(1R,2R,4R)-4-methyl-1,2-cyclohexanediamine | 1246967-36-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R,4R)-4-methyl-1,2-cyclohexanediamine
• 英文别名: (1R,2R,4R)-4-methylcyclohexane-1,2-diamine
• CAS: 1246967-36-1
• 化学式: C₇H₁₆N₂
• 分子量: 128.217
• InChiKey: KKYGOXSPNXROTG-FSDSQADBSA-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：

  potassium tetrachloroplatinate(II) 、 (1R,2R,4R)-4-methyl-1,2-cyclohexanediamine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 为溶剂， 反应 4.0h， 以6.8 mg的产率得到equatorial cis-[4-methyl-trans-(+/-)-1,2-cyclohexenediamine]dichloride platinum(II)
  参考文献：
  名称：

  环修饰对奥沙利铂类化合物引起的核仁应力的影响**

  摘要：

  对在 1,2-二氨基环己烷 (DACH) 配体的 4 位修饰的 Pt(II) 化合物进行有限的结构-功能研究表明，具有甲基、乙基和丙基取代基的化合物诱导核仁应力，而具有异丙基和乙酰胺取代基没有。这些结果表明 Pt(II) 化合物对核仁应激的诱导更为复杂。

  DOI：

  10.1002/cbic.202200130
• 作为产物：
  描述：

  (1R,2R,4R)-4-methyl-1,2-cyclohexanediaminium L-tartrate 在 sodium hydroxide 作用下， 生成 (1R,2R,4R)-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

文献信息

• Methyl-substituted trans-1,2-cyclohexanediamines as new ligands for oxaliplatin-type complexes
  作者：Ladislav Habala、Claudia Dworak、Alexey A. Nazarov、Christian G. Hartinger、Sergey A. Abramkin、Vladimir B. Arion、Wolfgang Lindner、Mathea S. Galanski、Bernhard K. Keppler

  DOI：10.1016/j.tet.2007.10.069

  日期：2008.1

  different synthetic routes lead (i) by the synthesis of the compound via ortho-bromination of a substituted cyclohexanone followed by reaction with hydroxylamine and reduction by hydrogen, (ii) by addition of azide to cyclohexene mediated by manganese(III) acetate and reduction by hydrogen, or (iii) by trans-dihydroxylation of cyclohexene, and subsequent conversion into the respective mesylate or tosylate

  提出了三种不同的途径合成取代的反式-（±）-1,2-环己二胺作为奥沙利铂类化合物的新配体。不同的合成路线导致（i）通过取代环己酮的邻溴化合成化合物，然后与羟胺反应并用氢还原，（ii）通过将乙酸锰（III）介导的叠氮化物加到环己烯中并还原通过氢，或（iii）通过环己烯的反二羟基化，然后转化成各自的甲磺酸酯或甲苯磺酸酯，随后被叠氮化物取代，和在4-甲基-反式的情况下还原-（±）-1,2-环己二胺分别优选在赤道上，主要在轴向上或仅在赤道上或轴向上定向的4-甲基。
• [EN] MONOMALEIMIDE-FUNCTIONALIZED PLATINUM COMPOUNDS FOR CANCER THERAPY<br/>[FR] COMPOSÉS DE PLATINE À FONCTION MONOMALÉIMIDE POUR LE TRAITEMENT DU CANCER
  申请人：UNIV WIEN MED

  公开号：WO2017097986A1

  公开（公告）日：2017-06-15

  The present invention relates to novel monomaleimide-functionalized platinum compounds of formula (I), including in particular novel monomaleimide-functionalized oxaliplatin and carboplatin derivatives, as well as their use as medicaments, particularly for the treatment or prevention of cancer.

  本发明涉及一种新型单马来酰亚胺官能化铂化合物，其化学式为(I)，其中包括新型单马来酰亚胺官能化奥沙利铂和卡铂衍生物，以及它们作为药物的用途，特别是用于治疗或预防癌症。
• Monomaleimide-functionalized platinum compounds for cancer therapy
  申请人：Medizinische Universität Wien

  公开号：US10723748B2

  公开（公告）日：2020-07-28

  The present invention relates to novel monomaleimide-functionalized platinum compounds of formula (I), including in particular novel monomaleimide-functionalized oxaliplatin and carboplatin derivatives, as well as their use as medicaments, particularly for the treatment or prevention of cancer.

  本发明涉及新型单马来酰亚胺官能化的式（I）铂化合物，尤其包括新型单马来酰亚胺官能化的奥沙利铂和卡铂衍生物，以及它们作为药物的用途，特别是用于治疗或预防癌症。
• MONOMALEIMIDE-FUNCTIONALIZED PLATINUM COMPOUNDS FOR CANCER THERAPY
  申请人：Medizinische Universität Wien

  公开号：EP3386997A1

  公开（公告）日：2018-10-17