N¹,N²-bis(4-isopropylbenzyl)ethane-1,2-diamine | 859340-32-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N¹,N²-bis(4-isopropylbenzyl)ethane-1,2-diamine
• 英文别名: N,N'-bis[(4-isopropylphenyl)methyl]ethane-1,2-diamine；N,N'-bis[(4-propan-2-ylphenyl)methyl]ethane-1,2-diamine
• CAS: 859340-32-2
• 化学式: C₂₂H₃₂N₂
• 分子量: 324.509
• InChiKey: PGLMSKMAIHYTBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N¹,N²-bis(4-isopropylbenzyl)ethane-1,2-diamine 在 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 2-(chloromethyl)-1,4-bis(4-isopropylbenzyl)piperazine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1

  摘要：

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.

  DOI：

  10.1016/j.bmc.2019.02.051
• 作为产物：
  描述：

  N,N-bis(4-isopropylbenzylidene)ethane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N¹,N²-bis(4-isopropylbenzyl)ethane-1,2-diamine
  参考文献：
  名称：

  制备一系列带有N-杂环卡宾配体的Ru（ii）配合物，用于芳族酮的催化转移氢化†

  摘要：

  [RuCl 2（p- Cymene）2与Ag- N-杂环卡宾（NHC）配合物的反应产生了一系列[[ p- Cymene）Ru（NHC）]配合物（2a–f），所有合成的化合物均经过了表征通过元素分析，NMR光谱和X射线晶体学测定2a的分子结构，所有配合物均已作为芳香族酮转移加氢的催化剂进行了测试，显示出优异的活性。

  DOI：

  10.1039/c1dt11203a

文献信息

• Preparation of a series of Ru(<scp>ii</scp>) complexes with N-heterocyclic carbeneligands for the catalytic transfer hydrogenation of aromatic ketones
  作者：Nevin Gürbüz、Emine Özge Özcan、İsmail Özdemir、Bekir Çetinkaya、Onur Şahin、Orhan Büyükgüngör

  DOI：10.1039/c1dt11203a

  日期：——

  [RuCl2(p-cymene]2 with Ag–N-heterocyclic carbene (NHC) complexes yields a series of [(p-cymene)Ru(NHC)] complexes (2a–f). All synthesised compounds were characterized by elemental analysis, NMR spectroscopy and the molecular structure of 2a was determined by X-ray crystallography. All complexes have been tested as catalysts for the transfer hydrogenation of aromatic ketones, showing excellent activity in this reaction

  [RuCl 2（p- Cymene）2与Ag- N-杂环卡宾（NHC）配合物的反应产生了一系列[[ p- Cymene）Ru（NHC）]配合物（2a–f），所有合成的化合物均经过了表征通过元素分析，NMR光谱和X射线晶体学测定2a的分子结构，所有配合物均已作为芳香族酮转移加氢的催化剂进行了测试，显示出优异的活性。
• Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1
  作者：Safaa M. Kishk、Kirsty J. McLean、Sakshi Sood、Mohamed A. Helal、Mohamed S. Gomaa、Ismail Salama、Samia M. Mostafa、Luiz Pedro S. de Carvalho、Andrew W. Munro、Claire Simons

  DOI：10.1016/j.bmc.2019.02.051

  日期：2019.4

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.