(1S,2S,4S)-4-methyl-1,2-cyclohexanediamine | 1246967-39-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S,4S)-4-methyl-1,2-cyclohexanediamine
• 英文别名: (1S,2S,4S)-4-methylcyclohexane-1,2-diamine
• CAS: 1246967-39-4
• 化学式: C₇H₁₆N₂
• 分子量: 128.217
• InChiKey: KKYGOXSPNXROTG-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯甲酸苄酯 、 (1S,2S,4S)-4-methyl-1,2-cyclohexanediamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以0.76 g的产率得到N,N'-bis(benzyloxycarbonyl)-4-methyl-trans-(+/-)-1,2-cyclohexanedicarbamate
  参考文献：
  名称：

  {(1R,2R,4R)-4-Methyl-1,2-cyclohexanediamine}oxalatoplatinum(II): A Novel Enantiomerically Pure Oxaliplatin Derivative Showing Improved Anticancer Activity in Vivo

  摘要：

  Novel derivatives of the clinically established anticancer drug oxaliplatin were synthesized. Cytotoxicity of the compounds was studied in six human cancer cell lines by means of the MTT assay. Additionally, most promising complexes were also investigated in cisplatin- and oxaliplatin-resistant human cancer cell models. The therapeutic efficacy in vivo was studied in the murine L1210 leukemia model. Most remarkably, {(1R,2R,4R)-4-methyl-1,2-cyclohexanediamine}oxalatoplatinum(II), comprising an equatorial methyl substituent at position 4 of the cyclohexane ring, was as potent as oxaliplatin in vitro but distinctly more effective in the L1210 model in vivo at the optimal dose. The advantage observed in the in vivo situation was mainly based on a more favorable therapeutic index. The maximum tolerated dose of the novel analogue was higher than that of oxaliplatin and caused a greater increase in life span (>200% versus 152%), with more animals experiencing long-term survival (5/6 versus 2/6). These data support further (pre)clinical development of the methyl-substituted oxaliplatin analogue with improved anticancer activity.

  DOI：

  10.1021/jm100953c
• 作为产物：
  描述：

  (1S,2S,4S)-4-methyl-1,2-cyclohexanediaminium D-tartrate 在 sodium hydroxide 作用下， 生成 (1S,2S,4S)-4-methyl-1,2-cyclohexanediamine
  参考文献：
  名称：

  {(1R,2R,4R)-4-Methyl-1,2-cyclohexanediamine}oxalatoplatinum(II): A Novel Enantiomerically Pure Oxaliplatin Derivative Showing Improved Anticancer Activity in Vivo

  摘要：

  Novel derivatives of the clinically established anticancer drug oxaliplatin were synthesized. Cytotoxicity of the compounds was studied in six human cancer cell lines by means of the MTT assay. Additionally, most promising complexes were also investigated in cisplatin- and oxaliplatin-resistant human cancer cell models. The therapeutic efficacy in vivo was studied in the murine L1210 leukemia model. Most remarkably, {(1R,2R,4R)-4-methyl-1,2-cyclohexanediamine}oxalatoplatinum(II), comprising an equatorial methyl substituent at position 4 of the cyclohexane ring, was as potent as oxaliplatin in vitro but distinctly more effective in the L1210 model in vivo at the optimal dose. The advantage observed in the in vivo situation was mainly based on a more favorable therapeutic index. The maximum tolerated dose of the novel analogue was higher than that of oxaliplatin and caused a greater increase in life span (>200% versus 152%), with more animals experiencing long-term survival (5/6 versus 2/6). These data support further (pre)clinical development of the methyl-substituted oxaliplatin analogue with improved anticancer activity.

  DOI：

  10.1021/jm100953c