(E)-N1-(3,7-二甲基辛-2,6-二烯-1-基)乙烷-1,2-二胺 | 1227090-46-1

• 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
• 中文名称: (E)-N1-(3,7-二甲基辛-2,6-二烯-1-基)乙烷-1,2-二胺
• 英文名称: N'-geranylethane-1,2-diamine
• 英文别名: 1,2-Ethanediamine, N1-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-；N'-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine
• CAS: 1227090-46-1
• 化学式: C₁₂H₂₄N₂
• 分子量: 196.336
• InChiKey: JCIITWXLJRJGNM-KPKJPENVSA-N

物化性质

• 沸点：
  296.0±28.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N1-(3,7-二甲基辛-2,6-二烯-1-基)乙烷-1,2-二胺 在 硫酸 、 sodium chloride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以1.6g的产率得到N-geranylethane-1,2-diamine dihydochloride
  参考文献：
  名称：

  The terpenic diamine GIB24 inhibits the growth of Trypanosoma cruzi epimastigotes and intracellular amastigotes, with proteomic analysis of drug-resistant epimastigotes

  摘要：

  The effect of N-geranyl-ethane-1,2-diamine dihydochloride (GIB24), a synthetic diamine, was assayed against different developmental forms of the parasitic protozoan Trypanosoma cruzi (strain Dm28c). The compound was effective against culture epimastigote forms (IC50/24h = 5.64 pM; SI = 16.4) and intracellular amastigotes (IC50/24h = 12.89 mu M; SI = 7.18), as detected by the MTT methodology and by cell counting, respectively. Incubation of epimastigotes for 6h with 6 mu M GIB24 (IC50/24h value) resulted in significant dissipation of the mitochondrial membrane potential, prior to permeabilization of the plasma membrane. Rounded epimastigotes with cell size reduction were observed by scanning electron microscopy. These morpho-physiological changes induced by GIB24 suggest an incidental death process. Treatment of infected Vero cells did not prevent the intracellular amastigotes from completing the intracellular cycle. However, there was a decrease in the number of released parasites, increasing the ratio amastigotes/trypomastigotes. Proteomic analysis of 15 mu M GIB24 resistant epimastigotes indicated that the compound acts mainly on mitochondrial components involved in the Krebs cycle and in maintaining the oxidative homeostasis of the parasites. Our data suggest that GIB24 is active against the main morphological forms of T. cruzi.

  DOI：

  10.1016/j.cbi.2020.109165
• 作为产物：
  描述：

  香叶醇 在 三溴化磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-N1-(3,7-二甲基辛-2,6-二烯-1-基)乙烷-1,2-二胺
  参考文献：
  名称：

  The terpenic diamine GIB24 inhibits the growth of Trypanosoma cruzi epimastigotes and intracellular amastigotes, with proteomic analysis of drug-resistant epimastigotes

  摘要：

  The effect of N-geranyl-ethane-1,2-diamine dihydochloride (GIB24), a synthetic diamine, was assayed against different developmental forms of the parasitic protozoan Trypanosoma cruzi (strain Dm28c). The compound was effective against culture epimastigote forms (IC50/24h = 5.64 pM; SI = 16.4) and intracellular amastigotes (IC50/24h = 12.89 mu M; SI = 7.18), as detected by the MTT methodology and by cell counting, respectively. Incubation of epimastigotes for 6h with 6 mu M GIB24 (IC50/24h value) resulted in significant dissipation of the mitochondrial membrane potential, prior to permeabilization of the plasma membrane. Rounded epimastigotes with cell size reduction were observed by scanning electron microscopy. These morpho-physiological changes induced by GIB24 suggest an incidental death process. Treatment of infected Vero cells did not prevent the intracellular amastigotes from completing the intracellular cycle. However, there was a decrease in the number of released parasites, increasing the ratio amastigotes/trypomastigotes. Proteomic analysis of 15 mu M GIB24 resistant epimastigotes indicated that the compound acts mainly on mitochondrial components involved in the Krebs cycle and in maintaining the oxidative homeostasis of the parasites. Our data suggest that GIB24 is active against the main morphological forms of T. cruzi.

