cell lines, however, indicated that the (S)-isomer was 10- to 88-fold more potent than the (R)-isomer.

  DOI：

  10.1021/jm2007722

文献信息

• Synthesis and Biological Activities of (<i>R</i>)- and (<i>S</i>)-<i>N</i>-(4-Methoxyphenyl)-<i>N</i>,2,6-trimethyl-6,7-dihydro-5<i>H</i>-cyclopenta[<i>d</i>]pyrimidin-4-aminium Chloride as Potent Cytotoxic Antitubulin Agents
  作者：Aleem Gangjee、Ying Zhao、Ernest Hamel、Cara Westbrook、Susan L. Mooberry

  DOI：10.1021/jm2007722

  日期：2011.9.8

  (R,S)-1 is a potent antimitotic compound. (R)-1 center dot HCl and (S)-1 center dot HCl were synthesized from (R)- and (S)-3-methyladipic acid. Both enantiomers were potent inhibitors of cell proliferation and caused cellular microtubule loss and mitotic arrest. They inhibited purified tubulin assembly and the binding of [H-3]colchicine to tubulin, with (S)-1 being about twice as potent. Cytotoxicity against 60 tumor cell lines, however, indicated that the (S)-isomer was 10- to 88-fold more potent than the (R)-isomer.