  DOI：

  10.1016/j.cbi.2020.109165

文献信息

• Novel Linear Diamine Disubstituted Polycyclic ‘Cage’ Derivatives as Potential Antimycobacterial Candidates
  作者：Oluseye K. Onajole、Sphelele Sosibo、Patrick Govender、Thavendran Govender、Paul D. van Helden、Glenn E. M. Maguire、Kata Mlinarić-Majerski、Ian Wiid、Hendrik G. Kruger

  DOI：10.1111/j.1747-0285.2011.01242.x

  日期：2011.12

  5, 7 and SQ109 were selected for further screening against, multi‐drug resistant, (R1097) and extensively drug resistant, (X149) strains of tuberculosis. Compound 5 showed anti‐TB activity of a MIC = 1 μm against multi‐drug resistant strain (R1097) and <1 μM against extensively drug resistant strain (X149) while compound 7 and SQ109 showed excellent anti‐TB activity against both drug‐resistant strains

  作为一项正在进行的开发高效抗结核治疗药物的项目的一部分，合成了一系列新型多环“笼”四胺，并筛选了针对肺结核H 37 Rv菌株的体外抗结核活性。在这项研究中使用了三个双取代的多环部分，即五环癸烷，五环十一烷和三环癸烷。化合物5和7表现出相似的活性SQ109以1μ一个MIC米而化合物4，6和8在1
• 取代缩胺硫脲类化合物及其在抗结核杆菌中的应用
  申请人：国科维思（北京）药物研究有限公司

  公开号：CN111362868A

  公开（公告）日：2020-07-03

  本发明属于药物化学领域，涉及下式(I)缩胺硫脲类化合物，其几何异构体及其药物上可接受的盐和/或其溶剂化物和/或其水合物，及含有此化合物的药物组合物，用于治疗结核杆菌方面的用途。
• Structure, <i>In Vivo</i> Detection, and Antibacterial Activity of Metabolites of SQ109, an Anti-Infective Drug Candidate
  作者：Satish R. Malwal、Matthew D. Zimmerman、Nadine Alvarez、Jansy P. Sarathy、Véronique Dartois、Carol A. Nacy、Eric Oldfield

  DOI：10.1021/acsinfecdis.1c00259

  日期：2021.8.13

  it has been proposed that some of its metabolites might be responsible for its activity against TB. Here, we synthesized six potential P450 metabolites of SQ109 and used these as well as 10 other likely metabolites as standards in a mass spectrometry study of M. tuberculosis-infected rabbits treated with SQ109, in addition to testing all 16 putative metabolites for antibacterial activity. We found that

  SQ109 是治疗结核病 (TB) 的候选药物。它被认为主要针对结核分枝杆菌中的蛋白质 MmpL3 ，但它也抑制其他一些细菌的生长。SQ109 由肝脏代谢，有人提出它的一些代谢物可能是其抗结核病活性的原因。在这里，我们合成了 SQ109 的 6 种潜在 P450 代谢物，并将这些以及 10 种其他可能的代谢物用作用 SQ109 治疗的结核分枝杆菌感染兔的质谱研究的标准，此外还测试了所有 16 种推定代谢物的抗菌活性。我们发现肺组织中只有两种主要代谢物：SQ109 的羟基金刚烷基类似物和N'-金刚烷基乙二胺。这些或测试的其他潜在代谢物均未抑制结核分枝杆菌或耻垢分枝杆菌、枯草芽孢杆菌或大肠杆菌的生长，因此 SQ109 代谢物不太可能有助于其抗菌活性。因此，在兔 TB 模型中，非代谢的 SQ109 在组织中逐渐积累到治疗水平会导致良好的疗效。我们的结果还提供了关于 SQ109 如何与其目标 MmpL3
• ETHYLENEDIAMINE COMPOUND AND USE THEREOF
  申请人：Academy Of Military Medical Sciences

  公开号：EP3904330A1

  公开（公告）日：2021-11-03

  The present invention relates to the field of medicinal chemistry, and relates to an ethylenediamine compound represented by Formula A, pharmaceutically acceptable salts, stereoisomers, tautomers or isomer mixtures, hydrates thereof, solvates thereof, or prodrugs thereof, and use thereof in the treatment of tuberculosis.

  本发明涉及药物化学领域，涉及一种由式 A 代表的乙二胺化合物、药学上可接受的盐、立体异构体、同分异构体或异构体混合物、其水合物、其溶物或其原药，以及其在治疗结核病中的用途。
• Use of polyaminoisoprenyl derivatives in antibiotic or antiseptic treatment
  申请人：UNIVERSITE D'AIX-MARSEILLE

  公开号：US10562842B2

  公开（公告）日：2020-02-18

  The present invention relates to the use of polyaminoisoprenyl derivatives in antibiotic or antiseptic treatment of bacteria including those presenting multiple drug resistance (MDR), in particular as efflux pump inhibitors. It also relates to novel polyaminoisoprenyl derivatives, compositions comprising the same, process for preparing the same, and use thereof in antibiotic or antiseptic treatment.

  本发明涉及聚氨基异戊烯基衍生物在抗生素或防腐剂治疗细菌（包括具有多重耐药性（MDR）的细菌）中的用途，特别是作为外排泵抑制剂。本发明还涉及新型聚氨基异戊烯基衍生物、包含聚氨基异戊烯基衍生物的组合物、制备聚氨基异戊烯基衍生物的工艺及其在抗生素或防腐剂治疗中的用途。